Faculty Appointments
Research Associate Professor of Biochemistry
Education
Ph.D., Organic Chemistry, Shinshu University, Nagano, JapanM.S., Chemistry, University of Dhaka, Dhaka, BangladeshB.S., Chemistry, University of Dhaka, Dhaka, Bangladesh
Office Address
Department of Biochemistry, Vanderbilt University School of Medicine
23rd at pearce
nashville, TN 37232-0146
23rd at pearce
nashville, TN 37232-0146
Research Description
Research Overview:
Jashim's research interests include development of targeted imaging agents for early detection for cancer and discovery of chemotherapeutic medicines for effective treatment of neoplastic diseases.
Major Accomplishments:
1. Discovery of Fluorocoxib Q, the 1st redox-activatable COX-2 inhibitor in 2022.
2. Discovery of Chemocoxib A, the 1st cytotoxic COX-2 inhibitor, 2016.
3. Discovery of Fluorocoxib A (Trade Mark: XenoLight), the 1st COX-2 targeted optical imaging agent, licensed to Perkin Elmar Pharma in 2014.
National Awards/Grants:
1. Phi Beta Psi Trust, National Research Award, AWD00001248 (Role: Principal Investigator/Program Director) 08/01/2023-08/15/2025, $140K.
2. National Institutes of Health (NIH), National Research Award, R01 CA260958-01A1 (Role: Multiple Principal Investigator/Program Director) 7/05/2021–06/30/2026, $3M.
Fellowships/Recognitions:
1. Recipient of the Financial Incentives Award from the Vanderbilt University School of Medicine Basic Sciences for securing two nationally competitive research grants.
Inclusive Date: 07/14/2023.
2. Recipient of OMICS Certificate of Recognition for research excellence in molecular imaging of COX-2 in cancer and inflammation at the International Conference on Radiology and Imaging in Chicago-North Shore.
Inclusive Date: 08/14/2013.
3. Recipient of Alberta Heritage Foundation for Medical Research (AHFMR) Post-doctoral Fellowship Award.
Inclusive Dates: 01/01/2002 – 12/31/2004.
4. Recipient of the Japanese Government (MONBUSHO) Graduate Scholarship Award, Department of Education, Japan.
Inclusive Dates: 09/02/1997 – 03/31/2001.
Professional Activities:
1. Ad Hoc Grant Reviewer, National Cancer Institute. Imaging Probe & Contrast Agents (IPCA) Study Section.
Inclusive Date: 02/2022 - Present
2. Ad Hoc Grant Reviewer, North Carolina Biotech Center Interdisciplinary Grant Program.
Inclusive Date: 03/2005 - Present
3. Chairman, Executive Committee, Network for Translational Research (NTR) Chemistry Core, National Institutes of Health.
Inclusive Dates: 02/2012 - 01/2013.
4. Member, Executive Committee, American Association of Cancer Research-American Chemical Society-Joint Meeting on Chemistry in Cancer Research, San Diego.
Inclusive Date: 01/2011 - 01/2012.
Patents:
1. Compounds and methods for imaging cancer (US0280543 A1 2018, US 10,792,377 B2 2020). Disclosed materials are diagnostic agents comprised of a radical and a fluorophore moiety. Disclosed technology methods for developing smart probes enable visualization of cells associated with cancer, inflammation, or disorders associated with carcinogenesis.
2. Composition and method for detecting hypoxia (US 179117 A1 2016, US10,695,446 B2 2020). Disclosed subject matter comprised diagnostic agent conjugated to a hypoxia marker moiety. Disclosed methods and compositions for diagnosing (i.e., by optical imaging) hypoxic cells and/or treating a disorder associated with hypoxia.
3. Fluorocoxib A loading into ROS-responsive nanoparticles (US0007723 A1 2017, US 10,105,455 B2 2018). Disclosed are compositions and methods for making and using the disclosed compositions. In a further aspect, disclosed are compositions that comprise a cyclooxygenase-2-selective therapeutic and/or diagnostic agent having a therapeutic and/or diagnostic agent conjugated to a NSAID drug; and a ROS-responsive nanoparticle.
4. Methods and compositions for diagnostic and therapeutic targeting of COX-2 (US 0254910 A1 2010, WO149456 A2 2007, WO149456 A3 2007, US 8,865,130 B2 2014). Disclosed subject matter provides compositions that selectively bind cyclooxygenase-2 and comprise a therapeutic and/or diagnostic moiety. Also, provided are methods for using the disclosed compositions for diagnosing (i.e. by imaging) a target cell and/or treating a disorder associated with a cyclooxygenase-2 biological activities.
Publications:
Asaduzzaman A, Thompson CC, Uddin MJ. Machine Learning Approaches for Skin Neoplasm Diagnosis. ACS Omega. 2024 Jul 7/8/2024; DOI: 10.1021/acsomega.4c03640.
Uddin MJ, et al. Polymeric Micellar Nanoparticles Enable Image-guided Drug Delivery in Solid Tumors. BioRxiv. 2024 Jun 6/7/2024; DOI: 10.1101/2024.06.07.598019.
Asaduzzaman A, Thompson CC, Uddin MJ. Machine Learning Approaches for Skin Neoplasm Diagnosis. BioRxiv. 2024 May 5/12/2024; DOI: 10.1101/2024.05.12.593773.
Uddin MJ, Niitsu H, Coffey RJ, Marnett LJ. Development of Pluoronic nanoparticles of fluorocoxib A for endoscopic fluorescence imaging of colonic adenomas [letter]. J Biomed Opt [print-electronic]. 2023 Apr; 28(4): 40501. PMID: 37091910, PMCID: PMC10118138, PII: 220308LR, DOI: 10.1117/1.JBO.28.4.040501, ISSN: 1560-2281.
Aleem AM, Kang W, Lin S, Milad M, Kingsley PJ, Crews BC, Uddin MJ, Rouzer CA, Marnett LJ. Ferroptosis Inhibitors Suppress Prostaglandin Synthesis in Lipopolysaccharide-Stimulated Macrophages. ACS Chem Biol [print-electronic]. 2023 Jan 1/13/2023; PMID: 36638351, DOI: 10.1021/acschembio.2c00869, ISSN: 1554-8937.
Uddin MJ, Lo JH, Oltman CG, Crews BC, Huda T, Liu J, Kingsley PJ, Lin S, Milad M, Aleem AM, Asaduzzaman A, McIntyre JO, Duvall CL, Marnett LJ. Discovery of a Redox-Activatable Chemical Probe for Detection of Cyclooxygenase-2 in Cells and Animals. ACS Chem Biol [print-electronic]. 2022 Jul 7/15/2022; 17(7): 1714-22. PMID: 35786843, DOI: 10.1021/acschembio.1c00961, ISSN: 1554-8937.
Winters ND, Bedse G, Astafyev AA, Patrick TA, Altemus M, Morgan AJ, Mukerjee S, Johnson KD, Mahajan VR, Uddin MJ, Kingsley PJ, Centanni SW, Siciliano CA, Samuels DC, Marnett LJ, Winder DG, Patel S. Targeting diacylglycerol lipase reduces alcohol consumption in preclinical models. J Clin Invest [print-electronic]. 2021 Jul 7/22/2021; 131(17): PMID: 34292886, PMCID: PMC8409586, PII: e146861, DOI: 10.1172/JCI146861, ISSN: 1558-8238.
Malerba P, Crews BC, Ghebreselasie K, Daniel CK, Jashim E, Aleem AM, Salam RA, Marnett LJ, Uddin MJ. Targeted Detection of Cyclooxygenase-1 in Ovarian Cancer. ACS Med Chem Lett. 2020 Oct 10/8/2020; 11(10): 1837-42. PMID: 33062161, PMCID: PMC7549111, DOI: 10.1021/acsmedchemlett.9b00280, ISSN: 1948-5875.
Uddin MJ, Xu S, Crews BC, Aleem AM, Ghebreselasie K, Banerjee S, Marnett LJ. Harmaline Analogs as Substrate-Selective Cyclooxygenase-2 Inhibitors. ACS Med Chem Lett. 2020 Oct 10/8/2020; 11(10): 1881-5. PMID: 33062168, PMCID: PMC7549255, DOI: 10.1021/acsmedchemlett.9b00555, ISSN: 1948-5875.
Uddin MJ, Vemulapalli A, Niitsu H, Crews BC, Oltman CG, Kingsley PJ, Kavanaugh TE, Bedingfield SK, Mcintyre JO, Milad M, Aleem AM, Coffey RJ, Duvall CL, Marnett LJ. Molecular Imaging of Inflammation in Osteoarthritis Using a Water-Soluble Fluorocoxib. ACS Med Chem Lett. 2020 Oct 10/8/2020; 11(10): 1875-80. PMID: 33062167, PMCID: PMC7549260, DOI: 10.1021/acsmedchemlett.9b00512, ISSN: 1948-5875.
Cekanova M, Pandey S, Olin S, Ryan P, Stokes JE, Hecht S, Martin-Jimenez T, Uddin MJ, Marnett LJ. Pharmacokinetic characterization of fluorocoxib D, a cyclooxygenase-2-targeted optical imaging agent for detection of cancer. J Biomed Opt. 2020 Aug; 25(8): PMID: 32860356, PMCID: PMC7456637, PII: JBO-200044R, DOI: 10.1117/1.JBO.25.8.086005, ISSN: 1560-2281.
Bourn J, Rathore K, Donnell R, White W, Uddin MJ, Marnett L, Cekanova M. Detection of carcinogen-induced bladder cancer by fluorocoxib A. BMC Cancer. 2019 Nov 11/27/2019; 19(1): 1152. PMID: 31775672, PMCID: PMC6882158, PII: 10.1186/s12885-019-6366-x, DOI: 10.1186/s12885-019-6366-x, ISSN: 1471-2407.
Uddin MJ, Wilson AJ, Crews BC, Malerba P, Uddin MI, Kingsley PJ, Ghebreselasie K, Daniel CK, Nickels ML, Tantawy MN, Jashim E, Manning HC, Khabele D, Marnett LJ. Discovery of Furanone-Based Radiopharmaceuticals for Diagnostic Targeting of COX-1 in Ovarian Cancer. ACS Omega [print-electronic]. 2019 May 5/31/2019; 4(5): 9251-61. PMID: 31172046, PMCID: PMC6545551, DOI: 10.1021/acsomega.9b01093, ISSN: 2470-1343.
Xu S, Uddin MJ, Banerjee S, Duggan K, Musee J, Kiefer JR, Ghebreselasie K, Rouzer CA, Marnett LJ. Conjugated Indomethacin Fluorescent Inhibitors Utilize the Membrane Binding Domain of Cyclooxygenase-2 to Accommodate the Tethered Moiety. J. Biol. Chem. 2019 Apr 4/30/2019; 294(22): 8690-8. PMID: 31000626.
Bourn J, Pandey S, Uddin MJ, Marnett LJ, Cekanova M. Detection of tyrosine kinase inhibitors-induced COX-2 expression in bladder cancer by fluorocoxib A. Oncotarget. 2019 Jan 1/29/2019; 10(48).
Shaheen SM, Azad AK, Rahman MM, Uddin MJ. A comparative transgene expression study between a protaplex and a rotaplex embedded lipid-nanoparticles in murine derived dendritic cell. J Interdiscipl Nanomed. 2018 Jul 7/10/2018; 0(0).
Cavener VS, Gaulden A, Pennipede D, Jagasia P, Uddin J, Marnett LJ, Patel S. Inhibition of Diacylglycerol Lipase Impairs Fear Extinction in Mice. Front Neurosci. 2018; 12: 479. PMID: 30108473, PMCID: PMC6080414, DOI: 10.3389/fnins.2018.00479, ISSN: 1662-4548.
Bedse G, Hartley ND, Neale E, Gaulden AD, Patrick TA, Kingsley PJ, Uddin MJ, Plath N, Marnett LJ, Patel S. Functional Redundancy Between Canonical Endocannabinoid Signaling Systems in the Modulation of Anxiety. Biol. Psychiatry [print-electronic]. 2017 Oct 10/1/2017; 82(7): 488-99. PMID: 28438413, PMCID: PMC5585044, PII: S0006-3223(17)31357-4, DOI: 10.1016/j.biopsych.2017.03.002, ISSN: 1873-2402.
Bluett RJ, Báldi R, Haymer A, Gaulden AD, Hartley ND, Parrish WP, Baechle J, Marcus DJ, Mardam-Bey R, Shonesy BC, Uddin MJ, Marnett LJ, Mackie K, Colbran RJ, Winder DG, Patel S. Endocannabinoid signalling modulates susceptibility to traumatic stress exposure. Nat Commun. 2017 Mar 3/28/2017; 8: 14782. PMID: 28348378, PMCID: PMC5379055, PII: ncomms14782, DOI: 10.1038/ncomms14782, ISSN: 2041-1723.
Foster DJ, Wilson JM, Remke DH, Mahmood MS, Uddin MJ, Wess J, Patel S, Marnett LJ, Niswender CM, Jones CK, Xiang Z, Lindsley CW, Rook JM, Conn PJ. Antipsychotic-like Effects of M4 Positive Allosteric Modulators Are Mediated by CB2 Receptor-Dependent Inhibition of Dopamine Release. Neuron [print-electronic]. 2016 Sep 9/21/2016; 91(6): 1244-52. PMID: 27618677, PII: S0896-6273(16)30509-8, DOI: 10.1016/j.neuron.2016.08.017, ISSN: 1097-4199.
Uddin MJ, Crews BC, Xu S, Ghebreselasie K, Daniel CK, Kingsley PJ, Banerjee S, Marnett LJ. Antitumor Activity of Cytotoxic Cyclooxygenase-2 Inhibitors. ACS Chem. Biol [print-electronic]. 2016 Sep 9/19/2016; PMID: 27588346, DOI: 10.1021/acschembio.6b00560, ISSN: 1554-8937.
Uddin MJ, Moore CE, Crews BC, Daniel CK, Ghebreselasie K, McIntyre JO, Marnett LJ, Jayagopal A. Fluorocoxib A enables targeted detection of cyclooxygenase-2 in laser-induced choroidal neovascularization. J Biomed Opt. 2016 Sep 9/1/2016; 21(9): 90503. PMID: 27626899, PII: 2553360, DOI: 10.1117/1.JBO.21.9.090503, ISSN: 1560-2281.
Adeniji A, Uddin MJ, Zang T, Tamae D, Wangtrakuldee P, Marnett LJ, Penning TM. Discovery of (R)-2-(6-Methoxynaphthalen-2-yl)butanoic Acid as a Potent and Selective Aldo-keto Reductase 1C3 Inhibitor. J. Med. Chem [print-electronic]. 2016 Aug 8/25/2016; 59(16): 7431-44. PMID: 27486833, DOI: 10.1021/acs.jmedchem.6b00160, ISSN: 1520-4804.
Uddin MJ, Werfel TA, Crews BC, Gupta MK, Kavanaugh TE, Kingsley PJ, Boyd K, Marnett LJ, Duvall CL. Fluorocoxib A loaded nanoparticles enable targeted visualization of cyclooxygenase-2 in inflammation and cancer. Biomaterials [print-electronic]. 2016 Jun; 92: 71-80. PMID: 27043768, PMCID: PMC4833621, PII: S0142-9612(16)30049-7, DOI: 10.1016/j.biomaterials.2016.03.028, ISSN: 1878-5905.
Uddin MI, Evans SM, Craft JR, Capozzi ME, McCollum GW, Yang R, Marnett LJ, Uddin MJ, Jayagopal A, Penn JS. In Vivo Imaging of Retinal Hypoxia in a Model of Oxygen-Induced Retinopathy. Sci Rep. 2016; 6: 31011. PMID: 27491345, PMCID: PMC4974503, PII: srep31011, DOI: 10.1038/srep31011, ISSN: 2045-2322.
Wilson AJ, Fadare O, Beeghly-Fadiel A, Son DS, Liu Q, Zhao S, Saskowski J, Uddin MJ, Daniel C, Crews B, Lehmann BD, Pietenpol JA, Crispens MA, Marnett LJ, Khabele D. Aberrant over-expression of COX-1 intersects multiple pro-tumorigenic pathways in high-grade serous ovarian cancer. Oncotarget. 2015 Aug 8/28/2015; 6(25): 21353-68. PMID: 25972361, PMCID: PMC4673270, PII: 3860, DOI: 10.18632/oncotarget.3860, ISSN: 1949-2553.
Uddin MI, Evans SM, Craft JR, Marnett LJ, Uddin MJ, Jayagopal A. Applications of azo-based probes for imaging retinal hypoxia. ACS Med Chem Lett. 2015 Apr 4/9/2015; 6(4): 445-9. PMID: 25893047, PMCID: PMC4394343, DOI: 10.1021/ml5005206, ISSN: 1948-5875.
Ra H, González-González E, Uddin MJ, King BL, Lee A, Ali-Khan I, Marnett LJ, Tang JY, Contag CH. Detection of non-melanoma skin cancer by in vivo fluorescence imaging with fluorocoxib A. Neoplasia. 2015 Feb; 17(2): 201-7. PMID: 25748239, PMCID: PMC4351298, PII: S1476-5586(14)00199-7, DOI: 10.1016/j.neo.2014.12.009, ISSN: 1476-5586.
Uddin MJ, Elleman AV, Ghebreselasie K, Daniel CK, Crews BC, Nance KD, Huda T, Marnett LJ. Design of Fluorine-Containing 3,4-Diarylfuran-2(5H)-ones as Selective COX-1 Inhibitors. ACS Med Chem Lett. 2014 Nov 11/13/2014; 5(11): 1254-8. PMID: 25408841, PMCID: PMC4233350, DOI: 10.1021/ml500344j, ISSN: 1948-5875.
Perrone MG, Malerba P, Uddin MJ, Vitale P, Panella A, Crews BC, Daniel CK, Ghebreselasie K, Nickels M, Tantawy MN, Manning HC, Marnett LJ, Scilimati A. PET radiotracer [¹8F]-P6 selectively targeting COX-1 as a novel biomarker in ovarian cancer: preliminary investigation. Eur J Med Chem [print-electronic]. 2014 Jun 6/10/2014; 80: 562-8. PMID: 24832612, PMCID: PMC4401082, PII: S0223-5234(14)00403-6, DOI: 10.1016/j.ejmech.2014.04.074, ISSN: 1768-3254.
Uddin MJ, Crews BC, Huda I, Ghebreselasie K, Daniel CK, Marnett LJ. Trifluoromethyl fluorocoxib a detects cyclooxygenase-2 expression in inflammatory tissues and human tumor xenografts. ACS Med Chem Lett. 2014 Apr 4/10/2014; 5(4): 446-50. PMID: 24900856, PMCID: PMC4027729, DOI: 10.1021/ml400485g, ISSN: 1948-5875.
Blobaum AL, Uddin MJ, Felts AS, Crews BC, Rouzer CA, Marnett LJ. The 2'-Trifluoromethyl Analogue of Indomethacin Is a Potent and Selective COX-2 Inhibitor. ACS Med Chem Lett [print-electronic]. 2013 May 5/9/2013; 4(5): 486-90. PMID: 23687559, PMCID: PMC3654564, DOI: 10.1021/ml400066a, ISSN: 1948-5875.
Uddin MJ, Crews BC, Ghebreselasie K, Marnett LJ. Design, synthesis, and structure-activity relationship studies of fluorescent inhibitors of cycloxygenase-2 as targeted optical imaging agents. Bioconjug. Chem [print-electronic]. 2013 Apr 4/17/2013; 24(4): 712-23. PMID: 23488616, PMCID: PMC3630741, DOI: 10.1021/bc300693w, ISSN: 1520-4812.
Uddin MJ, Crews BC, Ghebreselasie K, Huda I, Kingsley PJ, Ansari MS, Tantawy MN, Reese J, Marnett LJ. Fluorinated COX-2 inhibitors as agents in PET imaging of inflammation and cancer. Cancer Prev Res (Phila) [print-electronic]. 2011 Oct; 4(10): 1536-45. PMID: 21900596, PMCID: PMC3214660, PII: 1940-6207.CAPR-11-0120, DOI: 10.1158/1940-6207.CAPR-11-0120, ISSN: 1940-6215.
Uddin MJ, Schulte MI, Maddukuri L, Harp J, Marnett LJ. Semisynthesis of 6-chloropurine-2'-deoxyriboside 5'-dimethoxytrityl 3'-(2-cyanoethyl-N,N-diisopropylamino)phosphoramidite and its use in the synthesis of fluorescently labeled oligonucleotides. Nucleosides Nucleotides Nucleic Acids. 2010 Nov; 29(11): 831-40. PMID: 21128170, PMCID: PMC3019237, PII: 930388354, DOI: 10.1080/15257770.2010.530332, ISSN: 1532-2335.
Uddin MJ, Crews BC, Blobaum AL, Kingsley PJ, Gorden DL, McIntyre JO, Matrisian LM, Subbaramaiah K, Dannenberg AJ, Piston DW, Marnett LJ. Selective visualization of cyclooxygenase-2 in inflammation and cancer by targeted fluorescent imaging agents. Cancer Res. 2010 May 5/1/2010; 70(9): 3618-27. PMID: 20430759, PMCID: PMC2864539, PII: 70/9/3618, DOI: 10.1158/0008-5472.CAN-09-2664, ISSN: 1538-7445.
Uddin MJ, Smithson DC, Brown KM, Crews BC, Connelly M, Zhu F, Marnett LJ, Guy RK. Podophyllotoxin analogues active versus Trypanosoma brucei. Bioorg. Med. Chem. Lett [print-electronic]. 2010 Mar 3/1/2010; 20(5): 1787-91. PMID: 20129783, PMCID: PMC2826502, PII: S0960-894X(10)00011-9, DOI: 10.1016/j.bmcl.2010.01.009, ISSN: 1464-3405.
Konkle ME, Hargrove TY, Kleshchenko YY, von Kries JP, Ridenour W, Uddin MJ, Caprioli RM, Marnett LJ, Nes WD, Villalta F, Waterman MR, Lepesheva GI. Indomethacin amides as a novel molecular scaffold for targeting Trypanosoma cruzi sterol 14alpha-demethylase. J. Med. Chem. 2009 May 5/14/2009; 52(9): 2846-53. PMID: 19354253, PMCID: PMC2744100, DOI: 10.1021/jm801643b, ISSN: 1520-4804.
Uddin, M. J., Crews, B. C., Blobaum, A. L., Kingslay, P. J., Ghebraselase, K., Saleh, S. S., Clanton, J. A., Baldwin, R. M. and Marnett, L. J.. Synthesis and evaluation of [123I]-indomethacin derivatives as COX-2 targeted imaging agents. Journal of Labelled Compounds and Radiopharmaceuticals. 2009; 52: 387-93.
Uddin MJ, Marnett LJ. Synthesis of 5- and 6-carboxy-X-rhodamines. Org. Lett [print-electronic]. 2008 Nov 11/6/2008; 10(21): 4799-801. PMID: 18837556, PMCID: PMC2646678, DOI: 10.1021/ol801904k, ISSN: 1523-7052.
Anning, P. B.; Coles, B; Morton, J.; Wang, H.; Uddin, M. J.; Morrow, J. D.; Dey, S. K.; Marnett, L. J.; Odonnell, V. B.. Nitric oxide deficiency promotes vascular side effects of cyclooxygenase inhibitors. Blood. 2006; 13: 4059.
Uddin MJ, Rao PN, McDonald R, Knaus EE. Design and synthesis of (E)-1,1,2-triarylethenes: novel inhibitors of the cyclooxygenase-2 (COX-2) isozyme. Bioorg. Med. Chem. Lett. 2005 Jan 1/17/2005; 15(2): 439-42. PMID: 15603969, PII: S0960-894X(04)01291-0, DOI: 10.1016/j.bmcl.2004.10.050, ISSN: 0960-894X.
Uddin MJ, Praveen Rao PN, Knaus EE. Design and synthesis of (Z)-1,2-diphenyl-1-(4-methanesulfonamidophenyl)alk-1-enes and (Z)-1-(4-azidophenyl)-1,2-diphenylalk-1-enes: novel inhibitors of cyclooxygenase-2 (COX-2) with anti-inflammatory and analgesic activity. Bioorg. Med. Chem. 2005 Jan 1/17/2005; 13(2): 417-24. PMID: 15598562, PII: S0968-0896(04)00791-6, DOI: 10.1016/j.bmc.2004.10.017, ISSN: 0968-0896.
Uddin MJ, Praveen Rao PN, McDonald R, Knaus EE. A new class of acyclic 2-alkyl-1,1,2-triaryl (Z)-olefins as selective cyclooxygenase-2 inhibitors. J. Med. Chem. 2004 Nov 11/18/2004; 47(24): 6108-11. PMID: 15537365, DOI: 10.1021/jm049523y, ISSN: 0022-2623.
Uddin MJ, Rao PN, Knaus EE. Design and synthesis of acyclic triaryl (Z)-olefins: a novel class of cyclooxygenase-2 (COX-2) inhibitors. Bioorg. Med. Chem. 2004 Nov 11/15/2004; 12(22): 5929-40. PMID: 15498669, PII: S0968-0896(04)00624-8, DOI: 10.1016/j.bmc.2004.08.021, ISSN: 0968-0896.
Uddin MJ, Rao PN, Rahim MA, McDonald R, Knaus EE. A new class of acyclic 2-alkyl-1,2-diaryl (E)-olefins as selective cyclooxygenase-2 (COX-2) inhibitors. Bioorg. Med. Chem. Lett. 2004 Oct 10/4/2004; 14(19): 4911-4. PMID: 15341950, PII: S0960-894X(04)00919-9, DOI: 10.1016/j.bmcl.2004.07.027, ISSN: 0960-894X.
Rao PN, Uddin MJ, Knaus EE. Design, synthesis, and structure-activity relationship studies of 3,4,6-triphenylpyran-2-ones as selective cyclooxygenase-2 inhibitors. J. Med. Chem. 2004 Jul 7/29/2004; 47(16): 3972-90. PMID: 15267236, DOI: 10.1021/jm049939b, ISSN: 0022-2623.
Uddin MJ, Rao PN, Knaus EE. Design of acyclic triaryl olefins: a new class of potent and selective cyclooxygenase-2 (COX-2) inhibitors. Bioorg. Med. Chem. Lett. 2004 Apr 4/19/2004; 14(8): 1953-6. PMID: 15050635, PII: S0960894X04001556, DOI: 10.1016/j.bmcl.2004.01.075, ISSN: 0960-894X.
Uddin, M. J.; Rao, P. N. P.; Knaus, E. E.. Methylsulfonyl and Hydroxyl Substituents Induce (Z)-Stereocontrol in the McMurry Olefination Reaction. Synlett. 2004; 1513.
Uddin MJ, Rao PN, Knaus EE. Design and synthesis of novel celecoxib analogues as selective cyclooxygenase-2 (COX-2) inhibitors: replacement of the sulfonamide pharmacophore by a sulfonylazide bioisostere. Bioorg. Med. Chem. 2003 Nov 11/17/2003; 11(23): 5273-80. PMID: 14604691, PII: S0968089603005583, ISSN: 0968-0896.
Uddin, M. J.; Rao, P. N. P.; Knaus, E. E. Design, Synthesis and Biological Evaluation of Novel Rofecoxib Analogs as Potential Cyclooxygenase-2 (COX-2) Inhibitors: Replacement of Methylsulfonyl Pharmacophore by a Sulfonylazide Bioisostre. Journal of Heterocyclic Chemistry. 2003; 40: 861.
Uddin, M. J.; Kikuchi, M.; Takedatsu, K.; Arai, K.-I.; Fujimoto, T.; Motoyoshiya, J.; Kakehi, A.; Iriue, R.; Shirai, H.; Yamamoto, I.. Synthesis and Structure of Condensed Heterocycles Derived from Intramolecular 1,3-Dipolar Cycloaddition of Transient and Enantiomerically Pure ?-Allylamino Nitrones and Nitrile Oxides in a High Level of Diastereoselectivity. Synthesis. 2000; 365.
Uddin, M. J.; Fujimoto, T.; Kakehi, A.; Shirai, H.; Yamamoto, I.. Diastereoselective Synthesis of Bridgehead Heterocyclic Spiro Compounds Derived from Tandem Michael Intramolecular 1,3-Dipolar Cycloaddition of Nitrones. Heterocyclic Communications. 2000; 6: 113.
Uddin, M. J.; Shinooka, A.; Fujimoto, T.; Shirai, H.; Yamamoto, I.. Isoxazolidine Based New Chral Auxiliary for Asymmetric Synthesis. Heterocyclic Communications. 2000; 6: 505.
Book Chapters:
1. Vision, Sensing and Analytics: Integrative Approaches. Book Details: Date Published June 6, 2021, Volume 207. Page 416. ISBN 978-3-030-75490-7 (eBook). https://doi.org/10.1007/978-3-030-75490-7, © Springer Nature Switzerland AG 2021.
2. Translational Research in Biophotonics Book Details: Date Published May 1, 2014, Volume PM246. Page 362. ISBN: 9781628410686. https://doi.org/10.1117/3.1002515. © SPIE Press, Bellingham, Washington USA.
Selected News Highlights:
1. "Uddin receives second Phi Beta Psi national research award." https://medschool.vanderbilt.edu/basic-sciences/2023/08/24/uddin-receives-a-second-phi-beta-psi-national-research-award-2/
Md. Jashim Uddin, research associate professor of biochemistry, has received the Phi Beta Psi national research award for the second year in a row. The award will fund an ongoing project in which Uddin and colleagues are working to develop an improved cancer imaging platform and technique. There has been significant interest within the field of personalized medicine in developing nanotechnologies capable of diagnosis and drug delivery and that can monitor therapeutic response in real time when treating cancer—an unmet medical need today. Strategies for detecting molecular biomarkers associated with the initiation of cancer can facilitate early detection and timely surgical or therapeutic intervention. The discovery that COX-2 is expressed in colon polyps and colon cancers at higher levels than in normal tissue was recapitulated in solid tumors from many other organs. Mechanistic studies indicate that COX-2-generated prostaglandins regulate multiple tumor phenotypes, including proliferation, resistance to apoptosis, cell motility, and angiogenesis, which makes COX-2 an ideal target for molecular imaging and targeted chemotherapy of carcinogenesis.
Along with Uddin, Distinguished Professor of Chemistry, Biochemistry, and Pharmacology Lawrence Marnett and colleagues carried out proof-of-principle imaging experiments showing that COX-2 is an ideal target for the delivery of targeted imaging probes and cytotoxic agents to tissues containing elevated levels of the enzyme. Now, the second Phi Beta Psi fund has been awarded to Uddin for the development of a nanotechnology in which disease diagnosis and therapy are combined. Today, the call for personalized medicine demands a new nanoplatform for the simultaneous delivery of both imaging and therapeutic agents to preneoplastic or neoplastic tissues for imaging to be performed not only before or after, but also during a treatment procedure. This project is uniquely built for image-guided intervention of colorectal carcinogenesis.
2. "Uddin receives Phi Beta Psi award to continue development of diagnostic tool for detecting pathological cells". https://medschool.vanderbilt.edu/basic-sciences/2022/12/14/uddin-receives-phi-beta-psi-award-to-continue-development-of-diagnostic-tool-for-detecting-pathological-cells/
Md. Jashim Uddin, research associate professor of biochemistry, has received a 2022 National Project Research Grant from Phi Beta Psi. Uddin was one of six recipients nationally and is the first-ever Vanderbilt faculty member to receive this award. The Phi Beta Psi Sorority is a national civic organization whose members are committed to charitable work and fighting against cancer.
Uddin’s funded project* seeks to advance diagnostic efforts, focusing on the use of a nanotechnology-based probe to enable early detection of colorectal cancer. The goal is to employ nanotechnology in the molecular endoscopic visualization of colon cancer, an aim that builds on recent research he published in ACS Chemical Biology. That paper, published this summer, describes a new probe called fluorocoxib Q, or FQ, which Uddin developed along with fellow researchers in the laboratory of Lawrence Marnett, Mary Geddes Stahlman Professor of Cancer Research and University Distinguished Professor of Biochemistry and Chemistry. The new probe that can be used to distinguish pathological or diseased cells from other, healthy cells, was key to getting the Phi Beta Psi award.
COX-2, the enzyme targeted by the probe, is involved in the synthesis of prostaglandins, which facilitate inflammation. Accordingly, COX-2 is overexpressed in inflamed and neoplastic (abnormally growing) tissues while absent in normal tissues. Thanks to its role in pathogenesis, COX-2 is a promising molecular target for detecting pathological cells and strengthening diagnostic imaging.
Previous work suggests that COX-2 activity is associated with the production of reactive oxygen species, or ROS, which in turn increases the oxidation in the environment. Extending earlier work with COX-2-targeted radiological and optical imaging agents, Uddin and Marnett have now developed a “redox-activatable” imaging agent that specifically binds to COX-2 and is only detectable in the presence of ROS. The team of Vanderbilt scientists evaluated the potential of FQ in both cultured cancer cells and a mouse model of inflammation and established that the use of FQ resulted in higher specificity and less background noise when visualizing pathogenesis compared to other agents.
This new probe is the focus of Uddin’s Phi Beta Psi award, which will allow him to evaluate the use of FQ—encapsulated in a variety of nanoparticles—to use endoscopic optical imaging to detect colonic adenomas, a type of pre-cancerous tumor of the colon. Moreover, he will use the funds to verify that FQ fluoresces specifically in the presence of COX-2 and ROS in colorectal carcinogenesis. The development of FQ, as well as Uddin’s planned work with the nanoparticles, will create a framework for using the presence of COX-2 and ROS as biomarkers of neoplasia in the colon and will facilitate the development of the nanotechnology for the early detection, margin delineation, and surgical removal of colorectal cancer in patients.
*Uddin’s grant proposal was supported by Research Development and Support, which offers proposal development assistance for both private (foundations) and federally funded opportunities. Services include searches for new sponsors, coordination and team building for proposals of any size, content development, and draft review. RDS further supports faculty by building relationships with external sponsors, hosting workshops, and providing guides and language for common proposal requirements. RDS is in the Office of the Vice Provost for Research and Innovation. To learn more about RDS or request services, contact them at rds@vanderbilt.edu.
3. "What’s New in Science?" https://medschool.vanderbilt.edu/basic-sciences/2024/03/07/whats-new-in-science/
Detecting adenomas by colonoscopy remains one of the main preventative measures for colorectal cancer, with almost 100,000 adenomas identified during first-time screenings per year in the U.S. Unfortunately, using white-light colonoscopy—the clinical standard—without probing for a particular molecular marker of adenomas can lead to 30% of lesions going undetected. Md. Jashim Uddin, research associate professor of biochemistry, Larry Marnett, Mary Geddes Stahlman Professor of Cancer Research and university distinguished professor of biochemistry, and colleagues chose to use cyclooxygenase-2 or COX-2, an enzyme that increases inflammation and that is upregulated in preneoplastic lesions and colorectal cancer, as the marker to target when developing a fluorescent imaging agent to improve adenoma detection.
This work, reported in the Journal of Biomedical Optics, signifies an advance in adenoma detection by colonoscopy, which could reduce the number of colorectal cancer cases considering that adenomas, precursor lesions, can be removed during colonoscopies. In 2010, the researchers discovered a fluorescent inhibitor of COX-2 called fluorocoxib A; it was the first COX-2-targeted molecular imaging agent for the in vivo fluorescence imaging of inflammation and cancer and has since been widely used in research in the U.S. and across the globe. Now, the authors sought to forge a path to the clinic and packaged fluorocoxib A into an FDA-approved polymer to improve delivery to the adenomas. Uddin and colleagues administered fluorocoxib A to mice before a colonoscopy, which allowed them to clearly identify colonic adenomas in mice containing elevated levels of COX-2 in the lesions. The colon tissues of normal mice were not illuminated with the fluorescent compound, indicative of the lack of lesions. Pre-dosing the mice with a non-fluorescent inhibitor of COX-2 or with a fluorescent molecule that does not inhibit COX-2 led to minimal labeling of adenomas. Packaging the COX-2 inhibitor in the FDA-approved polymer creates a tractable path for clinical trials that could ultimately impact adenoma detection for the millions who undergo colonoscopies every year across the country. Uddin, M.J., Niitsu, H., Coffey, R.J., Marnett, L.J. (2023). Development of Pluoronic nanoparticles of fluorocoxib A for endoscopic fluorescence imaging of colonic adenomas. J Biomed Opt. 2023;28(4):040501.
4. "Potential probe for early ovarian cancer." https://news.vumc.org/2019/06/20/imaging-probe-ovarian-cancer/
Ovarian cancer is the fifth leading cause of cancer death in women and one of the most difficult malignancies to detect at an early stage. Emerging clinical evidence suggests that the enzyme cyclooxygenase-1 (COX-1) contributes significantly to tumorigenesis in ovarian cancer. Thus COX-1 could serve as a novel target for molecular imaging probes to improve early detection and response to treatment. Now in the American Chemical Society journal ACS Omega, Md. Jashim Uddin, PhD, Lawrence Marnett, PhD, and colleagues report the discovery of FDF, a furanone-based novel COX-1 selective inhibitor with adequate properties to enable its use for in vivo imaging. In two distinct animal models of ovarian cancer, xenografts expressing high levels of COX-1 demonstrated targeted uptake of the compound containing the F-18 radioisotope (18F-FDF) compared to tissues expressing low protein levels. This indicates that 18F-FDF may be the first feasible radiotracer validated for targeted PET/CT imaging of neoplastic tissues that express elevated levels of the COX-1 enzyme. The work was featured in the journal as an ACS Editors’ Choice and was supported by grants from the National Institutes of Health (CA128323, CA182850, CA136465, CA089450) and Kay Yow Cancer Fund/V Foundation.
5. "Fluorescent compounds make tumors glow." https://www.sciencedaily.com/releases/2010/04/100429082357.htm
6. "Jashim Uddin has received the prestigious Phi Beta Psi national research award." https://en.ittefaq.com.bd/6159/uddin-receives-a-second-phi-beta-psi-national
7. "Better adenoma detection." https://www.nashvillemedicalnews.com/article/6020/better-adenoma-detection
8. "Challenge puts technology transfer ingenuity on display." https://lab.vanderbilt.edu/jashim-uddin/wp-content/uploads/sites/105/2021/06/%E2%80%98Challenge%E2%80%99-puts-technology-transfer-ingenuity-on-display-VUMC-Reporter-Vanderbilt-University.pdf
9. "Detecting Ovarian cancer earlier." https://cdn.vanderbilt.edu/vu-web/lab-wpcontent/sites/105/2021/05/03213331/1-Discover-Jul312019.pdf
10. "Diagnosing and differentiating cancer at the molecular level." https://cdn.vanderbilt.edu/vu-web/lab-wpcontent/sites/105/2021/05/04152753/CTScan-Nov72011.pdf
Contact:
615-484-8674
jashim.uddin@vanderbilt.edu
https://wag.app.vanderbilt.edu/PublicPage/Faculty/Details/33074
Jashim's research interests include development of targeted imaging agents for early detection for cancer and discovery of chemotherapeutic medicines for effective treatment of neoplastic diseases.
Major Accomplishments:
1. Discovery of Fluorocoxib Q, the 1st redox-activatable COX-2 inhibitor in 2022.
2. Discovery of Chemocoxib A, the 1st cytotoxic COX-2 inhibitor, 2016.
3. Discovery of Fluorocoxib A (Trade Mark: XenoLight), the 1st COX-2 targeted optical imaging agent, licensed to Perkin Elmar Pharma in 2014.
National Awards/Grants:
1. Phi Beta Psi Trust, National Research Award, AWD00001248 (Role: Principal Investigator/Program Director) 08/01/2023-08/15/2025, $140K.
2. National Institutes of Health (NIH), National Research Award, R01 CA260958-01A1 (Role: Multiple Principal Investigator/Program Director) 7/05/2021–06/30/2026, $3M.
Fellowships/Recognitions:
1. Recipient of the Financial Incentives Award from the Vanderbilt University School of Medicine Basic Sciences for securing two nationally competitive research grants.
Inclusive Date: 07/14/2023.
2. Recipient of OMICS Certificate of Recognition for research excellence in molecular imaging of COX-2 in cancer and inflammation at the International Conference on Radiology and Imaging in Chicago-North Shore.
Inclusive Date: 08/14/2013.
3. Recipient of Alberta Heritage Foundation for Medical Research (AHFMR) Post-doctoral Fellowship Award.
Inclusive Dates: 01/01/2002 – 12/31/2004.
4. Recipient of the Japanese Government (MONBUSHO) Graduate Scholarship Award, Department of Education, Japan.
Inclusive Dates: 09/02/1997 – 03/31/2001.
Professional Activities:
1. Ad Hoc Grant Reviewer, National Cancer Institute. Imaging Probe & Contrast Agents (IPCA) Study Section.
Inclusive Date: 02/2022 - Present
2. Ad Hoc Grant Reviewer, North Carolina Biotech Center Interdisciplinary Grant Program.
Inclusive Date: 03/2005 - Present
3. Chairman, Executive Committee, Network for Translational Research (NTR) Chemistry Core, National Institutes of Health.
Inclusive Dates: 02/2012 - 01/2013.
4. Member, Executive Committee, American Association of Cancer Research-American Chemical Society-Joint Meeting on Chemistry in Cancer Research, San Diego.
Inclusive Date: 01/2011 - 01/2012.
Patents:
1. Compounds and methods for imaging cancer (US0280543 A1 2018, US 10,792,377 B2 2020). Disclosed materials are diagnostic agents comprised of a radical and a fluorophore moiety. Disclosed technology methods for developing smart probes enable visualization of cells associated with cancer, inflammation, or disorders associated with carcinogenesis.
2. Composition and method for detecting hypoxia (US 179117 A1 2016, US10,695,446 B2 2020). Disclosed subject matter comprised diagnostic agent conjugated to a hypoxia marker moiety. Disclosed methods and compositions for diagnosing (i.e., by optical imaging) hypoxic cells and/or treating a disorder associated with hypoxia.
3. Fluorocoxib A loading into ROS-responsive nanoparticles (US0007723 A1 2017, US 10,105,455 B2 2018). Disclosed are compositions and methods for making and using the disclosed compositions. In a further aspect, disclosed are compositions that comprise a cyclooxygenase-2-selective therapeutic and/or diagnostic agent having a therapeutic and/or diagnostic agent conjugated to a NSAID drug; and a ROS-responsive nanoparticle.
4. Methods and compositions for diagnostic and therapeutic targeting of COX-2 (US 0254910 A1 2010, WO149456 A2 2007, WO149456 A3 2007, US 8,865,130 B2 2014). Disclosed subject matter provides compositions that selectively bind cyclooxygenase-2 and comprise a therapeutic and/or diagnostic moiety. Also, provided are methods for using the disclosed compositions for diagnosing (i.e. by imaging) a target cell and/or treating a disorder associated with a cyclooxygenase-2 biological activities.
Publications:
Asaduzzaman A, Thompson CC, Uddin MJ. Machine Learning Approaches for Skin Neoplasm Diagnosis. ACS Omega. 2024 Jul 7/8/2024; DOI: 10.1021/acsomega.4c03640.
Uddin MJ, et al. Polymeric Micellar Nanoparticles Enable Image-guided Drug Delivery in Solid Tumors. BioRxiv. 2024 Jun 6/7/2024; DOI: 10.1101/2024.06.07.598019.
Asaduzzaman A, Thompson CC, Uddin MJ. Machine Learning Approaches for Skin Neoplasm Diagnosis. BioRxiv. 2024 May 5/12/2024; DOI: 10.1101/2024.05.12.593773.
Uddin MJ, Niitsu H, Coffey RJ, Marnett LJ. Development of Pluoronic nanoparticles of fluorocoxib A for endoscopic fluorescence imaging of colonic adenomas [letter]. J Biomed Opt [print-electronic]. 2023 Apr; 28(4): 40501. PMID: 37091910, PMCID: PMC10118138, PII: 220308LR, DOI: 10.1117/1.JBO.28.4.040501, ISSN: 1560-2281.
Aleem AM, Kang W, Lin S, Milad M, Kingsley PJ, Crews BC, Uddin MJ, Rouzer CA, Marnett LJ. Ferroptosis Inhibitors Suppress Prostaglandin Synthesis in Lipopolysaccharide-Stimulated Macrophages. ACS Chem Biol [print-electronic]. 2023 Jan 1/13/2023; PMID: 36638351, DOI: 10.1021/acschembio.2c00869, ISSN: 1554-8937.
Uddin MJ, Lo JH, Oltman CG, Crews BC, Huda T, Liu J, Kingsley PJ, Lin S, Milad M, Aleem AM, Asaduzzaman A, McIntyre JO, Duvall CL, Marnett LJ. Discovery of a Redox-Activatable Chemical Probe for Detection of Cyclooxygenase-2 in Cells and Animals. ACS Chem Biol [print-electronic]. 2022 Jul 7/15/2022; 17(7): 1714-22. PMID: 35786843, DOI: 10.1021/acschembio.1c00961, ISSN: 1554-8937.
Winters ND, Bedse G, Astafyev AA, Patrick TA, Altemus M, Morgan AJ, Mukerjee S, Johnson KD, Mahajan VR, Uddin MJ, Kingsley PJ, Centanni SW, Siciliano CA, Samuels DC, Marnett LJ, Winder DG, Patel S. Targeting diacylglycerol lipase reduces alcohol consumption in preclinical models. J Clin Invest [print-electronic]. 2021 Jul 7/22/2021; 131(17): PMID: 34292886, PMCID: PMC8409586, PII: e146861, DOI: 10.1172/JCI146861, ISSN: 1558-8238.
Malerba P, Crews BC, Ghebreselasie K, Daniel CK, Jashim E, Aleem AM, Salam RA, Marnett LJ, Uddin MJ. Targeted Detection of Cyclooxygenase-1 in Ovarian Cancer. ACS Med Chem Lett. 2020 Oct 10/8/2020; 11(10): 1837-42. PMID: 33062161, PMCID: PMC7549111, DOI: 10.1021/acsmedchemlett.9b00280, ISSN: 1948-5875.
Uddin MJ, Xu S, Crews BC, Aleem AM, Ghebreselasie K, Banerjee S, Marnett LJ. Harmaline Analogs as Substrate-Selective Cyclooxygenase-2 Inhibitors. ACS Med Chem Lett. 2020 Oct 10/8/2020; 11(10): 1881-5. PMID: 33062168, PMCID: PMC7549255, DOI: 10.1021/acsmedchemlett.9b00555, ISSN: 1948-5875.
Uddin MJ, Vemulapalli A, Niitsu H, Crews BC, Oltman CG, Kingsley PJ, Kavanaugh TE, Bedingfield SK, Mcintyre JO, Milad M, Aleem AM, Coffey RJ, Duvall CL, Marnett LJ. Molecular Imaging of Inflammation in Osteoarthritis Using a Water-Soluble Fluorocoxib. ACS Med Chem Lett. 2020 Oct 10/8/2020; 11(10): 1875-80. PMID: 33062167, PMCID: PMC7549260, DOI: 10.1021/acsmedchemlett.9b00512, ISSN: 1948-5875.
Cekanova M, Pandey S, Olin S, Ryan P, Stokes JE, Hecht S, Martin-Jimenez T, Uddin MJ, Marnett LJ. Pharmacokinetic characterization of fluorocoxib D, a cyclooxygenase-2-targeted optical imaging agent for detection of cancer. J Biomed Opt. 2020 Aug; 25(8): PMID: 32860356, PMCID: PMC7456637, PII: JBO-200044R, DOI: 10.1117/1.JBO.25.8.086005, ISSN: 1560-2281.
Bourn J, Rathore K, Donnell R, White W, Uddin MJ, Marnett L, Cekanova M. Detection of carcinogen-induced bladder cancer by fluorocoxib A. BMC Cancer. 2019 Nov 11/27/2019; 19(1): 1152. PMID: 31775672, PMCID: PMC6882158, PII: 10.1186/s12885-019-6366-x, DOI: 10.1186/s12885-019-6366-x, ISSN: 1471-2407.
Uddin MJ, Wilson AJ, Crews BC, Malerba P, Uddin MI, Kingsley PJ, Ghebreselasie K, Daniel CK, Nickels ML, Tantawy MN, Jashim E, Manning HC, Khabele D, Marnett LJ. Discovery of Furanone-Based Radiopharmaceuticals for Diagnostic Targeting of COX-1 in Ovarian Cancer. ACS Omega [print-electronic]. 2019 May 5/31/2019; 4(5): 9251-61. PMID: 31172046, PMCID: PMC6545551, DOI: 10.1021/acsomega.9b01093, ISSN: 2470-1343.
Xu S, Uddin MJ, Banerjee S, Duggan K, Musee J, Kiefer JR, Ghebreselasie K, Rouzer CA, Marnett LJ. Conjugated Indomethacin Fluorescent Inhibitors Utilize the Membrane Binding Domain of Cyclooxygenase-2 to Accommodate the Tethered Moiety. J. Biol. Chem. 2019 Apr 4/30/2019; 294(22): 8690-8. PMID: 31000626.
Bourn J, Pandey S, Uddin MJ, Marnett LJ, Cekanova M. Detection of tyrosine kinase inhibitors-induced COX-2 expression in bladder cancer by fluorocoxib A. Oncotarget. 2019 Jan 1/29/2019; 10(48).
Shaheen SM, Azad AK, Rahman MM, Uddin MJ. A comparative transgene expression study between a protaplex and a rotaplex embedded lipid-nanoparticles in murine derived dendritic cell. J Interdiscipl Nanomed. 2018 Jul 7/10/2018; 0(0).
Cavener VS, Gaulden A, Pennipede D, Jagasia P, Uddin J, Marnett LJ, Patel S. Inhibition of Diacylglycerol Lipase Impairs Fear Extinction in Mice. Front Neurosci. 2018; 12: 479. PMID: 30108473, PMCID: PMC6080414, DOI: 10.3389/fnins.2018.00479, ISSN: 1662-4548.
Bedse G, Hartley ND, Neale E, Gaulden AD, Patrick TA, Kingsley PJ, Uddin MJ, Plath N, Marnett LJ, Patel S. Functional Redundancy Between Canonical Endocannabinoid Signaling Systems in the Modulation of Anxiety. Biol. Psychiatry [print-electronic]. 2017 Oct 10/1/2017; 82(7): 488-99. PMID: 28438413, PMCID: PMC5585044, PII: S0006-3223(17)31357-4, DOI: 10.1016/j.biopsych.2017.03.002, ISSN: 1873-2402.
Bluett RJ, Báldi R, Haymer A, Gaulden AD, Hartley ND, Parrish WP, Baechle J, Marcus DJ, Mardam-Bey R, Shonesy BC, Uddin MJ, Marnett LJ, Mackie K, Colbran RJ, Winder DG, Patel S. Endocannabinoid signalling modulates susceptibility to traumatic stress exposure. Nat Commun. 2017 Mar 3/28/2017; 8: 14782. PMID: 28348378, PMCID: PMC5379055, PII: ncomms14782, DOI: 10.1038/ncomms14782, ISSN: 2041-1723.
Foster DJ, Wilson JM, Remke DH, Mahmood MS, Uddin MJ, Wess J, Patel S, Marnett LJ, Niswender CM, Jones CK, Xiang Z, Lindsley CW, Rook JM, Conn PJ. Antipsychotic-like Effects of M4 Positive Allosteric Modulators Are Mediated by CB2 Receptor-Dependent Inhibition of Dopamine Release. Neuron [print-electronic]. 2016 Sep 9/21/2016; 91(6): 1244-52. PMID: 27618677, PII: S0896-6273(16)30509-8, DOI: 10.1016/j.neuron.2016.08.017, ISSN: 1097-4199.
Uddin MJ, Crews BC, Xu S, Ghebreselasie K, Daniel CK, Kingsley PJ, Banerjee S, Marnett LJ. Antitumor Activity of Cytotoxic Cyclooxygenase-2 Inhibitors. ACS Chem. Biol [print-electronic]. 2016 Sep 9/19/2016; PMID: 27588346, DOI: 10.1021/acschembio.6b00560, ISSN: 1554-8937.
Uddin MJ, Moore CE, Crews BC, Daniel CK, Ghebreselasie K, McIntyre JO, Marnett LJ, Jayagopal A. Fluorocoxib A enables targeted detection of cyclooxygenase-2 in laser-induced choroidal neovascularization. J Biomed Opt. 2016 Sep 9/1/2016; 21(9): 90503. PMID: 27626899, PII: 2553360, DOI: 10.1117/1.JBO.21.9.090503, ISSN: 1560-2281.
Adeniji A, Uddin MJ, Zang T, Tamae D, Wangtrakuldee P, Marnett LJ, Penning TM. Discovery of (R)-2-(6-Methoxynaphthalen-2-yl)butanoic Acid as a Potent and Selective Aldo-keto Reductase 1C3 Inhibitor. J. Med. Chem [print-electronic]. 2016 Aug 8/25/2016; 59(16): 7431-44. PMID: 27486833, DOI: 10.1021/acs.jmedchem.6b00160, ISSN: 1520-4804.
Uddin MJ, Werfel TA, Crews BC, Gupta MK, Kavanaugh TE, Kingsley PJ, Boyd K, Marnett LJ, Duvall CL. Fluorocoxib A loaded nanoparticles enable targeted visualization of cyclooxygenase-2 in inflammation and cancer. Biomaterials [print-electronic]. 2016 Jun; 92: 71-80. PMID: 27043768, PMCID: PMC4833621, PII: S0142-9612(16)30049-7, DOI: 10.1016/j.biomaterials.2016.03.028, ISSN: 1878-5905.
Uddin MI, Evans SM, Craft JR, Capozzi ME, McCollum GW, Yang R, Marnett LJ, Uddin MJ, Jayagopal A, Penn JS. In Vivo Imaging of Retinal Hypoxia in a Model of Oxygen-Induced Retinopathy. Sci Rep. 2016; 6: 31011. PMID: 27491345, PMCID: PMC4974503, PII: srep31011, DOI: 10.1038/srep31011, ISSN: 2045-2322.
Wilson AJ, Fadare O, Beeghly-Fadiel A, Son DS, Liu Q, Zhao S, Saskowski J, Uddin MJ, Daniel C, Crews B, Lehmann BD, Pietenpol JA, Crispens MA, Marnett LJ, Khabele D. Aberrant over-expression of COX-1 intersects multiple pro-tumorigenic pathways in high-grade serous ovarian cancer. Oncotarget. 2015 Aug 8/28/2015; 6(25): 21353-68. PMID: 25972361, PMCID: PMC4673270, PII: 3860, DOI: 10.18632/oncotarget.3860, ISSN: 1949-2553.
Uddin MI, Evans SM, Craft JR, Marnett LJ, Uddin MJ, Jayagopal A. Applications of azo-based probes for imaging retinal hypoxia. ACS Med Chem Lett. 2015 Apr 4/9/2015; 6(4): 445-9. PMID: 25893047, PMCID: PMC4394343, DOI: 10.1021/ml5005206, ISSN: 1948-5875.
Ra H, González-González E, Uddin MJ, King BL, Lee A, Ali-Khan I, Marnett LJ, Tang JY, Contag CH. Detection of non-melanoma skin cancer by in vivo fluorescence imaging with fluorocoxib A. Neoplasia. 2015 Feb; 17(2): 201-7. PMID: 25748239, PMCID: PMC4351298, PII: S1476-5586(14)00199-7, DOI: 10.1016/j.neo.2014.12.009, ISSN: 1476-5586.
Uddin MJ, Elleman AV, Ghebreselasie K, Daniel CK, Crews BC, Nance KD, Huda T, Marnett LJ. Design of Fluorine-Containing 3,4-Diarylfuran-2(5H)-ones as Selective COX-1 Inhibitors. ACS Med Chem Lett. 2014 Nov 11/13/2014; 5(11): 1254-8. PMID: 25408841, PMCID: PMC4233350, DOI: 10.1021/ml500344j, ISSN: 1948-5875.
Perrone MG, Malerba P, Uddin MJ, Vitale P, Panella A, Crews BC, Daniel CK, Ghebreselasie K, Nickels M, Tantawy MN, Manning HC, Marnett LJ, Scilimati A. PET radiotracer [¹8F]-P6 selectively targeting COX-1 as a novel biomarker in ovarian cancer: preliminary investigation. Eur J Med Chem [print-electronic]. 2014 Jun 6/10/2014; 80: 562-8. PMID: 24832612, PMCID: PMC4401082, PII: S0223-5234(14)00403-6, DOI: 10.1016/j.ejmech.2014.04.074, ISSN: 1768-3254.
Uddin MJ, Crews BC, Huda I, Ghebreselasie K, Daniel CK, Marnett LJ. Trifluoromethyl fluorocoxib a detects cyclooxygenase-2 expression in inflammatory tissues and human tumor xenografts. ACS Med Chem Lett. 2014 Apr 4/10/2014; 5(4): 446-50. PMID: 24900856, PMCID: PMC4027729, DOI: 10.1021/ml400485g, ISSN: 1948-5875.
Blobaum AL, Uddin MJ, Felts AS, Crews BC, Rouzer CA, Marnett LJ. The 2'-Trifluoromethyl Analogue of Indomethacin Is a Potent and Selective COX-2 Inhibitor. ACS Med Chem Lett [print-electronic]. 2013 May 5/9/2013; 4(5): 486-90. PMID: 23687559, PMCID: PMC3654564, DOI: 10.1021/ml400066a, ISSN: 1948-5875.
Uddin MJ, Crews BC, Ghebreselasie K, Marnett LJ. Design, synthesis, and structure-activity relationship studies of fluorescent inhibitors of cycloxygenase-2 as targeted optical imaging agents. Bioconjug. Chem [print-electronic]. 2013 Apr 4/17/2013; 24(4): 712-23. PMID: 23488616, PMCID: PMC3630741, DOI: 10.1021/bc300693w, ISSN: 1520-4812.
Uddin MJ, Crews BC, Ghebreselasie K, Huda I, Kingsley PJ, Ansari MS, Tantawy MN, Reese J, Marnett LJ. Fluorinated COX-2 inhibitors as agents in PET imaging of inflammation and cancer. Cancer Prev Res (Phila) [print-electronic]. 2011 Oct; 4(10): 1536-45. PMID: 21900596, PMCID: PMC3214660, PII: 1940-6207.CAPR-11-0120, DOI: 10.1158/1940-6207.CAPR-11-0120, ISSN: 1940-6215.
Uddin MJ, Schulte MI, Maddukuri L, Harp J, Marnett LJ. Semisynthesis of 6-chloropurine-2'-deoxyriboside 5'-dimethoxytrityl 3'-(2-cyanoethyl-N,N-diisopropylamino)phosphoramidite and its use in the synthesis of fluorescently labeled oligonucleotides. Nucleosides Nucleotides Nucleic Acids. 2010 Nov; 29(11): 831-40. PMID: 21128170, PMCID: PMC3019237, PII: 930388354, DOI: 10.1080/15257770.2010.530332, ISSN: 1532-2335.
Uddin MJ, Crews BC, Blobaum AL, Kingsley PJ, Gorden DL, McIntyre JO, Matrisian LM, Subbaramaiah K, Dannenberg AJ, Piston DW, Marnett LJ. Selective visualization of cyclooxygenase-2 in inflammation and cancer by targeted fluorescent imaging agents. Cancer Res. 2010 May 5/1/2010; 70(9): 3618-27. PMID: 20430759, PMCID: PMC2864539, PII: 70/9/3618, DOI: 10.1158/0008-5472.CAN-09-2664, ISSN: 1538-7445.
Uddin MJ, Smithson DC, Brown KM, Crews BC, Connelly M, Zhu F, Marnett LJ, Guy RK. Podophyllotoxin analogues active versus Trypanosoma brucei. Bioorg. Med. Chem. Lett [print-electronic]. 2010 Mar 3/1/2010; 20(5): 1787-91. PMID: 20129783, PMCID: PMC2826502, PII: S0960-894X(10)00011-9, DOI: 10.1016/j.bmcl.2010.01.009, ISSN: 1464-3405.
Konkle ME, Hargrove TY, Kleshchenko YY, von Kries JP, Ridenour W, Uddin MJ, Caprioli RM, Marnett LJ, Nes WD, Villalta F, Waterman MR, Lepesheva GI. Indomethacin amides as a novel molecular scaffold for targeting Trypanosoma cruzi sterol 14alpha-demethylase. J. Med. Chem. 2009 May 5/14/2009; 52(9): 2846-53. PMID: 19354253, PMCID: PMC2744100, DOI: 10.1021/jm801643b, ISSN: 1520-4804.
Uddin, M. J., Crews, B. C., Blobaum, A. L., Kingslay, P. J., Ghebraselase, K., Saleh, S. S., Clanton, J. A., Baldwin, R. M. and Marnett, L. J.. Synthesis and evaluation of [123I]-indomethacin derivatives as COX-2 targeted imaging agents. Journal of Labelled Compounds and Radiopharmaceuticals. 2009; 52: 387-93.
Uddin MJ, Marnett LJ. Synthesis of 5- and 6-carboxy-X-rhodamines. Org. Lett [print-electronic]. 2008 Nov 11/6/2008; 10(21): 4799-801. PMID: 18837556, PMCID: PMC2646678, DOI: 10.1021/ol801904k, ISSN: 1523-7052.
Anning, P. B.; Coles, B; Morton, J.; Wang, H.; Uddin, M. J.; Morrow, J. D.; Dey, S. K.; Marnett, L. J.; Odonnell, V. B.. Nitric oxide deficiency promotes vascular side effects of cyclooxygenase inhibitors. Blood. 2006; 13: 4059.
Uddin MJ, Rao PN, McDonald R, Knaus EE. Design and synthesis of (E)-1,1,2-triarylethenes: novel inhibitors of the cyclooxygenase-2 (COX-2) isozyme. Bioorg. Med. Chem. Lett. 2005 Jan 1/17/2005; 15(2): 439-42. PMID: 15603969, PII: S0960-894X(04)01291-0, DOI: 10.1016/j.bmcl.2004.10.050, ISSN: 0960-894X.
Uddin MJ, Praveen Rao PN, Knaus EE. Design and synthesis of (Z)-1,2-diphenyl-1-(4-methanesulfonamidophenyl)alk-1-enes and (Z)-1-(4-azidophenyl)-1,2-diphenylalk-1-enes: novel inhibitors of cyclooxygenase-2 (COX-2) with anti-inflammatory and analgesic activity. Bioorg. Med. Chem. 2005 Jan 1/17/2005; 13(2): 417-24. PMID: 15598562, PII: S0968-0896(04)00791-6, DOI: 10.1016/j.bmc.2004.10.017, ISSN: 0968-0896.
Uddin MJ, Praveen Rao PN, McDonald R, Knaus EE. A new class of acyclic 2-alkyl-1,1,2-triaryl (Z)-olefins as selective cyclooxygenase-2 inhibitors. J. Med. Chem. 2004 Nov 11/18/2004; 47(24): 6108-11. PMID: 15537365, DOI: 10.1021/jm049523y, ISSN: 0022-2623.
Uddin MJ, Rao PN, Knaus EE. Design and synthesis of acyclic triaryl (Z)-olefins: a novel class of cyclooxygenase-2 (COX-2) inhibitors. Bioorg. Med. Chem. 2004 Nov 11/15/2004; 12(22): 5929-40. PMID: 15498669, PII: S0968-0896(04)00624-8, DOI: 10.1016/j.bmc.2004.08.021, ISSN: 0968-0896.
Uddin MJ, Rao PN, Rahim MA, McDonald R, Knaus EE. A new class of acyclic 2-alkyl-1,2-diaryl (E)-olefins as selective cyclooxygenase-2 (COX-2) inhibitors. Bioorg. Med. Chem. Lett. 2004 Oct 10/4/2004; 14(19): 4911-4. PMID: 15341950, PII: S0960-894X(04)00919-9, DOI: 10.1016/j.bmcl.2004.07.027, ISSN: 0960-894X.
Rao PN, Uddin MJ, Knaus EE. Design, synthesis, and structure-activity relationship studies of 3,4,6-triphenylpyran-2-ones as selective cyclooxygenase-2 inhibitors. J. Med. Chem. 2004 Jul 7/29/2004; 47(16): 3972-90. PMID: 15267236, DOI: 10.1021/jm049939b, ISSN: 0022-2623.
Uddin MJ, Rao PN, Knaus EE. Design of acyclic triaryl olefins: a new class of potent and selective cyclooxygenase-2 (COX-2) inhibitors. Bioorg. Med. Chem. Lett. 2004 Apr 4/19/2004; 14(8): 1953-6. PMID: 15050635, PII: S0960894X04001556, DOI: 10.1016/j.bmcl.2004.01.075, ISSN: 0960-894X.
Uddin, M. J.; Rao, P. N. P.; Knaus, E. E.. Methylsulfonyl and Hydroxyl Substituents Induce (Z)-Stereocontrol in the McMurry Olefination Reaction. Synlett. 2004; 1513.
Uddin MJ, Rao PN, Knaus EE. Design and synthesis of novel celecoxib analogues as selective cyclooxygenase-2 (COX-2) inhibitors: replacement of the sulfonamide pharmacophore by a sulfonylazide bioisostere. Bioorg. Med. Chem. 2003 Nov 11/17/2003; 11(23): 5273-80. PMID: 14604691, PII: S0968089603005583, ISSN: 0968-0896.
Uddin, M. J.; Rao, P. N. P.; Knaus, E. E. Design, Synthesis and Biological Evaluation of Novel Rofecoxib Analogs as Potential Cyclooxygenase-2 (COX-2) Inhibitors: Replacement of Methylsulfonyl Pharmacophore by a Sulfonylazide Bioisostre. Journal of Heterocyclic Chemistry. 2003; 40: 861.
Uddin, M. J.; Kikuchi, M.; Takedatsu, K.; Arai, K.-I.; Fujimoto, T.; Motoyoshiya, J.; Kakehi, A.; Iriue, R.; Shirai, H.; Yamamoto, I.. Synthesis and Structure of Condensed Heterocycles Derived from Intramolecular 1,3-Dipolar Cycloaddition of Transient and Enantiomerically Pure ?-Allylamino Nitrones and Nitrile Oxides in a High Level of Diastereoselectivity. Synthesis. 2000; 365.
Uddin, M. J.; Fujimoto, T.; Kakehi, A.; Shirai, H.; Yamamoto, I.. Diastereoselective Synthesis of Bridgehead Heterocyclic Spiro Compounds Derived from Tandem Michael Intramolecular 1,3-Dipolar Cycloaddition of Nitrones. Heterocyclic Communications. 2000; 6: 113.
Uddin, M. J.; Shinooka, A.; Fujimoto, T.; Shirai, H.; Yamamoto, I.. Isoxazolidine Based New Chral Auxiliary for Asymmetric Synthesis. Heterocyclic Communications. 2000; 6: 505.
Book Chapters:
1. Vision, Sensing and Analytics: Integrative Approaches. Book Details: Date Published June 6, 2021, Volume 207. Page 416. ISBN 978-3-030-75490-7 (eBook). https://doi.org/10.1007/978-3-030-75490-7, © Springer Nature Switzerland AG 2021.
2. Translational Research in Biophotonics Book Details: Date Published May 1, 2014, Volume PM246. Page 362. ISBN: 9781628410686. https://doi.org/10.1117/3.1002515. © SPIE Press, Bellingham, Washington USA.
Selected News Highlights:
1. "Uddin receives second Phi Beta Psi national research award." https://medschool.vanderbilt.edu/basic-sciences/2023/08/24/uddin-receives-a-second-phi-beta-psi-national-research-award-2/
Md. Jashim Uddin, research associate professor of biochemistry, has received the Phi Beta Psi national research award for the second year in a row. The award will fund an ongoing project in which Uddin and colleagues are working to develop an improved cancer imaging platform and technique. There has been significant interest within the field of personalized medicine in developing nanotechnologies capable of diagnosis and drug delivery and that can monitor therapeutic response in real time when treating cancer—an unmet medical need today. Strategies for detecting molecular biomarkers associated with the initiation of cancer can facilitate early detection and timely surgical or therapeutic intervention. The discovery that COX-2 is expressed in colon polyps and colon cancers at higher levels than in normal tissue was recapitulated in solid tumors from many other organs. Mechanistic studies indicate that COX-2-generated prostaglandins regulate multiple tumor phenotypes, including proliferation, resistance to apoptosis, cell motility, and angiogenesis, which makes COX-2 an ideal target for molecular imaging and targeted chemotherapy of carcinogenesis.
Along with Uddin, Distinguished Professor of Chemistry, Biochemistry, and Pharmacology Lawrence Marnett and colleagues carried out proof-of-principle imaging experiments showing that COX-2 is an ideal target for the delivery of targeted imaging probes and cytotoxic agents to tissues containing elevated levels of the enzyme. Now, the second Phi Beta Psi fund has been awarded to Uddin for the development of a nanotechnology in which disease diagnosis and therapy are combined. Today, the call for personalized medicine demands a new nanoplatform for the simultaneous delivery of both imaging and therapeutic agents to preneoplastic or neoplastic tissues for imaging to be performed not only before or after, but also during a treatment procedure. This project is uniquely built for image-guided intervention of colorectal carcinogenesis.
2. "Uddin receives Phi Beta Psi award to continue development of diagnostic tool for detecting pathological cells". https://medschool.vanderbilt.edu/basic-sciences/2022/12/14/uddin-receives-phi-beta-psi-award-to-continue-development-of-diagnostic-tool-for-detecting-pathological-cells/
Md. Jashim Uddin, research associate professor of biochemistry, has received a 2022 National Project Research Grant from Phi Beta Psi. Uddin was one of six recipients nationally and is the first-ever Vanderbilt faculty member to receive this award. The Phi Beta Psi Sorority is a national civic organization whose members are committed to charitable work and fighting against cancer.
Uddin’s funded project* seeks to advance diagnostic efforts, focusing on the use of a nanotechnology-based probe to enable early detection of colorectal cancer. The goal is to employ nanotechnology in the molecular endoscopic visualization of colon cancer, an aim that builds on recent research he published in ACS Chemical Biology. That paper, published this summer, describes a new probe called fluorocoxib Q, or FQ, which Uddin developed along with fellow researchers in the laboratory of Lawrence Marnett, Mary Geddes Stahlman Professor of Cancer Research and University Distinguished Professor of Biochemistry and Chemistry. The new probe that can be used to distinguish pathological or diseased cells from other, healthy cells, was key to getting the Phi Beta Psi award.
COX-2, the enzyme targeted by the probe, is involved in the synthesis of prostaglandins, which facilitate inflammation. Accordingly, COX-2 is overexpressed in inflamed and neoplastic (abnormally growing) tissues while absent in normal tissues. Thanks to its role in pathogenesis, COX-2 is a promising molecular target for detecting pathological cells and strengthening diagnostic imaging.
Previous work suggests that COX-2 activity is associated with the production of reactive oxygen species, or ROS, which in turn increases the oxidation in the environment. Extending earlier work with COX-2-targeted radiological and optical imaging agents, Uddin and Marnett have now developed a “redox-activatable” imaging agent that specifically binds to COX-2 and is only detectable in the presence of ROS. The team of Vanderbilt scientists evaluated the potential of FQ in both cultured cancer cells and a mouse model of inflammation and established that the use of FQ resulted in higher specificity and less background noise when visualizing pathogenesis compared to other agents.
This new probe is the focus of Uddin’s Phi Beta Psi award, which will allow him to evaluate the use of FQ—encapsulated in a variety of nanoparticles—to use endoscopic optical imaging to detect colonic adenomas, a type of pre-cancerous tumor of the colon. Moreover, he will use the funds to verify that FQ fluoresces specifically in the presence of COX-2 and ROS in colorectal carcinogenesis. The development of FQ, as well as Uddin’s planned work with the nanoparticles, will create a framework for using the presence of COX-2 and ROS as biomarkers of neoplasia in the colon and will facilitate the development of the nanotechnology for the early detection, margin delineation, and surgical removal of colorectal cancer in patients.
*Uddin’s grant proposal was supported by Research Development and Support, which offers proposal development assistance for both private (foundations) and federally funded opportunities. Services include searches for new sponsors, coordination and team building for proposals of any size, content development, and draft review. RDS further supports faculty by building relationships with external sponsors, hosting workshops, and providing guides and language for common proposal requirements. RDS is in the Office of the Vice Provost for Research and Innovation. To learn more about RDS or request services, contact them at rds@vanderbilt.edu.
3. "What’s New in Science?" https://medschool.vanderbilt.edu/basic-sciences/2024/03/07/whats-new-in-science/
Detecting adenomas by colonoscopy remains one of the main preventative measures for colorectal cancer, with almost 100,000 adenomas identified during first-time screenings per year in the U.S. Unfortunately, using white-light colonoscopy—the clinical standard—without probing for a particular molecular marker of adenomas can lead to 30% of lesions going undetected. Md. Jashim Uddin, research associate professor of biochemistry, Larry Marnett, Mary Geddes Stahlman Professor of Cancer Research and university distinguished professor of biochemistry, and colleagues chose to use cyclooxygenase-2 or COX-2, an enzyme that increases inflammation and that is upregulated in preneoplastic lesions and colorectal cancer, as the marker to target when developing a fluorescent imaging agent to improve adenoma detection.
This work, reported in the Journal of Biomedical Optics, signifies an advance in adenoma detection by colonoscopy, which could reduce the number of colorectal cancer cases considering that adenomas, precursor lesions, can be removed during colonoscopies. In 2010, the researchers discovered a fluorescent inhibitor of COX-2 called fluorocoxib A; it was the first COX-2-targeted molecular imaging agent for the in vivo fluorescence imaging of inflammation and cancer and has since been widely used in research in the U.S. and across the globe. Now, the authors sought to forge a path to the clinic and packaged fluorocoxib A into an FDA-approved polymer to improve delivery to the adenomas. Uddin and colleagues administered fluorocoxib A to mice before a colonoscopy, which allowed them to clearly identify colonic adenomas in mice containing elevated levels of COX-2 in the lesions. The colon tissues of normal mice were not illuminated with the fluorescent compound, indicative of the lack of lesions. Pre-dosing the mice with a non-fluorescent inhibitor of COX-2 or with a fluorescent molecule that does not inhibit COX-2 led to minimal labeling of adenomas. Packaging the COX-2 inhibitor in the FDA-approved polymer creates a tractable path for clinical trials that could ultimately impact adenoma detection for the millions who undergo colonoscopies every year across the country. Uddin, M.J., Niitsu, H., Coffey, R.J., Marnett, L.J. (2023). Development of Pluoronic nanoparticles of fluorocoxib A for endoscopic fluorescence imaging of colonic adenomas. J Biomed Opt. 2023;28(4):040501.
4. "Potential probe for early ovarian cancer." https://news.vumc.org/2019/06/20/imaging-probe-ovarian-cancer/
Ovarian cancer is the fifth leading cause of cancer death in women and one of the most difficult malignancies to detect at an early stage. Emerging clinical evidence suggests that the enzyme cyclooxygenase-1 (COX-1) contributes significantly to tumorigenesis in ovarian cancer. Thus COX-1 could serve as a novel target for molecular imaging probes to improve early detection and response to treatment. Now in the American Chemical Society journal ACS Omega, Md. Jashim Uddin, PhD, Lawrence Marnett, PhD, and colleagues report the discovery of FDF, a furanone-based novel COX-1 selective inhibitor with adequate properties to enable its use for in vivo imaging. In two distinct animal models of ovarian cancer, xenografts expressing high levels of COX-1 demonstrated targeted uptake of the compound containing the F-18 radioisotope (18F-FDF) compared to tissues expressing low protein levels. This indicates that 18F-FDF may be the first feasible radiotracer validated for targeted PET/CT imaging of neoplastic tissues that express elevated levels of the COX-1 enzyme. The work was featured in the journal as an ACS Editors’ Choice and was supported by grants from the National Institutes of Health (CA128323, CA182850, CA136465, CA089450) and Kay Yow Cancer Fund/V Foundation.
5. "Fluorescent compounds make tumors glow." https://www.sciencedaily.com/releases/2010/04/100429082357.htm
6. "Jashim Uddin has received the prestigious Phi Beta Psi national research award." https://en.ittefaq.com.bd/6159/uddin-receives-a-second-phi-beta-psi-national
7. "Better adenoma detection." https://www.nashvillemedicalnews.com/article/6020/better-adenoma-detection
8. "Challenge puts technology transfer ingenuity on display." https://lab.vanderbilt.edu/jashim-uddin/wp-content/uploads/sites/105/2021/06/%E2%80%98Challenge%E2%80%99-puts-technology-transfer-ingenuity-on-display-VUMC-Reporter-Vanderbilt-University.pdf
9. "Detecting Ovarian cancer earlier." https://cdn.vanderbilt.edu/vu-web/lab-wpcontent/sites/105/2021/05/03213331/1-Discover-Jul312019.pdf
10. "Diagnosing and differentiating cancer at the molecular level." https://cdn.vanderbilt.edu/vu-web/lab-wpcontent/sites/105/2021/05/04152753/CTScan-Nov72011.pdf
Contact:
615-484-8674
jashim.uddin@vanderbilt.edu
https://wag.app.vanderbilt.edu/PublicPage/Faculty/Details/33074
Research Keywords
Fluorescent and radiolabeled cyclooxygense-2 inhibitors; in vivo imaging; structural basis, pharmacokinetics and metabolism.
Publications
Asaduzzaman A, Thompson CC, Uddin MJ. Machine Learning Approaches for Skin Neoplasm Diagnosis. ACS Omega. 2024 Jul 7/8/2024; DOI: 10.1021/acsomega.4c03640.
Uddin MJ, et al. Polymeric Micellar Nanoparticles Enable Image-guided Drug Delivery in Solid Tumors. BioRxiv. 2024 Jun 6/7/2024; DOI: 10.1101/2024.06.07.598019.
Asaduzzaman A, Thompson CC, Uddin MJ. Machine Learning Approaches for Skin Neoplasm Diagnosis. BioRxiv. 2024 May 5/12/2024; DOI: 10.1101/2024.05.12.593773.
Uddin MJ, Niitsu H, Coffey RJ, Marnett LJ. Development of Pluoronic nanoparticles of fluorocoxib A for endoscopic fluorescence imaging of colonic adenomas [letter]. J Biomed Opt [print-electronic]. 2023 Apr; 28(4): 40501. PMID: 37091910, PMCID: PMC10118138, PII: 220308LR, DOI: 10.1117/1.JBO.28.4.040501, ISSN: 1560-2281.
Aleem AM, Kang W, Lin S, Milad M, Kingsley PJ, Crews BC, Uddin MJ, Rouzer CA, Marnett LJ. Ferroptosis Inhibitors Suppress Prostaglandin Synthesis in Lipopolysaccharide-Stimulated Macrophages. ACS Chem Biol [print-electronic]. 2023 Jan 1/13/2023; PMID: 36638351, DOI: 10.1021/acschembio.2c00869, ISSN: 1554-8937.
Uddin MJ, Lo JH, Oltman CG, Crews BC, Huda T, Liu J, Kingsley PJ, Lin S, Milad M, Aleem AM, Asaduzzaman A, McIntyre JO, Duvall CL, Marnett LJ. Discovery of a Redox-Activatable Chemical Probe for Detection of Cyclooxygenase-2 in Cells and Animals. ACS Chem Biol [print-electronic]. 2022 Jul 7/15/2022; 17(7): 1714-22. PMID: 35786843, DOI: 10.1021/acschembio.1c00961, ISSN: 1554-8937.
Winters ND, Bedse G, Astafyev AA, Patrick TA, Altemus M, Morgan AJ, Mukerjee S, Johnson KD, Mahajan VR, Uddin MJ, Kingsley PJ, Centanni SW, Siciliano CA, Samuels DC, Marnett LJ, Winder DG, Patel S. Targeting diacylglycerol lipase reduces alcohol consumption in preclinical models. J Clin Invest [print-electronic]. 2021 Jul 7/22/2021; 131(17): PMID: 34292886, PMCID: PMC8409586, PII: e146861, DOI: 10.1172/JCI146861, ISSN: 1558-8238.
Malerba P, Crews BC, Ghebreselasie K, Daniel CK, Jashim E, Aleem AM, Salam RA, Marnett LJ, Uddin MJ. Targeted Detection of Cyclooxygenase-1 in Ovarian Cancer. ACS Med Chem Lett. 2020 Oct 10/8/2020; 11(10): 1837-42. PMID: 33062161, PMCID: PMC7549111, DOI: 10.1021/acsmedchemlett.9b00280, ISSN: 1948-5875.
Uddin MJ, Xu S, Crews BC, Aleem AM, Ghebreselasie K, Banerjee S, Marnett LJ. Harmaline Analogs as Substrate-Selective Cyclooxygenase-2 Inhibitors. ACS Med Chem Lett. 2020 Oct 10/8/2020; 11(10): 1881-5. PMID: 33062168, PMCID: PMC7549255, DOI: 10.1021/acsmedchemlett.9b00555, ISSN: 1948-5875.
Uddin MJ, Vemulapalli A, Niitsu H, Crews BC, Oltman CG, Kingsley PJ, Kavanaugh TE, Bedingfield SK, Mcintyre JO, Milad M, Aleem AM, Coffey RJ, Duvall CL, Marnett LJ. Molecular Imaging of Inflammation in Osteoarthritis Using a Water-Soluble Fluorocoxib. ACS Med Chem Lett. 2020 Oct 10/8/2020; 11(10): 1875-80. PMID: 33062167, PMCID: PMC7549260, DOI: 10.1021/acsmedchemlett.9b00512, ISSN: 1948-5875.
Cekanova M, Pandey S, Olin S, Ryan P, Stokes JE, Hecht S, Martin-Jimenez T, Uddin MJ, Marnett LJ. Pharmacokinetic characterization of fluorocoxib D, a cyclooxygenase-2-targeted optical imaging agent for detection of cancer. J Biomed Opt. 2020 Aug; 25(8): PMID: 32860356, PMCID: PMC7456637, PII: JBO-200044R, DOI: 10.1117/1.JBO.25.8.086005, ISSN: 1560-2281.
Bourn J, Rathore K, Donnell R, White W, Uddin MJ, Marnett L, Cekanova M. Detection of carcinogen-induced bladder cancer by fluorocoxib A. BMC Cancer. 2019 Nov 11/27/2019; 19(1): 1152. PMID: 31775672, PMCID: PMC6882158, PII: 10.1186/s12885-019-6366-x, DOI: 10.1186/s12885-019-6366-x, ISSN: 1471-2407.
Uddin MJ, Wilson AJ, Crews BC, Malerba P, Uddin MI, Kingsley PJ, Ghebreselasie K, Daniel CK, Nickels ML, Tantawy MN, Jashim E, Manning HC, Khabele D, Marnett LJ. Discovery of Furanone-Based Radiopharmaceuticals for Diagnostic Targeting of COX-1 in Ovarian Cancer. ACS Omega [print-electronic]. 2019 May 5/31/2019; 4(5): 9251-61. PMID: 31172046, PMCID: PMC6545551, DOI: 10.1021/acsomega.9b01093, ISSN: 2470-1343.
Xu S, Uddin MJ, Banerjee S, Duggan K, Musee J, Kiefer JR, Ghebreselasie K, Rouzer CA, Marnett LJ. Conjugated Indomethacin Fluorescent Inhibitors Utilize the Membrane Binding Domain of Cyclooxygenase-2 to Accommodate the Tethered Moiety. J. Biol. Chem. 2019 Apr 4/30/2019; 294(22): 8690-8. PMID: 31000626.
Bourn J, Pandey S, Uddin MJ, Marnett LJ, Cekanova M. Detection of tyrosine kinase inhibitors-induced COX-2 expression in bladder cancer by fluorocoxib A. Oncotarget. 2019 Jan 1/29/2019; 10(48).
Shaheen SM, Azad AK, Rahman MM, Uddin MJ. A comparative transgene expression study between a protaplex and a rotaplex embedded lipid-nanoparticles in murine derived dendritic cell. J Interdiscipl Nanomed. 2018 Jul 7/10/2018; 0(0).
Cavener VS, Gaulden A, Pennipede D, Jagasia P, Uddin J, Marnett LJ, Patel S. Inhibition of Diacylglycerol Lipase Impairs Fear Extinction in Mice. Front Neurosci. 2018; 12: 479. PMID: 30108473, PMCID: PMC6080414, DOI: 10.3389/fnins.2018.00479, ISSN: 1662-4548.
Bedse G, Hartley ND, Neale E, Gaulden AD, Patrick TA, Kingsley PJ, Uddin MJ, Plath N, Marnett LJ, Patel S. Functional Redundancy Between Canonical Endocannabinoid Signaling Systems in the Modulation of Anxiety. Biol. Psychiatry [print-electronic]. 2017 Oct 10/1/2017; 82(7): 488-99. PMID: 28438413, PMCID: PMC5585044, PII: S0006-3223(17)31357-4, DOI: 10.1016/j.biopsych.2017.03.002, ISSN: 1873-2402.
Bluett RJ, Báldi R, Haymer A, Gaulden AD, Hartley ND, Parrish WP, Baechle J, Marcus DJ, Mardam-Bey R, Shonesy BC, Uddin MJ, Marnett LJ, Mackie K, Colbran RJ, Winder DG, Patel S. Endocannabinoid signalling modulates susceptibility to traumatic stress exposure. Nat Commun. 2017 Mar 3/28/2017; 8: 14782. PMID: 28348378, PMCID: PMC5379055, PII: ncomms14782, DOI: 10.1038/ncomms14782, ISSN: 2041-1723.
Foster DJ, Wilson JM, Remke DH, Mahmood MS, Uddin MJ, Wess J, Patel S, Marnett LJ, Niswender CM, Jones CK, Xiang Z, Lindsley CW, Rook JM, Conn PJ. Antipsychotic-like Effects of M4 Positive Allosteric Modulators Are Mediated by CB2 Receptor-Dependent Inhibition of Dopamine Release. Neuron [print-electronic]. 2016 Sep 9/21/2016; 91(6): 1244-52. PMID: 27618677, PII: S0896-6273(16)30509-8, DOI: 10.1016/j.neuron.2016.08.017, ISSN: 1097-4199.
Uddin MJ, Crews BC, Xu S, Ghebreselasie K, Daniel CK, Kingsley PJ, Banerjee S, Marnett LJ. Antitumor Activity of Cytotoxic Cyclooxygenase-2 Inhibitors. ACS Chem. Biol [print-electronic]. 2016 Sep 9/19/2016; PMID: 27588346, DOI: 10.1021/acschembio.6b00560, ISSN: 1554-8937.
Uddin MJ, Moore CE, Crews BC, Daniel CK, Ghebreselasie K, McIntyre JO, Marnett LJ, Jayagopal A. Fluorocoxib A enables targeted detection of cyclooxygenase-2 in laser-induced choroidal neovascularization. J Biomed Opt. 2016 Sep 9/1/2016; 21(9): 90503. PMID: 27626899, PII: 2553360, DOI: 10.1117/1.JBO.21.9.090503, ISSN: 1560-2281.
Adeniji A, Uddin MJ, Zang T, Tamae D, Wangtrakuldee P, Marnett LJ, Penning TM. Discovery of (R)-2-(6-Methoxynaphthalen-2-yl)butanoic Acid as a Potent and Selective Aldo-keto Reductase 1C3 Inhibitor. J. Med. Chem [print-electronic]. 2016 Aug 8/25/2016; 59(16): 7431-44. PMID: 27486833, DOI: 10.1021/acs.jmedchem.6b00160, ISSN: 1520-4804.
Uddin MJ, Werfel TA, Crews BC, Gupta MK, Kavanaugh TE, Kingsley PJ, Boyd K, Marnett LJ, Duvall CL. Fluorocoxib A loaded nanoparticles enable targeted visualization of cyclooxygenase-2 in inflammation and cancer. Biomaterials [print-electronic]. 2016 Jun; 92: 71-80. PMID: 27043768, PMCID: PMC4833621, PII: S0142-9612(16)30049-7, DOI: 10.1016/j.biomaterials.2016.03.028, ISSN: 1878-5905.
Uddin MI, Evans SM, Craft JR, Capozzi ME, McCollum GW, Yang R, Marnett LJ, Uddin MJ, Jayagopal A, Penn JS. In Vivo Imaging of Retinal Hypoxia in a Model of Oxygen-Induced Retinopathy. Sci Rep. 2016; 6: 31011. PMID: 27491345, PMCID: PMC4974503, PII: srep31011, DOI: 10.1038/srep31011, ISSN: 2045-2322.
Wilson AJ, Fadare O, Beeghly-Fadiel A, Son DS, Liu Q, Zhao S, Saskowski J, Uddin MJ, Daniel C, Crews B, Lehmann BD, Pietenpol JA, Crispens MA, Marnett LJ, Khabele D. Aberrant over-expression of COX-1 intersects multiple pro-tumorigenic pathways in high-grade serous ovarian cancer. Oncotarget. 2015 Aug 8/28/2015; 6(25): 21353-68. PMID: 25972361, PMCID: PMC4673270, PII: 3860, DOI: 10.18632/oncotarget.3860, ISSN: 1949-2553.
Uddin MI, Evans SM, Craft JR, Marnett LJ, Uddin MJ, Jayagopal A. Applications of azo-based probes for imaging retinal hypoxia. ACS Med Chem Lett. 2015 Apr 4/9/2015; 6(4): 445-9. PMID: 25893047, PMCID: PMC4394343, DOI: 10.1021/ml5005206, ISSN: 1948-5875.
Ra H, González-González E, Uddin MJ, King BL, Lee A, Ali-Khan I, Marnett LJ, Tang JY, Contag CH. Detection of non-melanoma skin cancer by in vivo fluorescence imaging with fluorocoxib A. Neoplasia. 2015 Feb; 17(2): 201-7. PMID: 25748239, PMCID: PMC4351298, PII: S1476-5586(14)00199-7, DOI: 10.1016/j.neo.2014.12.009, ISSN: 1476-5586.
Uddin MJ, Elleman AV, Ghebreselasie K, Daniel CK, Crews BC, Nance KD, Huda T, Marnett LJ. Design of Fluorine-Containing 3,4-Diarylfuran-2(5H)-ones as Selective COX-1 Inhibitors. ACS Med Chem Lett. 2014 Nov 11/13/2014; 5(11): 1254-8. PMID: 25408841, PMCID: PMC4233350, DOI: 10.1021/ml500344j, ISSN: 1948-5875.
Perrone MG, Malerba P, Uddin MJ, Vitale P, Panella A, Crews BC, Daniel CK, Ghebreselasie K, Nickels M, Tantawy MN, Manning HC, Marnett LJ, Scilimati A. PET radiotracer [¹8F]-P6 selectively targeting COX-1 as a novel biomarker in ovarian cancer: preliminary investigation. Eur J Med Chem [print-electronic]. 2014 Jun 6/10/2014; 80: 562-8. PMID: 24832612, PMCID: PMC4401082, PII: S0223-5234(14)00403-6, DOI: 10.1016/j.ejmech.2014.04.074, ISSN: 1768-3254.
Uddin MJ, Crews BC, Huda I, Ghebreselasie K, Daniel CK, Marnett LJ. Trifluoromethyl fluorocoxib a detects cyclooxygenase-2 expression in inflammatory tissues and human tumor xenografts. ACS Med Chem Lett. 2014 Apr 4/10/2014; 5(4): 446-50. PMID: 24900856, PMCID: PMC4027729, DOI: 10.1021/ml400485g, ISSN: 1948-5875.
Blobaum AL, Uddin MJ, Felts AS, Crews BC, Rouzer CA, Marnett LJ. The 2'-Trifluoromethyl Analogue of Indomethacin Is a Potent and Selective COX-2 Inhibitor. ACS Med Chem Lett [print-electronic]. 2013 May 5/9/2013; 4(5): 486-90. PMID: 23687559, PMCID: PMC3654564, DOI: 10.1021/ml400066a, ISSN: 1948-5875.
Uddin MJ, Crews BC, Ghebreselasie K, Marnett LJ. Design, synthesis, and structure-activity relationship studies of fluorescent inhibitors of cycloxygenase-2 as targeted optical imaging agents. Bioconjug. Chem [print-electronic]. 2013 Apr 4/17/2013; 24(4): 712-23. PMID: 23488616, PMCID: PMC3630741, DOI: 10.1021/bc300693w, ISSN: 1520-4812.
Uddin MJ, Crews BC, Ghebreselasie K, Huda I, Kingsley PJ, Ansari MS, Tantawy MN, Reese J, Marnett LJ. Fluorinated COX-2 inhibitors as agents in PET imaging of inflammation and cancer. Cancer Prev Res (Phila) [print-electronic]. 2011 Oct; 4(10): 1536-45. PMID: 21900596, PMCID: PMC3214660, PII: 1940-6207.CAPR-11-0120, DOI: 10.1158/1940-6207.CAPR-11-0120, ISSN: 1940-6215.
Uddin MJ, Schulte MI, Maddukuri L, Harp J, Marnett LJ. Semisynthesis of 6-chloropurine-2'-deoxyriboside 5'-dimethoxytrityl 3'-(2-cyanoethyl-N,N-diisopropylamino)phosphoramidite and its use in the synthesis of fluorescently labeled oligonucleotides. Nucleosides Nucleotides Nucleic Acids. 2010 Nov; 29(11): 831-40. PMID: 21128170, PMCID: PMC3019237, PII: 930388354, DOI: 10.1080/15257770.2010.530332, ISSN: 1532-2335.
Uddin MJ, Crews BC, Blobaum AL, Kingsley PJ, Gorden DL, McIntyre JO, Matrisian LM, Subbaramaiah K, Dannenberg AJ, Piston DW, Marnett LJ. Selective visualization of cyclooxygenase-2 in inflammation and cancer by targeted fluorescent imaging agents. Cancer Res. 2010 May 5/1/2010; 70(9): 3618-27. PMID: 20430759, PMCID: PMC2864539, PII: 70/9/3618, DOI: 10.1158/0008-5472.CAN-09-2664, ISSN: 1538-7445.
Uddin MJ, Smithson DC, Brown KM, Crews BC, Connelly M, Zhu F, Marnett LJ, Guy RK. Podophyllotoxin analogues active versus Trypanosoma brucei. Bioorg. Med. Chem. Lett [print-electronic]. 2010 Mar 3/1/2010; 20(5): 1787-91. PMID: 20129783, PMCID: PMC2826502, PII: S0960-894X(10)00011-9, DOI: 10.1016/j.bmcl.2010.01.009, ISSN: 1464-3405.
Konkle ME, Hargrove TY, Kleshchenko YY, von Kries JP, Ridenour W, Uddin MJ, Caprioli RM, Marnett LJ, Nes WD, Villalta F, Waterman MR, Lepesheva GI. Indomethacin amides as a novel molecular scaffold for targeting Trypanosoma cruzi sterol 14alpha-demethylase. J. Med. Chem. 2009 May 5/14/2009; 52(9): 2846-53. PMID: 19354253, PMCID: PMC2744100, DOI: 10.1021/jm801643b, ISSN: 1520-4804.
Uddin, M. J., Crews, B. C., Blobaum, A. L., Kingslay, P. J., Ghebraselase, K., Saleh, S. S., Clanton, J. A., Baldwin, R. M. and Marnett, L. J.. Synthesis and evaluation of [123I]-indomethacin derivatives as COX-2 targeted imaging agents. Journal of Labelled Compounds and Radiopharmaceuticals. 2009; 52: 387-93.
Uddin MJ, Marnett LJ. Synthesis of 5- and 6-carboxy-X-rhodamines. Org. Lett [print-electronic]. 2008 Nov 11/6/2008; 10(21): 4799-801. PMID: 18837556, PMCID: PMC2646678, DOI: 10.1021/ol801904k, ISSN: 1523-7052.
Anning, P. B.; Coles, B; Morton, J.; Wang, H.; Uddin, M. J.; Morrow, J. D.; Dey, S. K.; Marnett, L. J.; Odonnell, V. B.. Nitric oxide deficiency promotes vascular side effects of cyclooxygenase inhibitors. Blood. 2006; 13: 4059.
Uddin MJ, Rao PN, McDonald R, Knaus EE. Design and synthesis of (E)-1,1,2-triarylethenes: novel inhibitors of the cyclooxygenase-2 (COX-2) isozyme. Bioorg. Med. Chem. Lett. 2005 Jan 1/17/2005; 15(2): 439-42. PMID: 15603969, PII: S0960-894X(04)01291-0, DOI: 10.1016/j.bmcl.2004.10.050, ISSN: 0960-894X.
Uddin MJ, Praveen Rao PN, Knaus EE. Design and synthesis of (Z)-1,2-diphenyl-1-(4-methanesulfonamidophenyl)alk-1-enes and (Z)-1-(4-azidophenyl)-1,2-diphenylalk-1-enes: novel inhibitors of cyclooxygenase-2 (COX-2) with anti-inflammatory and analgesic activity. Bioorg. Med. Chem. 2005 Jan 1/17/2005; 13(2): 417-24. PMID: 15598562, PII: S0968-0896(04)00791-6, DOI: 10.1016/j.bmc.2004.10.017, ISSN: 0968-0896.
Uddin MJ, Praveen Rao PN, McDonald R, Knaus EE. A new class of acyclic 2-alkyl-1,1,2-triaryl (Z)-olefins as selective cyclooxygenase-2 inhibitors. J. Med. Chem. 2004 Nov 11/18/2004; 47(24): 6108-11. PMID: 15537365, DOI: 10.1021/jm049523y, ISSN: 0022-2623.
Uddin MJ, Rao PN, Knaus EE. Design and synthesis of acyclic triaryl (Z)-olefins: a novel class of cyclooxygenase-2 (COX-2) inhibitors. Bioorg. Med. Chem. 2004 Nov 11/15/2004; 12(22): 5929-40. PMID: 15498669, PII: S0968-0896(04)00624-8, DOI: 10.1016/j.bmc.2004.08.021, ISSN: 0968-0896.
Uddin MJ, Rao PN, Rahim MA, McDonald R, Knaus EE. A new class of acyclic 2-alkyl-1,2-diaryl (E)-olefins as selective cyclooxygenase-2 (COX-2) inhibitors. Bioorg. Med. Chem. Lett. 2004 Oct 10/4/2004; 14(19): 4911-4. PMID: 15341950, PII: S0960-894X(04)00919-9, DOI: 10.1016/j.bmcl.2004.07.027, ISSN: 0960-894X.
Rao PN, Uddin MJ, Knaus EE. Design, synthesis, and structure-activity relationship studies of 3,4,6-triphenylpyran-2-ones as selective cyclooxygenase-2 inhibitors. J. Med. Chem. 2004 Jul 7/29/2004; 47(16): 3972-90. PMID: 15267236, DOI: 10.1021/jm049939b, ISSN: 0022-2623.
Uddin MJ, Rao PN, Knaus EE. Design of acyclic triaryl olefins: a new class of potent and selective cyclooxygenase-2 (COX-2) inhibitors. Bioorg. Med. Chem. Lett. 2004 Apr 4/19/2004; 14(8): 1953-6. PMID: 15050635, PII: S0960894X04001556, DOI: 10.1016/j.bmcl.2004.01.075, ISSN: 0960-894X.
Uddin, M. J.; Rao, P. N. P.; Knaus, E. E.. Methylsulfonyl and Hydroxyl Substituents Induce (Z)-Stereocontrol in the McMurry Olefination Reaction. Synlett. 2004; 1513.
Uddin MJ, Rao PN, Knaus EE. Design and synthesis of novel celecoxib analogues as selective cyclooxygenase-2 (COX-2) inhibitors: replacement of the sulfonamide pharmacophore by a sulfonylazide bioisostere. Bioorg. Med. Chem. 2003 Nov 11/17/2003; 11(23): 5273-80. PMID: 14604691, PII: S0968089603005583, ISSN: 0968-0896.
Uddin, M. J.; Rao, P. N. P.; Knaus, E. E. Design, Synthesis and Biological Evaluation of Novel Rofecoxib Analogs as Potential Cyclooxygenase-2 (COX-2) Inhibitors: Replacement of Methylsulfonyl Pharmacophore by a Sulfonylazide Bioisostre. Journal of Heterocyclic Chemistry. 2003; 40: 861.
Uddin, M. J.; Kikuchi, M.; Takedatsu, K.; Arai, K.-I.; Fujimoto, T.; Motoyoshiya, J.; Kakehi, A.; Iriue, R.; Shirai, H.; Yamamoto, I.. Synthesis and Structure of Condensed Heterocycles Derived from Intramolecular 1,3-Dipolar Cycloaddition of Transient and Enantiomerically Pure ?-Allylamino Nitrones and Nitrile Oxides in a High Level of Diastereoselectivity. Synthesis. 2000; 365.
Uddin, M. J.; Fujimoto, T.; Kakehi, A.; Shirai, H.; Yamamoto, I.. Diastereoselective Synthesis of Bridgehead Heterocyclic Spiro Compounds Derived from Tandem Michael Intramolecular 1,3-Dipolar Cycloaddition of Nitrones. Heterocyclic Communications. 2000; 6: 113.
Uddin, M. J.; Shinooka, A.; Fujimoto, T.; Shirai, H.; Yamamoto, I.. Isoxazolidine Based New Chral Auxiliary for Asymmetric Synthesis. Heterocyclic Communications. 2000; 6: 505.
Uddin MJ, et al. Polymeric Micellar Nanoparticles Enable Image-guided Drug Delivery in Solid Tumors. BioRxiv. 2024 Jun 6/7/2024; DOI: 10.1101/2024.06.07.598019.
Asaduzzaman A, Thompson CC, Uddin MJ. Machine Learning Approaches for Skin Neoplasm Diagnosis. BioRxiv. 2024 May 5/12/2024; DOI: 10.1101/2024.05.12.593773.
Uddin MJ, Niitsu H, Coffey RJ, Marnett LJ. Development of Pluoronic nanoparticles of fluorocoxib A for endoscopic fluorescence imaging of colonic adenomas [letter]. J Biomed Opt [print-electronic]. 2023 Apr; 28(4): 40501. PMID: 37091910, PMCID: PMC10118138, PII: 220308LR, DOI: 10.1117/1.JBO.28.4.040501, ISSN: 1560-2281.
Aleem AM, Kang W, Lin S, Milad M, Kingsley PJ, Crews BC, Uddin MJ, Rouzer CA, Marnett LJ. Ferroptosis Inhibitors Suppress Prostaglandin Synthesis in Lipopolysaccharide-Stimulated Macrophages. ACS Chem Biol [print-electronic]. 2023 Jan 1/13/2023; PMID: 36638351, DOI: 10.1021/acschembio.2c00869, ISSN: 1554-8937.
Uddin MJ, Lo JH, Oltman CG, Crews BC, Huda T, Liu J, Kingsley PJ, Lin S, Milad M, Aleem AM, Asaduzzaman A, McIntyre JO, Duvall CL, Marnett LJ. Discovery of a Redox-Activatable Chemical Probe for Detection of Cyclooxygenase-2 in Cells and Animals. ACS Chem Biol [print-electronic]. 2022 Jul 7/15/2022; 17(7): 1714-22. PMID: 35786843, DOI: 10.1021/acschembio.1c00961, ISSN: 1554-8937.
Winters ND, Bedse G, Astafyev AA, Patrick TA, Altemus M, Morgan AJ, Mukerjee S, Johnson KD, Mahajan VR, Uddin MJ, Kingsley PJ, Centanni SW, Siciliano CA, Samuels DC, Marnett LJ, Winder DG, Patel S. Targeting diacylglycerol lipase reduces alcohol consumption in preclinical models. J Clin Invest [print-electronic]. 2021 Jul 7/22/2021; 131(17): PMID: 34292886, PMCID: PMC8409586, PII: e146861, DOI: 10.1172/JCI146861, ISSN: 1558-8238.
Malerba P, Crews BC, Ghebreselasie K, Daniel CK, Jashim E, Aleem AM, Salam RA, Marnett LJ, Uddin MJ. Targeted Detection of Cyclooxygenase-1 in Ovarian Cancer. ACS Med Chem Lett. 2020 Oct 10/8/2020; 11(10): 1837-42. PMID: 33062161, PMCID: PMC7549111, DOI: 10.1021/acsmedchemlett.9b00280, ISSN: 1948-5875.
Uddin MJ, Xu S, Crews BC, Aleem AM, Ghebreselasie K, Banerjee S, Marnett LJ. Harmaline Analogs as Substrate-Selective Cyclooxygenase-2 Inhibitors. ACS Med Chem Lett. 2020 Oct 10/8/2020; 11(10): 1881-5. PMID: 33062168, PMCID: PMC7549255, DOI: 10.1021/acsmedchemlett.9b00555, ISSN: 1948-5875.
Uddin MJ, Vemulapalli A, Niitsu H, Crews BC, Oltman CG, Kingsley PJ, Kavanaugh TE, Bedingfield SK, Mcintyre JO, Milad M, Aleem AM, Coffey RJ, Duvall CL, Marnett LJ. Molecular Imaging of Inflammation in Osteoarthritis Using a Water-Soluble Fluorocoxib. ACS Med Chem Lett. 2020 Oct 10/8/2020; 11(10): 1875-80. PMID: 33062167, PMCID: PMC7549260, DOI: 10.1021/acsmedchemlett.9b00512, ISSN: 1948-5875.
Cekanova M, Pandey S, Olin S, Ryan P, Stokes JE, Hecht S, Martin-Jimenez T, Uddin MJ, Marnett LJ. Pharmacokinetic characterization of fluorocoxib D, a cyclooxygenase-2-targeted optical imaging agent for detection of cancer. J Biomed Opt. 2020 Aug; 25(8): PMID: 32860356, PMCID: PMC7456637, PII: JBO-200044R, DOI: 10.1117/1.JBO.25.8.086005, ISSN: 1560-2281.
Bourn J, Rathore K, Donnell R, White W, Uddin MJ, Marnett L, Cekanova M. Detection of carcinogen-induced bladder cancer by fluorocoxib A. BMC Cancer. 2019 Nov 11/27/2019; 19(1): 1152. PMID: 31775672, PMCID: PMC6882158, PII: 10.1186/s12885-019-6366-x, DOI: 10.1186/s12885-019-6366-x, ISSN: 1471-2407.
Uddin MJ, Wilson AJ, Crews BC, Malerba P, Uddin MI, Kingsley PJ, Ghebreselasie K, Daniel CK, Nickels ML, Tantawy MN, Jashim E, Manning HC, Khabele D, Marnett LJ. Discovery of Furanone-Based Radiopharmaceuticals for Diagnostic Targeting of COX-1 in Ovarian Cancer. ACS Omega [print-electronic]. 2019 May 5/31/2019; 4(5): 9251-61. PMID: 31172046, PMCID: PMC6545551, DOI: 10.1021/acsomega.9b01093, ISSN: 2470-1343.
Xu S, Uddin MJ, Banerjee S, Duggan K, Musee J, Kiefer JR, Ghebreselasie K, Rouzer CA, Marnett LJ. Conjugated Indomethacin Fluorescent Inhibitors Utilize the Membrane Binding Domain of Cyclooxygenase-2 to Accommodate the Tethered Moiety. J. Biol. Chem. 2019 Apr 4/30/2019; 294(22): 8690-8. PMID: 31000626.
Bourn J, Pandey S, Uddin MJ, Marnett LJ, Cekanova M. Detection of tyrosine kinase inhibitors-induced COX-2 expression in bladder cancer by fluorocoxib A. Oncotarget. 2019 Jan 1/29/2019; 10(48).
Shaheen SM, Azad AK, Rahman MM, Uddin MJ. A comparative transgene expression study between a protaplex and a rotaplex embedded lipid-nanoparticles in murine derived dendritic cell. J Interdiscipl Nanomed. 2018 Jul 7/10/2018; 0(0).
Cavener VS, Gaulden A, Pennipede D, Jagasia P, Uddin J, Marnett LJ, Patel S. Inhibition of Diacylglycerol Lipase Impairs Fear Extinction in Mice. Front Neurosci. 2018; 12: 479. PMID: 30108473, PMCID: PMC6080414, DOI: 10.3389/fnins.2018.00479, ISSN: 1662-4548.
Bedse G, Hartley ND, Neale E, Gaulden AD, Patrick TA, Kingsley PJ, Uddin MJ, Plath N, Marnett LJ, Patel S. Functional Redundancy Between Canonical Endocannabinoid Signaling Systems in the Modulation of Anxiety. Biol. Psychiatry [print-electronic]. 2017 Oct 10/1/2017; 82(7): 488-99. PMID: 28438413, PMCID: PMC5585044, PII: S0006-3223(17)31357-4, DOI: 10.1016/j.biopsych.2017.03.002, ISSN: 1873-2402.
Bluett RJ, Báldi R, Haymer A, Gaulden AD, Hartley ND, Parrish WP, Baechle J, Marcus DJ, Mardam-Bey R, Shonesy BC, Uddin MJ, Marnett LJ, Mackie K, Colbran RJ, Winder DG, Patel S. Endocannabinoid signalling modulates susceptibility to traumatic stress exposure. Nat Commun. 2017 Mar 3/28/2017; 8: 14782. PMID: 28348378, PMCID: PMC5379055, PII: ncomms14782, DOI: 10.1038/ncomms14782, ISSN: 2041-1723.
Foster DJ, Wilson JM, Remke DH, Mahmood MS, Uddin MJ, Wess J, Patel S, Marnett LJ, Niswender CM, Jones CK, Xiang Z, Lindsley CW, Rook JM, Conn PJ. Antipsychotic-like Effects of M4 Positive Allosteric Modulators Are Mediated by CB2 Receptor-Dependent Inhibition of Dopamine Release. Neuron [print-electronic]. 2016 Sep 9/21/2016; 91(6): 1244-52. PMID: 27618677, PII: S0896-6273(16)30509-8, DOI: 10.1016/j.neuron.2016.08.017, ISSN: 1097-4199.
Uddin MJ, Crews BC, Xu S, Ghebreselasie K, Daniel CK, Kingsley PJ, Banerjee S, Marnett LJ. Antitumor Activity of Cytotoxic Cyclooxygenase-2 Inhibitors. ACS Chem. Biol [print-electronic]. 2016 Sep 9/19/2016; PMID: 27588346, DOI: 10.1021/acschembio.6b00560, ISSN: 1554-8937.
Uddin MJ, Moore CE, Crews BC, Daniel CK, Ghebreselasie K, McIntyre JO, Marnett LJ, Jayagopal A. Fluorocoxib A enables targeted detection of cyclooxygenase-2 in laser-induced choroidal neovascularization. J Biomed Opt. 2016 Sep 9/1/2016; 21(9): 90503. PMID: 27626899, PII: 2553360, DOI: 10.1117/1.JBO.21.9.090503, ISSN: 1560-2281.
Adeniji A, Uddin MJ, Zang T, Tamae D, Wangtrakuldee P, Marnett LJ, Penning TM. Discovery of (R)-2-(6-Methoxynaphthalen-2-yl)butanoic Acid as a Potent and Selective Aldo-keto Reductase 1C3 Inhibitor. J. Med. Chem [print-electronic]. 2016 Aug 8/25/2016; 59(16): 7431-44. PMID: 27486833, DOI: 10.1021/acs.jmedchem.6b00160, ISSN: 1520-4804.
Uddin MJ, Werfel TA, Crews BC, Gupta MK, Kavanaugh TE, Kingsley PJ, Boyd K, Marnett LJ, Duvall CL. Fluorocoxib A loaded nanoparticles enable targeted visualization of cyclooxygenase-2 in inflammation and cancer. Biomaterials [print-electronic]. 2016 Jun; 92: 71-80. PMID: 27043768, PMCID: PMC4833621, PII: S0142-9612(16)30049-7, DOI: 10.1016/j.biomaterials.2016.03.028, ISSN: 1878-5905.
Uddin MI, Evans SM, Craft JR, Capozzi ME, McCollum GW, Yang R, Marnett LJ, Uddin MJ, Jayagopal A, Penn JS. In Vivo Imaging of Retinal Hypoxia in a Model of Oxygen-Induced Retinopathy. Sci Rep. 2016; 6: 31011. PMID: 27491345, PMCID: PMC4974503, PII: srep31011, DOI: 10.1038/srep31011, ISSN: 2045-2322.
Wilson AJ, Fadare O, Beeghly-Fadiel A, Son DS, Liu Q, Zhao S, Saskowski J, Uddin MJ, Daniel C, Crews B, Lehmann BD, Pietenpol JA, Crispens MA, Marnett LJ, Khabele D. Aberrant over-expression of COX-1 intersects multiple pro-tumorigenic pathways in high-grade serous ovarian cancer. Oncotarget. 2015 Aug 8/28/2015; 6(25): 21353-68. PMID: 25972361, PMCID: PMC4673270, PII: 3860, DOI: 10.18632/oncotarget.3860, ISSN: 1949-2553.
Uddin MI, Evans SM, Craft JR, Marnett LJ, Uddin MJ, Jayagopal A. Applications of azo-based probes for imaging retinal hypoxia. ACS Med Chem Lett. 2015 Apr 4/9/2015; 6(4): 445-9. PMID: 25893047, PMCID: PMC4394343, DOI: 10.1021/ml5005206, ISSN: 1948-5875.
Ra H, González-González E, Uddin MJ, King BL, Lee A, Ali-Khan I, Marnett LJ, Tang JY, Contag CH. Detection of non-melanoma skin cancer by in vivo fluorescence imaging with fluorocoxib A. Neoplasia. 2015 Feb; 17(2): 201-7. PMID: 25748239, PMCID: PMC4351298, PII: S1476-5586(14)00199-7, DOI: 10.1016/j.neo.2014.12.009, ISSN: 1476-5586.
Uddin MJ, Elleman AV, Ghebreselasie K, Daniel CK, Crews BC, Nance KD, Huda T, Marnett LJ. Design of Fluorine-Containing 3,4-Diarylfuran-2(5H)-ones as Selective COX-1 Inhibitors. ACS Med Chem Lett. 2014 Nov 11/13/2014; 5(11): 1254-8. PMID: 25408841, PMCID: PMC4233350, DOI: 10.1021/ml500344j, ISSN: 1948-5875.
Perrone MG, Malerba P, Uddin MJ, Vitale P, Panella A, Crews BC, Daniel CK, Ghebreselasie K, Nickels M, Tantawy MN, Manning HC, Marnett LJ, Scilimati A. PET radiotracer [¹8F]-P6 selectively targeting COX-1 as a novel biomarker in ovarian cancer: preliminary investigation. Eur J Med Chem [print-electronic]. 2014 Jun 6/10/2014; 80: 562-8. PMID: 24832612, PMCID: PMC4401082, PII: S0223-5234(14)00403-6, DOI: 10.1016/j.ejmech.2014.04.074, ISSN: 1768-3254.
Uddin MJ, Crews BC, Huda I, Ghebreselasie K, Daniel CK, Marnett LJ. Trifluoromethyl fluorocoxib a detects cyclooxygenase-2 expression in inflammatory tissues and human tumor xenografts. ACS Med Chem Lett. 2014 Apr 4/10/2014; 5(4): 446-50. PMID: 24900856, PMCID: PMC4027729, DOI: 10.1021/ml400485g, ISSN: 1948-5875.
Blobaum AL, Uddin MJ, Felts AS, Crews BC, Rouzer CA, Marnett LJ. The 2'-Trifluoromethyl Analogue of Indomethacin Is a Potent and Selective COX-2 Inhibitor. ACS Med Chem Lett [print-electronic]. 2013 May 5/9/2013; 4(5): 486-90. PMID: 23687559, PMCID: PMC3654564, DOI: 10.1021/ml400066a, ISSN: 1948-5875.
Uddin MJ, Crews BC, Ghebreselasie K, Marnett LJ. Design, synthesis, and structure-activity relationship studies of fluorescent inhibitors of cycloxygenase-2 as targeted optical imaging agents. Bioconjug. Chem [print-electronic]. 2013 Apr 4/17/2013; 24(4): 712-23. PMID: 23488616, PMCID: PMC3630741, DOI: 10.1021/bc300693w, ISSN: 1520-4812.
Uddin MJ, Crews BC, Ghebreselasie K, Huda I, Kingsley PJ, Ansari MS, Tantawy MN, Reese J, Marnett LJ. Fluorinated COX-2 inhibitors as agents in PET imaging of inflammation and cancer. Cancer Prev Res (Phila) [print-electronic]. 2011 Oct; 4(10): 1536-45. PMID: 21900596, PMCID: PMC3214660, PII: 1940-6207.CAPR-11-0120, DOI: 10.1158/1940-6207.CAPR-11-0120, ISSN: 1940-6215.
Uddin MJ, Schulte MI, Maddukuri L, Harp J, Marnett LJ. Semisynthesis of 6-chloropurine-2'-deoxyriboside 5'-dimethoxytrityl 3'-(2-cyanoethyl-N,N-diisopropylamino)phosphoramidite and its use in the synthesis of fluorescently labeled oligonucleotides. Nucleosides Nucleotides Nucleic Acids. 2010 Nov; 29(11): 831-40. PMID: 21128170, PMCID: PMC3019237, PII: 930388354, DOI: 10.1080/15257770.2010.530332, ISSN: 1532-2335.
Uddin MJ, Crews BC, Blobaum AL, Kingsley PJ, Gorden DL, McIntyre JO, Matrisian LM, Subbaramaiah K, Dannenberg AJ, Piston DW, Marnett LJ. Selective visualization of cyclooxygenase-2 in inflammation and cancer by targeted fluorescent imaging agents. Cancer Res. 2010 May 5/1/2010; 70(9): 3618-27. PMID: 20430759, PMCID: PMC2864539, PII: 70/9/3618, DOI: 10.1158/0008-5472.CAN-09-2664, ISSN: 1538-7445.
Uddin MJ, Smithson DC, Brown KM, Crews BC, Connelly M, Zhu F, Marnett LJ, Guy RK. Podophyllotoxin analogues active versus Trypanosoma brucei. Bioorg. Med. Chem. Lett [print-electronic]. 2010 Mar 3/1/2010; 20(5): 1787-91. PMID: 20129783, PMCID: PMC2826502, PII: S0960-894X(10)00011-9, DOI: 10.1016/j.bmcl.2010.01.009, ISSN: 1464-3405.
Konkle ME, Hargrove TY, Kleshchenko YY, von Kries JP, Ridenour W, Uddin MJ, Caprioli RM, Marnett LJ, Nes WD, Villalta F, Waterman MR, Lepesheva GI. Indomethacin amides as a novel molecular scaffold for targeting Trypanosoma cruzi sterol 14alpha-demethylase. J. Med. Chem. 2009 May 5/14/2009; 52(9): 2846-53. PMID: 19354253, PMCID: PMC2744100, DOI: 10.1021/jm801643b, ISSN: 1520-4804.
Uddin, M. J., Crews, B. C., Blobaum, A. L., Kingslay, P. J., Ghebraselase, K., Saleh, S. S., Clanton, J. A., Baldwin, R. M. and Marnett, L. J.. Synthesis and evaluation of [123I]-indomethacin derivatives as COX-2 targeted imaging agents. Journal of Labelled Compounds and Radiopharmaceuticals. 2009; 52: 387-93.
Uddin MJ, Marnett LJ. Synthesis of 5- and 6-carboxy-X-rhodamines. Org. Lett [print-electronic]. 2008 Nov 11/6/2008; 10(21): 4799-801. PMID: 18837556, PMCID: PMC2646678, DOI: 10.1021/ol801904k, ISSN: 1523-7052.
Anning, P. B.; Coles, B; Morton, J.; Wang, H.; Uddin, M. J.; Morrow, J. D.; Dey, S. K.; Marnett, L. J.; Odonnell, V. B.. Nitric oxide deficiency promotes vascular side effects of cyclooxygenase inhibitors. Blood. 2006; 13: 4059.
Uddin MJ, Rao PN, McDonald R, Knaus EE. Design and synthesis of (E)-1,1,2-triarylethenes: novel inhibitors of the cyclooxygenase-2 (COX-2) isozyme. Bioorg. Med. Chem. Lett. 2005 Jan 1/17/2005; 15(2): 439-42. PMID: 15603969, PII: S0960-894X(04)01291-0, DOI: 10.1016/j.bmcl.2004.10.050, ISSN: 0960-894X.
Uddin MJ, Praveen Rao PN, Knaus EE. Design and synthesis of (Z)-1,2-diphenyl-1-(4-methanesulfonamidophenyl)alk-1-enes and (Z)-1-(4-azidophenyl)-1,2-diphenylalk-1-enes: novel inhibitors of cyclooxygenase-2 (COX-2) with anti-inflammatory and analgesic activity. Bioorg. Med. Chem. 2005 Jan 1/17/2005; 13(2): 417-24. PMID: 15598562, PII: S0968-0896(04)00791-6, DOI: 10.1016/j.bmc.2004.10.017, ISSN: 0968-0896.
Uddin MJ, Praveen Rao PN, McDonald R, Knaus EE. A new class of acyclic 2-alkyl-1,1,2-triaryl (Z)-olefins as selective cyclooxygenase-2 inhibitors. J. Med. Chem. 2004 Nov 11/18/2004; 47(24): 6108-11. PMID: 15537365, DOI: 10.1021/jm049523y, ISSN: 0022-2623.
Uddin MJ, Rao PN, Knaus EE. Design and synthesis of acyclic triaryl (Z)-olefins: a novel class of cyclooxygenase-2 (COX-2) inhibitors. Bioorg. Med. Chem. 2004 Nov 11/15/2004; 12(22): 5929-40. PMID: 15498669, PII: S0968-0896(04)00624-8, DOI: 10.1016/j.bmc.2004.08.021, ISSN: 0968-0896.
Uddin MJ, Rao PN, Rahim MA, McDonald R, Knaus EE. A new class of acyclic 2-alkyl-1,2-diaryl (E)-olefins as selective cyclooxygenase-2 (COX-2) inhibitors. Bioorg. Med. Chem. Lett. 2004 Oct 10/4/2004; 14(19): 4911-4. PMID: 15341950, PII: S0960-894X(04)00919-9, DOI: 10.1016/j.bmcl.2004.07.027, ISSN: 0960-894X.
Rao PN, Uddin MJ, Knaus EE. Design, synthesis, and structure-activity relationship studies of 3,4,6-triphenylpyran-2-ones as selective cyclooxygenase-2 inhibitors. J. Med. Chem. 2004 Jul 7/29/2004; 47(16): 3972-90. PMID: 15267236, DOI: 10.1021/jm049939b, ISSN: 0022-2623.
Uddin MJ, Rao PN, Knaus EE. Design of acyclic triaryl olefins: a new class of potent and selective cyclooxygenase-2 (COX-2) inhibitors. Bioorg. Med. Chem. Lett. 2004 Apr 4/19/2004; 14(8): 1953-6. PMID: 15050635, PII: S0960894X04001556, DOI: 10.1016/j.bmcl.2004.01.075, ISSN: 0960-894X.
Uddin, M. J.; Rao, P. N. P.; Knaus, E. E.. Methylsulfonyl and Hydroxyl Substituents Induce (Z)-Stereocontrol in the McMurry Olefination Reaction. Synlett. 2004; 1513.
Uddin MJ, Rao PN, Knaus EE. Design and synthesis of novel celecoxib analogues as selective cyclooxygenase-2 (COX-2) inhibitors: replacement of the sulfonamide pharmacophore by a sulfonylazide bioisostere. Bioorg. Med. Chem. 2003 Nov 11/17/2003; 11(23): 5273-80. PMID: 14604691, PII: S0968089603005583, ISSN: 0968-0896.
Uddin, M. J.; Rao, P. N. P.; Knaus, E. E. Design, Synthesis and Biological Evaluation of Novel Rofecoxib Analogs as Potential Cyclooxygenase-2 (COX-2) Inhibitors: Replacement of Methylsulfonyl Pharmacophore by a Sulfonylazide Bioisostre. Journal of Heterocyclic Chemistry. 2003; 40: 861.
Uddin, M. J.; Kikuchi, M.; Takedatsu, K.; Arai, K.-I.; Fujimoto, T.; Motoyoshiya, J.; Kakehi, A.; Iriue, R.; Shirai, H.; Yamamoto, I.. Synthesis and Structure of Condensed Heterocycles Derived from Intramolecular 1,3-Dipolar Cycloaddition of Transient and Enantiomerically Pure ?-Allylamino Nitrones and Nitrile Oxides in a High Level of Diastereoselectivity. Synthesis. 2000; 365.
Uddin, M. J.; Fujimoto, T.; Kakehi, A.; Shirai, H.; Yamamoto, I.. Diastereoselective Synthesis of Bridgehead Heterocyclic Spiro Compounds Derived from Tandem Michael Intramolecular 1,3-Dipolar Cycloaddition of Nitrones. Heterocyclic Communications. 2000; 6: 113.
Uddin, M. J.; Shinooka, A.; Fujimoto, T.; Shirai, H.; Yamamoto, I.. Isoxazolidine Based New Chral Auxiliary for Asymmetric Synthesis. Heterocyclic Communications. 2000; 6: 505.