Rizzo lab

Publications

Publications

2013

(110) Shell, S. M.; Hawkins, E. K.; Tsai, M.-S.; Rizzo, C. J.; Chazin, W. J. (2013) Xeroderma pigmentosum complementation group C protein (XPC) serves as a general sensor of damaged DNA, DNA Repair, 12 (accepted)

(109) Shanmugam, G., Minko, I. G., Banerjee, S., Christov, P. P., Kozekov, I. D., Rizzo, C. J., Lloyd, R. S., Egli, M., and Stone, M. P. (2013) Ring-Opening of the γ-OH-PdG Adduct Promotes Error-Free Bypass by the Sulfolobus solfataricus DNA polymerase Dpo4, Chem. Res. Toxicol. 26, 1348-1360. PMID: 23947567

(108) Christov, P. P., Hawkins, E. H., Kett, N. R., Rizzo, C. J. (2013) Simplified synthesis of individual stereoisomers of the 4-hydroxynonenal adducts of deoxyguanosine, Tetrahedron Lett. 54, 4289-4291. PMID: 23935223

(107) Earley, L., Minko, I. G., Christov, P. P., Rizzo, C. J., Lloyd, R. S. (2013) “Mutagenic Spectra Arising from Replication Bypass of the 2,6-diamino-4-hydroxy-N5-methyl Formamidopyrimidine Adduct in Primate Cells,” Chem. Res. Toxicol. 26, 1108-1114. PMID: 23763662

2012

(106) Zhao, L., Pence, M. G., Christov, P. P., Wawrzak, Z., Choi, J.-Y., Rizzo, C. J., Egli, M., Guengerich, F. P. (2012) Basis of Miscoding of the DNA Adduct N2,3-Ethenoguanine by Human Y-family DNA Polymerases. J. Biol. Chem. 287, 35516-35526. PMCID: PMC3471744

(105) Christov, P. P., Yamanaka, K., Choi, J.-Y., Takata, K.-I., Wood, R. D., Guengerich, F. P., Lloyd, R. S., Rizzo, C. J. (2012) Replication of the 2,6-Diamino-4-hydroxy-N5-(methyl)-formamidopyrimidine (MeFapy-dGuo) Adduct by Eukaryotic DNA Polymerases. Chem. Res.Toxicol. 25, 1652-61. PMCID: PMC3682502

(104) Zhao, L., Christov, P. P., Kozekov, I. D., Pence, M. G., Pallan, P. P., Rizzo, C. J., Egli,M., and Guengerich, F. P. (2012) Replication of N2,3-Ethenoguanine by DNA Polymerases. Angew. Chem. Int. Ed. Eng., 51, 5466-5469. PMCID: PMC3671877

(103) Banerjee, S., Christov, P. P., Kozekova, A., Rizzo, C. J., Egli, M., and Stone, M. P. (2012) Replication Bypass of the trans-4-hydroxynonenal-derived (6S,8R,11S) 1,N2-deoxyguanosine DNA adducts by the Sulfolobus solfataricus DNA polymerase IV. Chem. Res. Toxicol., 25, 422-435. PMCID: PMC3285121

2011

(102) Harris, C. M., Stec, D. F., Christov, P. P., Kozekov, I. D., Rizzo, C. J., Harris, T. M., (2011) Deoxyguanosine Forms a Bis-adduct with E,E-Muconaldehyde, an Oxidative Metabolite of Benzene. Implications for the Carcinogenicity of Benzene. Chem. Res. Toxicol., 24, 1994-1956. PMCID: PMC3408037

(101) Huang, H., Wang, H., Kozekova, A., Rizzo, C. J., Stone, M. P. (2011) Formation of a N2-dG:N2-dG carbinolamine DNA cross-link by a trans-4-hydroxynonenal-derived (6S,8R,11S) 1,N2-dG adduct. J. Am. Chem. Soc., 133, 16101-16110. PMCID: PMC3187658

(100) Huang, H., Wang, H., Voehler, M. W., Kozekova, A., Rizzo, C. J., McCullough, A. K., Lloyd, R. S., Stone, M. P. (2011) γ-Hydroxy-1,N2-propano-2’-deoxyguanosine DNA adduct conjugates the N-terminal amine of the KWKK peptide via a  carbinolamine linkage. Chem. Res.Toxicol., 24, 1123-1133. PMCID: PMC3138414

(99) Shanmugam, G., Kozekov, I. D., Guengerich, F. P., Rizzo, C. J., Stone, M. P. (2011) 1,N2-Etheno-2'-deoxyguanosine adopts the syn conformation about the glycosyl bond when mismatched with deoxyadenosine. Chem. Res. Toxicol., 24, 1071-1079. PMCID: PMC3138413

(98) Polavarapu, P. L., Donahue, E. A., Shanmugam, G., Scalmani, G., Hawkins, E. K., Rizzo, C., Ibnusaud, I., Thomas, G., Habal, D., Sebastian, D. (2011) A single chiroptical spectroscopic method may not be able to establish the absolute configurations of diastereomers: Dimethylesters of hibiscus and garcinia acids. J. Phys. Chem. A, 115, 5665-5673. PMCID: PMC3702036

(97) Petrova, K. V., Stec, D, F., Voehler, M. W., Rizzo, C. J. (2011) Synthesis of the four stereoisomers of 2,3-epoxy-4-hydroxynonanal and their reactivity with deoxyguanosine. Org. Biomol. Chem., 9, 1960-1971. PMCID: PMC3694406

(96) Polavarapu, P. L., Scalmani, G., Hawkins, E. K., Rizzo, C., Jeirath, N., Ibnusaud, I., Habal, D., Nair, D. S., Haleema, S., (2011) Importance of solvation in understanding the chiroptical spectra of natural products in solution phase: Garcinia acid dimethyl ester. J. Nat. Prod. 74, 321-328. PMCID: PMC3699186

2010

(95) Kozekov, I. D.,Turesky, R. J.; Alas, G. R., Harris, C. M.; Harris, T. M., Rizzo. C. J. (2010) Formation of deoxyguanosine cross-links from calf thymus DNA treated with acrolein and 4-hydroxy-2-nonenal. Chem. Res. Toxicol. 23, 1701-1713. PMCID: PMC2990652

(94) Maddukuri, L., Eoff, R. L., Choi, J. Y., Rizzo, C. J., Guengerich, F. P., Marnett, L.J. (2010) In vitro bypass of the major malondialdehyde- and base propenal-derived DNA adduct by human Y-family DNA polymerases κ, ι, and Rev1, Biochemistry 49, 8415-8424. PMCID: PMC2943251

(93) Christov, P. P., Banerjee, S., Stone, M. P. and Rizzo, C. J. (2010) Selective incision of the α-N5-methyl formamidopyrimidine anomer by Escherichia coli Endonuclease IV, J. Nucleic Acids, 2010, Article ID 850234, doi:10.4061/2010/850234.  PMCID: PMC2925382

(92) Huang, H., Kozekov, I. D., Kozekova, A. Rizzo, C. J., McCullough, A. K., Lloyd, R. S. and Stone, M. P. (2010) Minor groove orientation of the KWKK peptide tethered via the N-terminal amine to the acrolein-derived 1,N2-γ-hydroxy-propanodeoxyguanosine lesion with a trimethylene linkage, Biochemistry 49, 6155–6164. PMCID: PMC2907095

(91) Huang, H., Kozekov, I. D., Kozekova, A. Wang, H., Lloyd, R. S., Rizzo, C. J. and Stone, M. P. (2010) DNA cross-links induced by trans-4-hydroxynonenal. Environ. Mol. Mutagen. 51, 625-634. PMCID: PMC3140422

(90) Christov, P. P., Petrova, K. V., Shanmugam, G., Kozekov, Kozekova, A., Guengerich, F. P., Stone, M. P., Rizzo, C. J. (2010) Comparison of the in vitro replication of the 7-(2-oxoheptyl)-1,N2-etheno-2'-deoxyguanosine and 1,N2-etheno-2'-deoxyguanosine lesions by Sulfolobus solfataricus P2 DNA polymerase IV (Dpo4). Chem. Res. Toxicol. 23, 1330-1341. PMCID: PMC2922457

(89) Christov, P. P., Chowdhury, G., Garmendia, C. A., Wang, F., Stover, J. S., Elmquist, C. E., Kozekova, A., Angel, K. C., Turesky, R. J., Stone, M. P., Guengerich, F. P., Rizzo, C. J. (2010) The C8-2'-deoxyguanosine adduct of 2-amino-3-methylimidazo[1,2-d]naphthalene, a carbocyclic analogue of the potent mutagen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), is a block to replication in vitro. Chem. Res.Toxicol., 23, 1076-1088. PMCID: PMC2891123

(88) Shanmugam, G., Kozekov, I. D., Guengerich, F. P., Rizzo, C. J. and Stone, M. P. (2010) Structure of the 1,N2-etheno-2'-deoxyguanosine lesion in the 3'-G(1,N2-εdG)T-5' sequence opposite a one-base deletion. Biochemistry, 2010, 49, 2615-2626. PMCID: PMC2844103

(87) Liu, M., Bandaru, V., Bond, J. P., Jaruga, P., Zhao, X., Christov, P. P., Burrows, C. J., Rizzo, C. J., Dizdaroglu, M. and Wallace, S. S. (2010) The mouse ortholog of NEIL3 is a functional DNA glycosylase in vitro and in vivo. Proc. Natl. Acad. Sci. U.S.A. 107, 4925-4930. PMCID: PMC2841873

(86) Yamanaka, K., Minko, I. G., Takata, K.-i., Kolbanovskiy, A., Kozekov, I. D., Wood, R. D., Rizzo, C. J. and Lloyd, R. S. (2010) Novel enzymatic function of DNA polymerase ν in translesion DNA synthesis past major groove DNA-peptide and DNA-DNA cross-links. Chem. Res. Toxicol.23, 689-695. PMCID: PMC2838406

2009

(85) Wang, L. C., Ben-Yehoyada, M., Kozekov, I. D., Rizzo, C. J., Gottesman, M. E. and Gautier, J. (2009) Checkpoint signaling from a single DNA interstrand crosslink. Mol. Cell, 2009, 35, 704-715. PMCID: PMC2756577

(84) Zhang, H., Bren, U., Kozekov, I. D., Rizzo, C. J., Stec, D. F. and Guengerich, F. P. (2009) Steric and electrostatic effects at the C2 atom substituent influence replication and miscoding of the DNA deamination product deoxyxanthosine and analogs by DNA polymerases. J. Mol. Biol. 392, 251-269. PMCID: PMC2755575

(83) Eoff, R. L., Stafford, J. B., Szekely, J., Rizzo, C. J., Egli, M., Guengerich, F. P. and Marnett, L. J. (2009) Structural and functional analysis of Sulfolobus solfataricus Y-Family DNA polymerase Dpo4-catalyzed bypass of the malondialdehyde-deoxyguanosine adduct. Biochemistry 48, 7079-7088. PMCID: PMC2717710

(82) Zhang, H., Eoff, R. L., Kozekov, I. D., Rizzo, C. J., Egli, M. and Guengerich, F. P. (2009) Structure-function relationships in miscoding by Sulfolobus solfataricus DNA polymerase Dpo4: Guanine N2,N2-dimethyl substitution produces inactive and miscoding polymerase complexes. J. Biol. Chem. 284, 17687-17699. PMCID: PMC2755575

(81) Huang, H., Kim, H.-Y., Kozekov, I. D., Cho, Y.-J., Wang, H., Kozekova, A., Harris, T. M., Rizzo, C. J. and Stone, M. P. (2009) Stereospecific formation of the (R)-γ-hydroxytrimethylene interstrand N2-dG:N2-dG cross-link arising from the γ-OH-1,N2-propano-2′-deoxyguanosine adduct in the 5′-CpG-3′ DNA sequence. J. Am. Chem. Soc. 131, 8416-8424.PMCID: PMC2753404

(80) Christov, P. P., Angel, K. C., Guengerich, F. P. and Rizzo, C. J. (2009) Replication past the N5-methyl-formamidopyrimidine lesion of deoxyguanosine by DNA polymerases and an improved procedure for sequence analysis of in vitro bypass products by mass spectrometry. Chem. Res. Toxicol.22, 1086-1095. PMCID: PMC2754150

(79) Minko, I. G., Kozekov, I. D., Harris, T. M., Rizzo, C. J., Lloyd, R. S. and Stone, M. P. (2009) Chemistry and biology of DNA containing 1,N2-deoxyguanosine adducts of the α,β-unsaturated aldehydes acrolein, crotonaldehyde, and 4-hydroxynonenal. Chem. Res. Toxicol.22, 759-778. PMCID: PMC2685875

(78) Knutson, C. G., Rubinson, E. H., Akingbade, D., Anderson, C. S., Stec, D. F., Petrova, K. V., Kozekov, I. D., Guengerich, F. P., Rizzo, C. J. and Marnett, L. J. (2009) Oxidation and glycolytic cleavage of etheno and propano DNA base adducts. Biochemistry 48, 800-809. PMCID: PMC2975463

(77) Zhang, H., Eoff, R. L., Kozekov, I. D., Rizzo, C. J., Egli, M. and Guengerich, F. P. (2009) Versatility of Y-family Sulfolobus solfataricus DNA polymerase Dpo4 in translesion synthesis past bulky N2-alkyl guanine adducts. J. Biol. Chem. 284, 3563-3576. PMCID: PMC2636699

(76) Stafford, J. B., Eoff, R. L., Kozekova, A., Rizzo, C. J., Guengerich, F. P. and Marnett, L. J. (2009) Translesion DNA synthesis by human DNA polymerase η on templates containing a pyrimidopurinone deoxyguanosine adduct, 3-(2'-deoxy-β-D-erythro-pentofuranosyl)pyrimido-[1,2-a]purin-10(3H)-one. Biochemistry 48, 471-480. PMCID: PMC2651650

(75) Huang, H., Wang, H., Lloyd, R. S., Rizzo, C. J. and Stone, M. P. (2009) Conformational interconversion of the trans-4-hydroxynonenal-derived (6S,8R,11S) 1,N2-deoxyguanosine adduct when mismatched with deoxyadenosine in DNA. Chem. Res. Toxicol.22, 187-200. PMCID: PMC2645987

2008

(74) Christov, P. P., Brown, K. L., Kozekov, I. D., Stone, M. P., Harris, T. M. and Rizzo, C. J. (2008) Site-specific synthesis and characterization of oligonucleotides containing an N6-(2-deoxy-D-erythro-pentofuranosyl)-2,6-diamino-3,4-dihydro-4-oxo-5-N-methylformamidopyrimidine lesion, the ring-opened product from N7-methylation of deoxyguanosine. Chem. Res. Toxicol.21, 2324-2333. PMCID: PMC2701371

(73) Huang, H., Wang, H., Qi, N., Lloyd, R. S., Rizzo, C. J. and Stone, M. P. (2008) The stereochemistry of trans-4-hydroxynonenal-derived exocyclic 1,N2-2'-deoxyguanosine adducts modulates formation of interstrand cross-links in the 5'-CpG-3' sequence. Biochemistry 47, 11457-11472. PMCID: PMC2646759

(72) Minko, I. D., Yamanaka, K., Kozekov, I. D., Kozekova, A., Indiani, C., O'Donnell, M. E., Jiang, Q., Goodman, M. F., Rizzo, C. J. and Lloyd, R. S. (2008) Replication bypass of the acrolein-mediated deoxyguanine DNA-peptide cross-links by DNA polymerases of the DinB family. Chem. Res. Toxicol.21, 1983-1990. PMCID: PMC2673917

(71) Shanmugam, G., Kozekov, I. D., Guengerich, F. P., Rizzo, C. J. and Stone, M. P. (2008) Structure of the 1,N2-ethenodeoxyguanosine adduct opposite cytosine in duplex DNA: Hoogsteen base pairing at pH 5.2. Chem. Res. Toxicol.21, 1795-1805. PMCID: PMC2646752

(70) Christov, P. P., Kozekov, I. D., Rizzo, C. J. and Harris, T. M. (2008) The formamidopyrimidine derivative of 7-(2-oxoethyl)-2'-deoxyguanosine. Chem. Res. Toxicol.21, 1777-1786. PMCID: PMC3138534

(69) Huang, H., Wang, H., Qi, N., Kozekova, A., Rizzo, C. J. and Stone, M. P. (2008) Rearrangement of the (6S,8R,11S) and (6R,8S,11R) exocyclic 1,N2-deoxyguanosine adducts of trans-4-hydroxynonenal to N2-deoxyguanosine cyclic hemiacetal adducts when placed complementary to cytosine in duplex DNA. J. Am. Chem. Soc. 130, 10898-10906. PMCID: PMC2646763

(68) Dexheimer, T. S., Kozekova, A., Rizzo, C. J., Stone, M. P. and Pommier, Y. (2008) The modulation of topoisomerase I-mediated DNA cleavage and the induction of DNA-topoisomerase I crosslinks by crotonaldehyde-derived DNA adducts. Nucleic Acids Res. 36, 4128-4136. PMCID: PMC2475617

(67) Stone, M. P., Cho, Y.-J., Huang, H., Kim, H.-Y., Kozekov, I. D., Kozekova, A., Wang, H., Minko, I. G., Lloyd, R. S., Harris, T. M. and Rizzo, C. J. (2008) Interstrand DNA cross-links induced by α,β-unsaturated aldehydes derived from lipid peroxidation and environmental sources. Acc. Chem. Res. 41, 793-804. PMCID: PMC2785109

(66) Minko, I. G., Harbut, M. B., Kozekov, I. D., Kozekova, A., Jakobs, P. M., Olson, S. B., Moses, R. E., Harris, T. M., Rizzo, C. J. and Lloyd, R. S. (2008) Role for DNA polymerase κ in the processing of N2-N2-guanine interstrand cross-links. J. Biol. Chem. 283, 17075-17082. PMCID: PMC2427349

(65) Szekely, J., Rizzo, C. J. and Marnett, L. J. (2008) Chemical properties of oxopropenyl adducts of purine and pyrimidine nucleosides and their reactivity toward amino acid cross-link formation. J. Am. Chem. Soc. 130, 2195-2201. PMCID: PMC2708936

(64) Szekely, J., Wang, H., Peplowski, K. M., Knutson, C. G., Marnett, L. J. and Rizzo, C. J. (2008) "One-pot" syntheses of malondialdehyde adducts of nucleosides. Nucleosides Nucleotides & Nucleic Acids 27, 103-109. PMCID: PMC3129002

(63) Minko, I. G., Kozekov, I. D., Kozekova, A., Harris, T. M., Rizzo, C. J. and Lloyd, R. S. (2008) Mutagenic potential of DNA-peptide crosslinks mediated by acrolein-derived DNA adducts. Mutat. Res. 637, 161-172. PMCID: PMC3181171

2007

(62) Stover, J. S. and Rizzo, C. J. (2007) Synthesis of oligonucleotides containing the N2-deoxyguanosine adduct of the dietary carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline. Chem. Res. Toxicol.20, 1972-1979. PMCID: PMC3138521

(61) Knutson, C. G., Wang, H. Rizzo C. J. and Marnett, L. J. (2007) Metabolism and elimination of the endogenous DNA adduct, 3-(2-deoxy-β-D-erythro-pentofuranosyl)-pyrimido[1,2-a]purine-10(3H)-one, in the rat. J. Biol. Chem. 282, 36257-36264. PMID: 17951255

(60) Petrova, K. V., Jalluri, R. S., Kozekov I. D. and Rizzo, C. J.. (2007) Mechanism of 1,N2-etheno-2'-deoxyguanosine formation from epoxyaldehydes. Chem. Res. Toxicol.20, 1685-1692. PMCID: PMC3133930

(59) Shanmugam, G., Goodenough, A. K. Kozekov, I. D., Guengerich, F. P., Rizzo C. J. and Stone, M. P.. (2007) Structure of the 1,N2-etheno-2'-deoxyguanosine adduct in duplex DNA at pH 8.6. Chem. Res. Toxicol. 20, 1601-1611. PMCID: PMC2546360

(58) Wang, F., Elmquist, C. E., Stover, J. S., Rizzo, C. J. and Stone, M. P. (2007) DNA sequence modulates the conformation of the food mutagen 2-amino-3-methylimidazo[4,5-f]quinoline in the recognition sequence of the NarI restriction enzyme. Biochemistry 46, 8498-8516. PMCID: PMC2782574

(57) Cho, Y.-J., Kozekov, I. D., Harris, T. M., Rizzo, C. J. and Stone, M. P. (2007) Stereochemistry modulates the stability of reduced interstrand cross-links arising from R- and S-α-CH3-γ-OH-1,N2-propano-2'-deoxyguanosine in the 5'-CpG-3' DNA sequence. Biochemistry 46, 2608-2621. PMCID: PMC2581467

(56) Elmquist, C. E., Wang, F., Stover, J. S., Stone, M. P. and Rizzo, C. J. (2007) 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.20, 445-454. PMCID: PMC2743555

(55) Stover, J. S., Ciobanu, M., Cliffel, D. E. and Rizzo, C. J. (2007) Chemical and electrochemical oxidation of C8-arylamine adducts of 2'-deoxyguanosine. J. Am. Chem. Soc. 129, 2074-2081. PMCID: PMC2526121

2006

(54) Stover, J. S., Chowdhury, G., Zang, H., Guengerich, F. P. and Rizzo, C. J. (2006) 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.19, 1506-1517. PMCID: PMC3150502

(53) Wang, H., Kozekov, I. D., Kozekova, A., Tamura, P. J., Marnett, L. J., Harris, T. M. and Rizzo, C. J. (2006) Site-specific synthesis of oligonucleotides containing malondialdehyde adducts of deoxyguanosine and deoxyadenosine via a postsynthetic modification strategy. Chem. Res. Toxicol.19, 1467-1474. PMCID: PMC2441645

(52) Choi, J.-Y., Stover, J. S., Angel, K. C., Chowdhury, G., Rizzo, C. J. and Guengerich, F. P. (2006) Biochemical basis of genotoxicity of heterocyclic arylamine food mutagens: Human DNA polymerase h 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. 281, 25297-25306. PMID: 16835218

(51) Cho, Y.-J., Wang, H., Kozekov, I. D., Kozekova, A., Kurtz, A. J., Jacob, J., Voehler, M., Smith, J., Harris, T. M., Rizzo, C. J., Lloyd, R. S. and Stone, M. P. (2006) 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.19, 1019-1029. PMID: 16918240

(50) Wang, F., DeMuro, N. E., Elmquist, C. E., Stover, J. S., Rizzo, C. J. and Stone, M. P. (2006) 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. 128, 10085-10095. PMCID: PMC2692337

(49) Choi, J.-Y., Zang, H., Angel, K. C., Kozekov, I. D., Goodenough, A. K., Rizzo, C. J. and Guengerich, F. P. (2006) Translesion synthesis across 1,N2-ethenoguanine by human DNA polymerases. Chem. Res. Toxicol.19, 879-886. PMCID: PMC3130186

(48) Otteneder, M., Knutson, C., Daniels, J., Hashim, M., Crews, B., Remmel, R., Wang, H., Rizzo, C. and Marnett, L. (2006) In vivo oxidative metabolism of a major peroxidation-derived DNA adduct, M1dG. Proc. Natl. Acad. Sci. U.S.A. 103, 6665-6669. PMCID: PMC1458938

(47) Cho, Y.-J., Wang, H., Kozekov, I. D., Kurtz, A., Jacob, J., Voehler, M., Smith, J., Harris, T. M., Lloyd, R. S., Rizzo, C. J. and Stone, M. P. (2006) Stereospecific formation of interstrand carbinolamine DNA cross-links by crotonaldehyde- and acetaldehyde-derived α-CH3-γ-OH-1,N2-propano-2'-deoxyguanosine adducts in the 5'-CpG-3' sequence. Chem. Res. Toxicol.19, 195-208. PMCID: PMC2631444

2005

(46) Goodenough, A. K., Kozekov, I. D., Zang, H., Choi, J.-Y., Guengerich, F. P., Harris, T. M. and Rizzo, C. J. (2005) 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. 18, 1701-1714. PMCID: PMC3135970

(45) Zang, H., Goodenough, A. K., Choi, J.-Y., Irimia, A., Loukachevitch, L. V., Kozekov, I. D., Angel, K. C., Rizzo, C. J., Egli, M. and Guengerich, F. P. (2005) 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. 280, 29750-29764. PMID: 15965231

(44) Cho, Y.-J., Kim, H., Huang, H., Slutsky, A., Minko, I. G., Wang, H., Nechev, L. V., Kozekov, I. D., Kozekova, A., Tamura, P., Jacob, J., Voehler, M., Harris, T. M., Lloyd, R. S., Rizzo, C. J. and Stone, M. P. (2005) Spectroscopic characterization of interstrand carbinolamine cross-links formed in the 5'-CpG-3' sequence by the acrolein-derived γ-OH-1,N2-propano-2'-deoxyguanosine DNA adduct. J. Am. Chem. Soc. 127, 17686-17696. PMCID: PMC2631571

(43) Scholdberg, T. A., Merritt, W. K., Dean, S. M., Kowalcyzk, A., Harris, C. M., Harris, T. M., Rizzo, C. J., Lloyd, R. S. and Stone, M. P. (2005) Structure of an oligodeoxynucleotide containing a butadiene oxide-derived N1 β-hydroxyalkyl deoxyinosine adduct in the human N-ras codon 61 sequence. Biochemistry 44, 3327-3337. PMID: 15736943

2004

(42) Stover, J. S. and Rizzo, C. J. (2004) Synthesis of the N2-deoxyguanosine adduct of the potent dietary mutagen IQ. Org. Lett. 6, 4985-4988. PMID: 15606116

(41) Elmquist, C. E., Stover, J. S., Wang, Z. and Rizzo, C. J. (2004) Site-specific synthesis and properties of oligonucleotides containing C8-deoxyguanosine adducts of the dietary mutagen IQ. J. Am. Chem. Soc. 126, 11189-11201. PMID: 15355100

(40) Brock, A. K., Kozekov, I. D., Rizzo, C. J. and Harris, T. M. (2004) Coupling products of nucleosides with the glyoxal adduct of deoxyguanosine. Chem. Res. Toxicol.17, 1047-1056. PMID: 15310236

(39) West, J. D., Ji, C., Duncan, S. T., Amarnath, V., Schneider, C., Rizzo, C. J., Brash, A. R. and Marnett, L. J. (2004) Induction of apoptosis in colorectal carcinoma cells treated with 4-hydroxy-2-nonenal and structurally related aldehydic products of lipid peroxidation. Chem. Res. Toxicol. 17, 453-462. PMID: 16351098

(38) Wang, H., Marnett, L. J., Harris, T. M. and Rizzo, C. J. (2004) A novel synthesis of malondialdehyde adducts of deoxyguanosine, deoxyadenosine, and deoxycytidine. Chem. Res. Toxicol. 17, 144-149. PMID: 14967001

2003

(37) Rezaei, M., Harris, T. M. and Rizzo, C. J. (2003) Stereoselective synthesis of the 1,N2-deoxyguanosine adducts of cinnamaldehyde.  A stereocontrolled route to deoxyguanosine adducts of α,β-unsaturated aldehydes. Tetrahedron Lett 44, 7513-7516.

(36) Fernandes, P. H., Wang, H., Rizzo, C. J. and Lloyd, R. S. (2003) Site-specific mutagenicity of stereochemically defined 1,N2-deoxyguanosine adducts of trans-4-hydroxynonenal in mammalian cells. Environ. Mol. Mutagen. 42, 68-74. PMID: 12929118

(35) Wang, H., Kozekov, I. D., Harris, T. M. and Rizzo, C. J. (2003) 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. 125, 5687-5700. PMID: 12733907

(34) Kozekov, I. D., Nechev, L. V., Moseley, M. S., Harris, C. M., Rizzo, C. J., Stone, M. P. and Harris, T. M. (2003) DNA interchain cross-links formed by acrolein and crotonaldehyde. J. Am. Chem. Soc. 125, 50-61. PMID: 12515506

2002

(33) Nechev, L. V., Kozekov, I. D., Brock, A. K., Rizzo, C. J. and Harris, T. M. (2002) 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.15, 607-613. PMID: 12018980

(32) Guo, F., Chang, B. H. and Rizzo, C. J. (2002) An N1-hydrogen bonding model for flavin coenzyme. Bioorg. Med. Chem. Lett. 12, 151-154. PMID: 1175534

2001

(31) Wang, H. and Rizzo, C. J. (2001) Stereocontrolled syntheses of all four stereoisomeric 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal. Org. Lett. 3, 3603-3605. PMID: 11678719

(30) Rizzo, C. J. (2001) Further computational studies on the conformation of 1,5-dihydrolumiflavin. Antioxid. Redox Signal. 3, 737-746. PMID: 11761324

(29) Wang, F., Wang, H., Polavarapu, P.L. and Rizzo C. J. (2001) Absolute configuration and conformational stability of (+)-2,5-dimethylthiolane and (-)-2,5-dimethylsulfolane. J Org Chem. 66, 3507-3512. PMID: 11348137

(28) Wang, Z. and Rizzo, C. J. (2001) Synthesis of the C8-deoxyguanosine adduct of the food mutagen IQ. Org. Lett. 3, 565-568. PMID: 11178826

(27) Drabowicz, J., Dudziński, B., Mikołajczyk, M., Wang, F., Dehlavi, A., Goring, J., Park, M., Rizzo, C. J., Polavarapu, P. L., Biscarini, P., Wieczorek, M. W., and Majzner W. R. (2001) Absolute configuration, predominant conformation and vibrational circular dichroism spectra of enantiomers of n-butyl t-butyl sulfoxide. J. Org. Chem. 66, 1122-1129. PMID: 11312938

2000

(26) Wang, Z., Prudhomme, D. R., Buck, J. R., Park, M. and Rizzo, C. J. (2000) Stereocontrolled synthesis of deoxynucleosides via photoinduced electron transfer deoxygenation of benzoyl protected arabino- and ribonucleosides. J. Org. Chem. 65, 5969-5985. PMID: 10987930

(25) Reibenspies, J. H., Guo, F. and Rizzo, C. J. (2000) X-ray crystal structures of conformationally biased flavin models. Org. Lett. 2, 903-906. PMID: 10768182

(24) Wang, Z. and Rizzo, C. J. (2000) Regioselective synthesis of β-N1 and β-N3 alloxazine nucleosides. Org. Lett. 2, 227-230. PMID: 10814288

1999

(23) Prudhomme, D. R., Park,M., Wang, Z., Buck, J. R., and Rizzo, C. J. (1999) Synthesis of deoxyribonucleosides: 3',5'-Di-O-benzoylthymidine. Org. Synth. 77, 162-173.

(22) Buck, J. R., Park, M., Wang, Z., Prudhomme, D. R., and Rizzo, C. J. (1999) 3,6-Dimethyl-9-ethylcarbazole. Org. Synth.77, 153-161.

1998

(21) Park, M., Buck, J. R., and Rizzo, C. J. (1998) A convenient synthesis of 3,6-substituted carbazoles. Tetrahedron,54, 12707-12714.

(20) Hasford, J. J., and Rizzo, C. J. (1998) A linear free energy substituent effect on flavin redox chemistry. J. Am. Chem. Soc. 120, 2251-2255.

(19) Hasford, J. J., and Rizzo, C. J. (1998) Reduction of Hg(II)•EDTA with conformationally biased flavins. Tetrahedron Lett. 39, 1317-1320.

1997

(18) Wang, Z. and Rizzo, C. J. (1997) Stereocontrolled synthesis of α-2'-deoxyribonucleosides.Tetrahedron Lett. 38, 8177-8180.

(17) Prudhomme, D. R., Wang, Z., and Rizzo, C. J. (1997) An improved photosensitizer for the photoinduced electron-transfer deoxygenation of benzoate and m-(trifluoromethyl)benzoates. J. Org. Chem. 62, 8257-8260. PMID: 11671949

(16) Hasford, J. J., Kemnitzer, W., and Rizzo, C. J. (1997) Conformational effects on flavin redox chemistry. J. Org. Chem. 62, 5244-5245.

1996

(15) Park, M., and Rizzo, C. J. (1996) Stereocontrolled, de novo synthesis of β-2'-deoxyribonucleosides. J. Org. Chem. 61, 6092-6093. PMID: 11667437

(14) Brown, S. A., and Rizzo, C. J. (1996) A ‘one-pot’ alkylation/hydrolysis of o-nitrotrifluoroacetanilides.  A convenient route to n-alkyl o-phenylenediamines. Synth. Commun. 26, 4065-4080.

1995

(13) Parker, M. S. A., and Rizzo, C. J.(1995) Facile addition of dichloroketene to acetylenes mediated by zinc and ultrasound. Synth. Commun. 25, 2781-9.

1992

(12) Rizzo, C. J. (1992) Salt effects in a hydrophobically accelerated Diels-Alder reaction follows the Hofmeister series. J. Org. Chem. 1992, 57, 6382-4.

From Graduate and Post-doctoral Work

(11) Smith, A. B., Wood, J. L., Wong, W., Gould, A. E., Rizzo. C. J., Barbosa, J., Funayama, S., Komiyama, K., and Omura, S., (1996) (+)-Trienomycins A, B, C and F and (+)-mycotrienins I and II: Relative and absolute stereochemistry. J. Am. Chem. Soc. 118, 8308-8315.

(10) Smith, A. B., Wood, J. L., Rizzo, C. J., Furst , G. T., Carroll, P. J., Donohue, J., and Omura, S. (1992) (+)-Hitachimycin:  Stereochemistry and conformational analysis. J. Am. Chem. Soc.114 , 8003-8007.

(9) Dougherty, J. P., Rizzo C. J., and Breslow, R. (1992) Oligodeoxynucleotides that contain 2',5'' linkages: Synthesis and hybridization properties. J. Am. Chem. Soc. 114, 6254-6255

(8) Rizzo, C. J., Dougherty J. P., and Breslow, R. (1992) 3'-Deoxy-2'-phosphoramidites of adenosine and 5-methyluridine used for the solid phase synthesis of unnatural 3'-deoxy-2',5''-oligonucleotides. Tetrahedron Lett., 33, 4129-4133.

(7) Breslow, R., and Rizzo, C. J. (1991) Chaotropic salt effects in a hydrophobically accelerated Diels-Alder reaction. J. Am. Chem. Soc. 113, 4340-4341.

(6) Rizzo, C. J., and Smith, A. B. (1991) Aphidicolin synthetic studies:  A stereocontrolled end game. J. Chem. Soc., Perkin Trans. I, 1991, 969-979.

(5) Rizzo, C. J., Wood, J. L., Furst , G. T., an dSmith, A. B. (1990) Aphidicolin synthetic studies, 2. 2D-NMR analysis of (+)-aphidicolin and its degradation products 3a,18-dihydroxy-17-noraphidicolan-16-one and 3a,18-isopropylidenedioxy-17-noraphidicolan-16-one. Complete 1H and 13C assignments. J. Nat. Prod. 1990, 53, 735-739.

(4). Smith, A. B., Wood, J. L., Wong, W., Gould, A. E., Rizzo. C. J., Funayama, S. and Omura, S. (1990) (+)-Trienomycins A, B, and C: Relative and absolute stereochemistry. J. Am. Chem. Soc., 1990, 112, 7425-7426.

(3) Smith, A. B., Wood, J. L., Rizzo. C. J., Furst , G. T., Carroll, P. J., Donohue, J., and Omura, S. (1990) Solution and crystal structures of (+)-hitachimycin (stubomycin). J. Org. Chem. 55, 1133-1135.

(2) Rizzo, C. J., and Smith, A. B. (1990) A new end game for aphidicolin. Tetrahedron Lett.29, 2793-2796

(1) Rizzo, C. J., Dunlap, N. K., and Smith, A. B. (1987) A convenient preparation of 4- and 5-substituted cyclopentenones: A short synthesis of methylenomycin B. J. Org. Chem.52, 5280-5283.

 

Non Peer-Reviewed

(3) Stone, M. P., Huang, H., Cho, Y.-J., Kim,H.-Y., Kozekov, I. D., Kozekova, A., Wang ,H.,. Minko, I. G., Lloyd, R. S., Harris, T. M. and Rizzo, C. J. (2010) Interstrand DNA cross-linking of 1,N2-deoxyguanosine adducts derived from α,β-unsaturated aldehydes: Structure-function relationships, in The Chemical Biology of DNA Damage, Geacintov, N. E., & Broyde, S., Eds., Wiley-VCH, Weinheim, Germany, 2010, pp 203-216

(2) Stover, J. S., Elmquist, C. E., Wang, F., Zang, H., Stone, M. P., Guengerich, F. P., and Rizzo C. J., (2006) Synthesis, conformation, and bypass of carcinogen-modified oligonucleotides. American Association for Cancer Research Education Book, 2006, 207-210.

(1) Rizzo, C. J. (2005) N-Methylcarbazole. Electronic Encyclopedia of Reagents for Organic Synthesis, John Wily & Sons.