Faculty Appointments
Professor of Chemistry
Professor of Biochemistry
Education
Ph.D., Chemistry, Organic, University of Pennsylvania, Philadelphia, PennsylvaniaB.A., Chemistry, Temple University, Philadelphia, Pennsylvania
Office Address
VU Station B 351822
7332 Stevenson Center
TN
7332 Stevenson Center
TN
Research Description
Chemistry and Biology of DNA Damage -Covalent modification of DNA by electrophiles is generally accepted as the initial event in chemical carcinogenesis. If these modifications are not repaired, they can compromise the fidelity of DNA replication leading to mutations and possibly cancer. To properly study the biological processing of pre-mutagenic DNA lesions, oligonucleotides containing structurally defined carcinogen adducts are required. Our laboratory develops synthetic strategies for the site-specific incorporation of nucleotides that are chemically modified by carcinogens into DNA. Once synthesized, the structure, replication and repair of the carcinogen-modified oligonucleotides are examined. Many of these studies are preformed in collaboration with other laboratories on Vanderbilt's campus and elsewhere.
One specific project includes the preparation of the C8-deoxyguanosine adduct of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ). IQ is a member of a family of highly mutagenic heterocyclic amines found in cooked meats. We found that the C8-IQ adduct adopts different conformations depending on the sequence of the adducted oligonucleotide and we have hypothesized that this sequence-dependent conformation plays an important role in the biological processing of the lesion. This hypothesis will be tested using in vitro and in vivo systems. The adduction of IQ with DNA also gives a minor N2-adduct of deoxyguanosine, which has not been extensively studied. We have recently completed a synthesis of the N2-adduct and have incorporated it into oligonucleotides.
A second major project in our lab involves DNA adducts derived from endogneous sources such as lipid peroxidation. Examples of such reactive electrophiles include alpha,beta-unsaturated aldehydes (acrolein, crotonaldehyde, and 4-hydroxynonenal), 2,3-epoxyaldehydes and dicarbonyl species (malondialdehyde and 4-oxo-2-nonenal). Although these compounds are chemically simple, they react with DNA in a complex and diverse manner. We recently demonstrated that alpha,beta-unsaturated aldehydes can form inter- and intra-strand DNA crosslinks, which are a very severe but largely unstudied form of DNA damage. The crosslinking chemistry is highly dependent on the stereochemistry of the DNA adduct. In collaboration with other laboratories, we are studying the mechanism of the DNA crosslinking reaction and the biological processing of the DNA crosslinks.
Modern mass spectrometry and NMR are integral parts to all of our studies on DNA damage. We have convenient and open access to superb analytical facilities on Vanderbilt campus. Our laboratory is affiliated with the Vanderbilt Center in Molecular Toxicology, Vanderbilt Institute of Chemical Biology, and the Vanderbilt-Ingram Cancer Center .
One specific project includes the preparation of the C8-deoxyguanosine adduct of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ). IQ is a member of a family of highly mutagenic heterocyclic amines found in cooked meats. We found that the C8-IQ adduct adopts different conformations depending on the sequence of the adducted oligonucleotide and we have hypothesized that this sequence-dependent conformation plays an important role in the biological processing of the lesion. This hypothesis will be tested using in vitro and in vivo systems. The adduction of IQ with DNA also gives a minor N2-adduct of deoxyguanosine, which has not been extensively studied. We have recently completed a synthesis of the N2-adduct and have incorporated it into oligonucleotides.
A second major project in our lab involves DNA adducts derived from endogneous sources such as lipid peroxidation. Examples of such reactive electrophiles include alpha,beta-unsaturated aldehydes (acrolein, crotonaldehyde, and 4-hydroxynonenal), 2,3-epoxyaldehydes and dicarbonyl species (malondialdehyde and 4-oxo-2-nonenal). Although these compounds are chemically simple, they react with DNA in a complex and diverse manner. We recently demonstrated that alpha,beta-unsaturated aldehydes can form inter- and intra-strand DNA crosslinks, which are a very severe but largely unstudied form of DNA damage. The crosslinking chemistry is highly dependent on the stereochemistry of the DNA adduct. In collaboration with other laboratories, we are studying the mechanism of the DNA crosslinking reaction and the biological processing of the DNA crosslinks.
Modern mass spectrometry and NMR are integral parts to all of our studies on DNA damage. We have convenient and open access to superb analytical facilities on Vanderbilt campus. Our laboratory is affiliated with the Vanderbilt Center in Molecular Toxicology, Vanderbilt Institute of Chemical Biology, and the Vanderbilt-Ingram Cancer Center .
Research Keywords
DNA Damage, organic synthesis, oligonucleotides, cacinogenesis, DNA repair, DNA replication, translesion synthesis, mutagenesis, chemotherapy
Publications
Cho YJ, Kozekov ID, Harris TM, Rizzo CJ, Stone MP. Stereochemistry modulates the stability of reduced interstrand cross-links arising from R- and S-alpha-CH3-gamma-OH-1,N2-propano-2'-deoxyguanosine in the 5'-CpG-3' DNA sequence. Biochemistry [print-electronic]. 2007 Mar 3/13/2007; 46(10): 2608-21. PMID: 17305317, PMCID: PMC2581467, DOI: 10.1021/bi061381h, ISSN: 0006-2960.
Elmquist CE, Wang F, Stover JS, Stone MP, Rizzo CJ. Conformational differences of the C8-deoxyguanosine adduct of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) within the NarI recognition sequence. Chem. Res. Toxicol [print-electronic]. 2007 Mar; 20(3): 445-54. PMID: 17311423, PMCID: PMC2743555, DOI: 10.1021/tx060229d, ISSN: 0893-228X.
Stover JS, Ciobanu M, Cliffel DE, Rizzo CJ. Chemical and electrochemical oxidation of C8-arylamine adducts of 2'-deoxyguanosine. J. Am. Chem. Soc [print-electronic]. 2007 Feb 2/21/2007; 129(7): 2074-81. PMID: 17256856, PMCID: PMC2526121, DOI: 10.1021/ja066404u, ISSN: 0002-7863.
Stover JS, Chowdhury G, Zang H, Guengerich FP, Rizzo CJ. Translesion synthesis past the C8- and N2-deoxyguanosine adducts of the dietary mutagen 2-Amino-3-methylimidazo[4,5-f]quinoline in the NarI recognition sequence by prokaryotic DNA polymerases. Chem. Res. Toxicol. 2006 Nov; 19(11): 1506-17. PMID: 17112239, PMCID: PMC3150502, DOI: 10.1021/tx0601455, ISSN: 0893-228X.
Wang H, Kozekov ID, Kozekova A, Tamura PJ, Marnett LJ, Harris TM, Rizzo CJ. Site-specific synthesis of oligonucleotides containing malondialdehyde adducts of deoxyguanosine and deoxyadenosine via a postsynthetic modification strategy. Chem. Res. Toxicol. 2006 Nov; 19(11): 1467-74. PMID: 17112234, PMCID: PMC2441645, DOI: 10.1021/tx060137o, ISSN: 0893-228X.
Choi JY, Stover JS, Angel KC, Chowdhury G, Rizzo CJ, Guengerich FP. Biochemical basis of genotoxicity of heterocyclic arylamine food mutagens: Human DNA polymerase eta selectively produces a two-base deletion in copying the N2-guanyl adduct of 2-amino-3-methylimidazo[4,5-f]quinoline but not the C8 adduct at the NarI G3 site. J. Biol. Chem [print-electronic]. 2006 Sep 9/1/2006; 281(35): 25297-306. PMID: 16835218, PII: M605699200, DOI: 10.1074/jbc.M605699200, ISSN: 0021-9258.
Wang F, DeMuro NE, Elmquist CE, Stover JS, Rizzo CJ, Stone MP. Base-displaced intercalated structure of the food mutagen 2-amino-3-methylimidazo[4,5-f]quinoline in the recognition sequence of the NarI restriction enzyme, a hotspot for -2 bp deletions. J. Am. Chem. Soc. 2006 Aug 8/9/2006; 128(31): 10085-95. PMID: 16881637, PMCID: PMC2692337, DOI: 10.1021/ja062004v, ISSN: 0002-7863.
Cho YJ, Wang H, Kozekov ID, Kozekova A, Kurtz AJ, Jacob J, Voehler M, Smith J, Harris TM, Rizzo CJ, Lloyd RS, Stone MP. Orientation of the crotonaldehyde-derived N2-[3-Oxo-1(S)-methyl-propyl]-dG DNA adduct hinders interstrand cross-link formation in the 5'-CpG-3' sequence. Chem. Res. Toxicol. 2006 Aug; 19(8): 1019-29. PMID: 16918240, DOI: 10.1021/tx0600604, ISSN: 0893-228X.
Choi JY, Zang H, Angel KC, Kozekov ID, Goodenough AK, Rizzo CJ, Guengerich FP. Translesion synthesis across 1,N2-ethenoguanine by human DNA polymerases. Chem. Res. Toxicol. 2006 Jun; 19(6): 879-86. PMID: 16780368, PMCID: PMC3130186, DOI: 10.1021/tx060051v, ISSN: 0893-228X.
Otteneder MB, Knutson CG, Daniels JS, Hashim M, Crews BC, Remmel RP, Wang H, Rizzo C, Marnett LJ. In vivo oxidative metabolism of a major peroxidation-derived DNA adduct, M1dG. Proc. Natl. Acad. Sci. U.S.A [print-electronic]. 2006 Apr 4/25/2006; 103(17): 6665-9. PMID: 16614064, PMCID: PMC1458938, PII: 0602017103, DOI: 10.1073/pnas.0602017103, ISSN: 0027-8424.
Cho YJ, Wang H, Kozekov ID, Kurtz AJ, Jacob J, Voehler M, Smith J, Harris TM, Lloyd RS, Rizzo CJ, Stone MP. Stereospecific formation of interstrand carbinolamine DNA cross-links by crotonaldehyde- and acetaldehyde-derived alpha-CH3-gamma-OH-1,N2-propano-2'-deoxyguanosine adducts in the 5'-CpG-3' sequence. Chem. Res. Toxicol. 2006 Feb; 19(2): 195-208. PMID: 16485895, PMCID: PMC2631444, DOI: 10.1021/tx050239z, ISSN: 0893-228X.
Cho YJ, Kim HY, Huang H, Slutsky A, Minko IG, Wang H, Nechev LV, Kozekov ID, Kozekova A, Tamura P, Jacob J, Voehler M, Harris TM, Lloyd RS, Rizzo CJ, Stone MP. Spectroscopic characterization of interstrand carbinolamine cross-links formed in the 5'-CpG-3' sequence by the acrolein-derived gamma-OH-1,N2-propano-2'-deoxyguanosine DNA adduct. J. Am. Chem. Soc. 2005 Dec 12/21/2005; 127(50): 17686-96. PMID: 16351098, PMCID: PMC2631571, DOI: 10.1021/ja053897e, ISSN: 0002-7863.
Goodenough AK, Kozekov ID, Zang H, Choi JY, Guengerich FP, Harris TM, Rizzo CJ. Site specific synthesis and polymerase bypass of oligonucleotides containing a 6-hydroxy-3,5,6,7-tetrahydro-9H-imidazo[1,2-a]purin-9-one base, an intermediate in the formation of 1,N2-etheno-2'-deoxyguanosine. Chem. Res. Toxicol. 2005 Nov; 18(11): 1701-14. PMID: 16300379, PMCID: PMC3135970, DOI: 10.1021/tx050141k, ISSN: 0893-228X.
Zang H, Goodenough AK, Choi JY, Irimia A, Loukachevitch LV, Kozekov ID, Angel KC, Rizzo CJ, Egli M, Guengerich FP. DNA adduct bypass polymerization by Sulfolobus solfataricus DNA polymerase Dpo4: analysis and crystal structures of multiple base pair substitution and frameshift products with the adduct 1,N2-ethenoguanine. J. Biol. Chem [print-electronic]. 2005 Aug 8/19/2005; 280(33): 29750-64. PMID: 15965231, PII: M504756200, DOI: 10.1074/jbc.M504756200, ISSN: 0021-9258.
Scholdberg TA, Merritt WK, Dean SM, Kowalcyzk A, Harris CM, Harris TM, Rizzo CJ, Lloyd RS, Stone MP. Structure of an oligodeoxynucleotide containing a butadiene oxide-derived N1 beta-hydroxyalkyl deoxyinosine adduct in the human N-ras codon 61 sequence. Biochemistry. 2005 Mar 3/8/2005; 44(9): 3327-37. PMID: 15736943, DOI: 10.1021/bi0482452, ISSN: 0006-2960.
Stover JS, Rizzo CJ. Synthesis of the N2-deoxyguanosine adduct of the potent dietary mutagen IQ. Org. Lett. 2004 Dec 12/23/2004; 6(26): 4985-8. PMID: 15606116, DOI: 10.1021/ol047851m, ISSN: 1523-7060.
Elmquist CE, Stover JS, Wang Z, Rizzo CJ. Site-specific synthesis and properties of oligonucleotides containing C8-deoxyguanosine adducts of the dietary mutagen IQ. J. Am. Chem. Soc. 2004 Sep 9/15/2004; 126(36): 11189-201. PMID: 15355100, DOI: 10.1021/ja0487022, ISSN: 0002-7863.
Brock AK, Kozekov ID, Rizzo CJ, Harris TM. Coupling products of nucleosides with the glyoxal adduct of deoxyguanosine. Chem. Res. Toxicol. 2004 Aug; 17(8): 1047-56. PMID: 15310236, DOI: 10.1021/tx049906z, ISSN: 0893-228X.
West JD, Ji C, Duncan ST, Amarnath V, Schneider C, Rizzo CJ, Brash AR, Marnett LJ. Induction of apoptosis in colorectal carcinoma cells treated with 4-hydroxy-2-nonenal and structurally related aldehydic products of lipid peroxidation. Chem. Res. Toxicol. 2004 Apr; 17(4): 453-62. PMID: 15089087, DOI: 10.1021/tx034248o, ISSN: 0893-228X.
Wang H, Marnett LJ, Harris TM, Rizzo CJ. A novel synthesis of malondialdehyde adducts of deoxyguanosine, deoxyadenosine, and deoxycytidine. Chem. Res. Toxicol. 2004 Feb; 17(2): 144-9. PMID: 14967001, DOI: 10.1021/tx034174g, ISSN: 0893-228X.
Wang H, Kozekov ID, Harris TM, Rizzo CJ. Site-specific synthesis and reactivity of oligonucleotides containing stereochemically defined 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal. J. Am. Chem. Soc. 2003 May 5/14/2003; 125(19): 5687-700. PMID: 12733907, DOI: 10.1021/ja0288800, ISSN: 0002-7863.
Kozekov ID, Nechev LV, Moseley MS, Harris CM, Rizzo CJ, Stone MP, Harris TM. DNA interchain cross-links formed by acrolein and crotonaldehyde. J. Am. Chem. Soc. 2003 Jan 1/8/2003; 125(1): 50-61. PMID: 12515506, DOI: 10.1021/ja020778f, ISSN: 0002-7863.
Nechev LV, Kozekov ID, Brock AK, Rizzo CJ, Harris TM. DNA adducts of acrolein: site-specific synthesis of an oligodeoxynucleotide containing 6-hydroxy-5,6,7,8-tetrahydropyrimido[1,2-a]purin-10(3H)-one, an acrolein adduct of guanine. Chem. Res. Toxicol. 2002 May; 15(5): 607-13. PMID: 12018980, PII: tx010181y, ISSN: 0893-228X.
Guo F, Chang BH, Rizzo CJ. An N1-hydrogen bonding model for flavin coenzyme. Bioorg. Med. Chem. Lett. 2002 Jan 1/21/2002; 12(2): 151-4. PMID: 11755342, PII: S0960894X01007120, ISSN: 0960-894X.
Wang H, Rizzo CJ. Stereocontrolled syntheses of all four stereoisomeric 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal. Org. Lett. 2001 Nov 11/1/2001; 3(22): 3603-5. PMID: 11678719, PII: ol016810c, ISSN: 1523-7060.
Rizzo CJ. Further computational studies on the conformation of 1,5-dihydrolumiflavin. Antioxid. Redox Signal. 2001 Oct; 3(5): 737-46. PMID: 11761324, DOI: 10.1089/15230860152664948, ISSN: 1523-0864.
Wang F, Wang H, Polavarapu PL, Rizzo CJ. Absolute configuration and conformational stability of (+)-2,5-dimethylthiolane and (-)-2,5-dimethylsulfolane. J. Org. Chem. 2001 May 5/18/2001; 66(10): 3507-12. PMID: 11348137, PII: jo0100401, ISSN: 0022-3263.
Wang Z, Rizzo CJ. Synthesis of the C8-deoxyguanosine adduct of the food mutagen IQ. Org. Lett. 2001 Feb 2/22/2001; 3(4): 565-8. PMID: 11178826, PII: ol006968h, ISSN: 1523-7060.
Wang Z, Prudhomme DR, Buck JR, Park M, Rizzo CJ. Stereocontrolled syntheses of deoxyribonucleosides via photoinduced electron-transfer deoxygenation of benzoyl-protected ribo- and arabinonucleosides. J. Org. Chem. 2000 Sep 9/22/2000; 65(19): 5969-85. PMID: 10987930, PII: jo0003652, ISSN: 0022-3263.
Reibenspies JH, Guo F, Rizzo CJ. X-ray crystal structures of conformationally biased flavin models. Org. Lett. 2000 Apr 4/6/2000; 2(7): 903-6. PMID: 10768182, ISSN: 1523-7060.
Wang Z, Rizzo CJ. Regioselective synthesis of beta-N1- and beta-N3-alloxazine nucleosides. Org. Lett. 2000 Jan 1/27/2000; 2(2): 227-30. PMID: 10814288, PII: ol9913338, ISSN: 1523-7052.
Hasford, JJ, Rizzo, CJ. A Linear Free Energy Substituent Effect on Flavin Redox Chemistry. J. Am. Chem. Soc. 1998; 120((10)): 2251-55.
Prudhomme DR, Wang Z, Rizzo CJ. An Improved Photosensitizer for the Photoinduced Electron-Transfer Deoxygenation of Benzoates and m-(Trifluoromethyl)benzoates. J. Org. Chem. 1997 Nov 11/14/1997; 62(23): 8257-60. PMID: 11671949, ISSN: 1520-6904.
Hasford, JJ, Kemnitzer, W,Rizzo, CJ. Conformational Effects on Flavin Redox Chemistry. J. Org. Chem. 1997; 62((16)): 5244-5.
Park M, Rizzo CJ. Stereocontrolled de Novo Synthesis of beta-2'-Deoxyribonucleosides. J. Org. Chem. 1996 Sep 9/6/1996; 61(18): 6092-3. PMID: 11667437, ISSN: 1520-6904.
Minnie Park and Carmelo J. Rizzo. Stereocontrolled, De Novo Synthesis of beta-2'-Deoxyribonucleosides. J. Org. Chem. 1996; 61: 6092-3.
Elmquist CE, Wang F, Stover JS, Stone MP, Rizzo CJ. Conformational differences of the C8-deoxyguanosine adduct of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) within the NarI recognition sequence. Chem. Res. Toxicol [print-electronic]. 2007 Mar; 20(3): 445-54. PMID: 17311423, PMCID: PMC2743555, DOI: 10.1021/tx060229d, ISSN: 0893-228X.
Stover JS, Ciobanu M, Cliffel DE, Rizzo CJ. Chemical and electrochemical oxidation of C8-arylamine adducts of 2'-deoxyguanosine. J. Am. Chem. Soc [print-electronic]. 2007 Feb 2/21/2007; 129(7): 2074-81. PMID: 17256856, PMCID: PMC2526121, DOI: 10.1021/ja066404u, ISSN: 0002-7863.
Stover JS, Chowdhury G, Zang H, Guengerich FP, Rizzo CJ. Translesion synthesis past the C8- and N2-deoxyguanosine adducts of the dietary mutagen 2-Amino-3-methylimidazo[4,5-f]quinoline in the NarI recognition sequence by prokaryotic DNA polymerases. Chem. Res. Toxicol. 2006 Nov; 19(11): 1506-17. PMID: 17112239, PMCID: PMC3150502, DOI: 10.1021/tx0601455, ISSN: 0893-228X.
Wang H, Kozekov ID, Kozekova A, Tamura PJ, Marnett LJ, Harris TM, Rizzo CJ. Site-specific synthesis of oligonucleotides containing malondialdehyde adducts of deoxyguanosine and deoxyadenosine via a postsynthetic modification strategy. Chem. Res. Toxicol. 2006 Nov; 19(11): 1467-74. PMID: 17112234, PMCID: PMC2441645, DOI: 10.1021/tx060137o, ISSN: 0893-228X.
Choi JY, Stover JS, Angel KC, Chowdhury G, Rizzo CJ, Guengerich FP. Biochemical basis of genotoxicity of heterocyclic arylamine food mutagens: Human DNA polymerase eta selectively produces a two-base deletion in copying the N2-guanyl adduct of 2-amino-3-methylimidazo[4,5-f]quinoline but not the C8 adduct at the NarI G3 site. J. Biol. Chem [print-electronic]. 2006 Sep 9/1/2006; 281(35): 25297-306. PMID: 16835218, PII: M605699200, DOI: 10.1074/jbc.M605699200, ISSN: 0021-9258.
Wang F, DeMuro NE, Elmquist CE, Stover JS, Rizzo CJ, Stone MP. Base-displaced intercalated structure of the food mutagen 2-amino-3-methylimidazo[4,5-f]quinoline in the recognition sequence of the NarI restriction enzyme, a hotspot for -2 bp deletions. J. Am. Chem. Soc. 2006 Aug 8/9/2006; 128(31): 10085-95. PMID: 16881637, PMCID: PMC2692337, DOI: 10.1021/ja062004v, ISSN: 0002-7863.
Cho YJ, Wang H, Kozekov ID, Kozekova A, Kurtz AJ, Jacob J, Voehler M, Smith J, Harris TM, Rizzo CJ, Lloyd RS, Stone MP. Orientation of the crotonaldehyde-derived N2-[3-Oxo-1(S)-methyl-propyl]-dG DNA adduct hinders interstrand cross-link formation in the 5'-CpG-3' sequence. Chem. Res. Toxicol. 2006 Aug; 19(8): 1019-29. PMID: 16918240, DOI: 10.1021/tx0600604, ISSN: 0893-228X.
Choi JY, Zang H, Angel KC, Kozekov ID, Goodenough AK, Rizzo CJ, Guengerich FP. Translesion synthesis across 1,N2-ethenoguanine by human DNA polymerases. Chem. Res. Toxicol. 2006 Jun; 19(6): 879-86. PMID: 16780368, PMCID: PMC3130186, DOI: 10.1021/tx060051v, ISSN: 0893-228X.
Otteneder MB, Knutson CG, Daniels JS, Hashim M, Crews BC, Remmel RP, Wang H, Rizzo C, Marnett LJ. In vivo oxidative metabolism of a major peroxidation-derived DNA adduct, M1dG. Proc. Natl. Acad. Sci. U.S.A [print-electronic]. 2006 Apr 4/25/2006; 103(17): 6665-9. PMID: 16614064, PMCID: PMC1458938, PII: 0602017103, DOI: 10.1073/pnas.0602017103, ISSN: 0027-8424.
Cho YJ, Wang H, Kozekov ID, Kurtz AJ, Jacob J, Voehler M, Smith J, Harris TM, Lloyd RS, Rizzo CJ, Stone MP. Stereospecific formation of interstrand carbinolamine DNA cross-links by crotonaldehyde- and acetaldehyde-derived alpha-CH3-gamma-OH-1,N2-propano-2'-deoxyguanosine adducts in the 5'-CpG-3' sequence. Chem. Res. Toxicol. 2006 Feb; 19(2): 195-208. PMID: 16485895, PMCID: PMC2631444, DOI: 10.1021/tx050239z, ISSN: 0893-228X.
Cho YJ, Kim HY, Huang H, Slutsky A, Minko IG, Wang H, Nechev LV, Kozekov ID, Kozekova A, Tamura P, Jacob J, Voehler M, Harris TM, Lloyd RS, Rizzo CJ, Stone MP. Spectroscopic characterization of interstrand carbinolamine cross-links formed in the 5'-CpG-3' sequence by the acrolein-derived gamma-OH-1,N2-propano-2'-deoxyguanosine DNA adduct. J. Am. Chem. Soc. 2005 Dec 12/21/2005; 127(50): 17686-96. PMID: 16351098, PMCID: PMC2631571, DOI: 10.1021/ja053897e, ISSN: 0002-7863.
Goodenough AK, Kozekov ID, Zang H, Choi JY, Guengerich FP, Harris TM, Rizzo CJ. Site specific synthesis and polymerase bypass of oligonucleotides containing a 6-hydroxy-3,5,6,7-tetrahydro-9H-imidazo[1,2-a]purin-9-one base, an intermediate in the formation of 1,N2-etheno-2'-deoxyguanosine. Chem. Res. Toxicol. 2005 Nov; 18(11): 1701-14. PMID: 16300379, PMCID: PMC3135970, DOI: 10.1021/tx050141k, ISSN: 0893-228X.
Zang H, Goodenough AK, Choi JY, Irimia A, Loukachevitch LV, Kozekov ID, Angel KC, Rizzo CJ, Egli M, Guengerich FP. DNA adduct bypass polymerization by Sulfolobus solfataricus DNA polymerase Dpo4: analysis and crystal structures of multiple base pair substitution and frameshift products with the adduct 1,N2-ethenoguanine. J. Biol. Chem [print-electronic]. 2005 Aug 8/19/2005; 280(33): 29750-64. PMID: 15965231, PII: M504756200, DOI: 10.1074/jbc.M504756200, ISSN: 0021-9258.
Scholdberg TA, Merritt WK, Dean SM, Kowalcyzk A, Harris CM, Harris TM, Rizzo CJ, Lloyd RS, Stone MP. Structure of an oligodeoxynucleotide containing a butadiene oxide-derived N1 beta-hydroxyalkyl deoxyinosine adduct in the human N-ras codon 61 sequence. Biochemistry. 2005 Mar 3/8/2005; 44(9): 3327-37. PMID: 15736943, DOI: 10.1021/bi0482452, ISSN: 0006-2960.
Stover JS, Rizzo CJ. Synthesis of the N2-deoxyguanosine adduct of the potent dietary mutagen IQ. Org. Lett. 2004 Dec 12/23/2004; 6(26): 4985-8. PMID: 15606116, DOI: 10.1021/ol047851m, ISSN: 1523-7060.
Elmquist CE, Stover JS, Wang Z, Rizzo CJ. Site-specific synthesis and properties of oligonucleotides containing C8-deoxyguanosine adducts of the dietary mutagen IQ. J. Am. Chem. Soc. 2004 Sep 9/15/2004; 126(36): 11189-201. PMID: 15355100, DOI: 10.1021/ja0487022, ISSN: 0002-7863.
Brock AK, Kozekov ID, Rizzo CJ, Harris TM. Coupling products of nucleosides with the glyoxal adduct of deoxyguanosine. Chem. Res. Toxicol. 2004 Aug; 17(8): 1047-56. PMID: 15310236, DOI: 10.1021/tx049906z, ISSN: 0893-228X.
West JD, Ji C, Duncan ST, Amarnath V, Schneider C, Rizzo CJ, Brash AR, Marnett LJ. Induction of apoptosis in colorectal carcinoma cells treated with 4-hydroxy-2-nonenal and structurally related aldehydic products of lipid peroxidation. Chem. Res. Toxicol. 2004 Apr; 17(4): 453-62. PMID: 15089087, DOI: 10.1021/tx034248o, ISSN: 0893-228X.
Wang H, Marnett LJ, Harris TM, Rizzo CJ. A novel synthesis of malondialdehyde adducts of deoxyguanosine, deoxyadenosine, and deoxycytidine. Chem. Res. Toxicol. 2004 Feb; 17(2): 144-9. PMID: 14967001, DOI: 10.1021/tx034174g, ISSN: 0893-228X.
Wang H, Kozekov ID, Harris TM, Rizzo CJ. Site-specific synthesis and reactivity of oligonucleotides containing stereochemically defined 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal. J. Am. Chem. Soc. 2003 May 5/14/2003; 125(19): 5687-700. PMID: 12733907, DOI: 10.1021/ja0288800, ISSN: 0002-7863.
Kozekov ID, Nechev LV, Moseley MS, Harris CM, Rizzo CJ, Stone MP, Harris TM. DNA interchain cross-links formed by acrolein and crotonaldehyde. J. Am. Chem. Soc. 2003 Jan 1/8/2003; 125(1): 50-61. PMID: 12515506, DOI: 10.1021/ja020778f, ISSN: 0002-7863.
Nechev LV, Kozekov ID, Brock AK, Rizzo CJ, Harris TM. DNA adducts of acrolein: site-specific synthesis of an oligodeoxynucleotide containing 6-hydroxy-5,6,7,8-tetrahydropyrimido[1,2-a]purin-10(3H)-one, an acrolein adduct of guanine. Chem. Res. Toxicol. 2002 May; 15(5): 607-13. PMID: 12018980, PII: tx010181y, ISSN: 0893-228X.
Guo F, Chang BH, Rizzo CJ. An N1-hydrogen bonding model for flavin coenzyme. Bioorg. Med. Chem. Lett. 2002 Jan 1/21/2002; 12(2): 151-4. PMID: 11755342, PII: S0960894X01007120, ISSN: 0960-894X.
Wang H, Rizzo CJ. Stereocontrolled syntheses of all four stereoisomeric 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal. Org. Lett. 2001 Nov 11/1/2001; 3(22): 3603-5. PMID: 11678719, PII: ol016810c, ISSN: 1523-7060.
Rizzo CJ. Further computational studies on the conformation of 1,5-dihydrolumiflavin. Antioxid. Redox Signal. 2001 Oct; 3(5): 737-46. PMID: 11761324, DOI: 10.1089/15230860152664948, ISSN: 1523-0864.
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Wang Z, Rizzo CJ. Synthesis of the C8-deoxyguanosine adduct of the food mutagen IQ. Org. Lett. 2001 Feb 2/22/2001; 3(4): 565-8. PMID: 11178826, PII: ol006968h, ISSN: 1523-7060.
Wang Z, Prudhomme DR, Buck JR, Park M, Rizzo CJ. Stereocontrolled syntheses of deoxyribonucleosides via photoinduced electron-transfer deoxygenation of benzoyl-protected ribo- and arabinonucleosides. J. Org. Chem. 2000 Sep 9/22/2000; 65(19): 5969-85. PMID: 10987930, PII: jo0003652, ISSN: 0022-3263.
Reibenspies JH, Guo F, Rizzo CJ. X-ray crystal structures of conformationally biased flavin models. Org. Lett. 2000 Apr 4/6/2000; 2(7): 903-6. PMID: 10768182, ISSN: 1523-7060.
Wang Z, Rizzo CJ. Regioselective synthesis of beta-N1- and beta-N3-alloxazine nucleosides. Org. Lett. 2000 Jan 1/27/2000; 2(2): 227-30. PMID: 10814288, PII: ol9913338, ISSN: 1523-7052.
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Prudhomme DR, Wang Z, Rizzo CJ. An Improved Photosensitizer for the Photoinduced Electron-Transfer Deoxygenation of Benzoates and m-(Trifluoromethyl)benzoates. J. Org. Chem. 1997 Nov 11/14/1997; 62(23): 8257-60. PMID: 11671949, ISSN: 1520-6904.
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Minnie Park and Carmelo J. Rizzo. Stereocontrolled, De Novo Synthesis of beta-2'-Deoxyribonucleosides. J. Org. Chem. 1996; 61: 6092-3.
Available Postdoctoral Position Details
Posted: 3/9/2007
Synthesis of oligonucleotides that are covalently modified by carcinogens for structural and biological studies.
Synthesis of oligonucleotides that are covalently modified by carcinogens for structural and biological studies.