Publications
ORCID: 0000-0001-9005-611X SCOPUS ID: 7102642628
2019
(129) Chen, H., Yao, L., Rizzo, C. J., Turesky, R. J. Quantitation of Apurinic/Apyrimidinic Sites in Isolated DNA and in Mammalian Tissue with Reduced Artifact, Anal. Chem., 2019, 91, (accepted). PMID: 31055913
2018
(128) Bamberger, S.N., Malik, C.K., Voehler, M.W., Brown, S.K. Pan, K., Johnson Salyard, T.L., Rizzo, C.J., Stone, M.P., Conformational Equilibria of the N6-(2-Deoxy-D-erythro-pentofuranosyl)-2,6-diamino-3,4-dihydro-4-oxo-5-N-methylformamidopyrimidine (MeFapy-dG) Lesion in DNA. Chem. Res. Toxic. 2018, 924-935. PMCID: PMC6352716
2017
(127) Minko, I.G., Rizzo, C.J., Lloyd, R.S. (2017) Mutagenic Potential of Nitrogen Mustard Formamidopyrimidine DNA Adduct, J. Biol. Chem. 292, 18790-18799. PMCID: PMC5704464
(126) Sha, Y., Minko, I.G., Malik, C.K., Rizzo. C.J., Lloyd, R.S. (2017) Error-prone replication bypass of the imidazole ring-opened formamidopyrimidine deoxyguanosine adduct, Environ. Mol. Mutagen. 58, 182-189. (feature article). PMCID: PMC5476229
2016
(125) Bose, A., Millsap, A..D., DeLeon A., Rizzo, C.J., Basu, A .K. (2016) Translesion Synthesis of the N2-2′-Deoxyguanosine Adduct of the Dietary Mutagen IQ in Human Cells: Error-Free Replication by DNA Polymerase κ and Mutagenic Bypass by DNA Polymerases η, ζ, and Rev1, Chem. Res. Toxicol. 29, 1549-1559. (cover article) PMCID: PMC5031085
(124) Minko, I. G., Jacobs, A. C., Donley, N., Gruppi,F., Harris, T. M., Rizzo,C. J., McCullough, A. K,. Lloyd, R. S. (2016) Catalysts of DNA strand cleavage at apurinic/apyrimidinic sites, Sci. Rep. (Nature), 6, 28894; doi: 10.1038/srep28894. PMCID: PMC4929455
(123) Thiaville, J. J., Kellner, S. M., Yuan, Y., Hutinet, G., Thiaville, P. C., Jumpathong, W., Mohapatra, S., Brochier-Armanet, C., Letarov, A. V., Hillebrand, R., Malik, C. K., Rizzo, C. J. Dedon, P. C., de Crécy-Lagard, V. (2016) Novel genomic island modifies DNA with 7-deazaguanine derivatives, Proc. Natl. Acad. Sci. U.S.A., 113, E1452–E1459. PMCID: PMC4801273
2015
(122) Gruppi, F., Hejzai, L., Christov, P. P., Krishnamachari, S., Turesky, R. J., Rizzo, C. J. (2015) Characterization of nitrogen mustard formamidopyrimidine adduct formation of bis-(2-chloroethyl)ethylamine with calf thymus DNA and human mammary cancer cell line, Chem. Res. Toxicol. 28, 1850-1860. PMCID: PMC4579055
(121) Bose, A., Pande, P., Jasti, V. P., Millsap, A. D., Hawkins, E. K., Rizzo, C. J., Basu, A. K. (2015) DNA polymerases κ and ζ cooperatively perform mutagenic translesion synthesis of the C8-2’-deoxyguanosine adduct of the dietary mutagen IQ in human cells, Nucleic Acids Res. 43, 8340-8351. PMID: 26220181
(120) Stavros, K. M., Hawkins, E. K., Rizzo, C. J., Stone, M. P. (2015) Base-displaced intercalated conformation of the 2-amino-3-methylimidazo[4,5-f]quinolone N2-dG DNA adduct positioned at the non-reiterated G1 in the NarI restriction site, Chem. Res. Toxicol. 28, 1455-1468. PMCID: PMC4511292
(119) Patra, A., Banerjee, S, Johnson-Salyard, T., Malik, C., Christov, P., Rizzo, C. J., Stone, M. P., Egli, M. (2015) Structural basis for error-free bypass of the 5-N-methyl-formamidopyrimidine-dG lesion by human DNA polymerase η and sulfolobus solfataricus P2 polymerase IV (Dpo4), J. Am. Chem. Soc. 137, 7011-7014. PMCID: PMC45452697
(118) Zdżalik, D., Domańska, A., Prorok, P., Kosicki, K., van den Born, E., Falnes, P. Ø., Rizzo, C. J., Guengerich, F. P., Tudek, B. (2015) Differential repair of etheno-DNA adducts by bacterial and human AlkB proteins, DNA Repair, 30, 1-10. PMCID: PMC4451939
(117) Chang, S.-c., Fedeles, B. I., Wu, J., Delaney, J. C., Li, D., Zhao, L., Christov, P. P., Yau, E., Singh, V., Jost, M., Drennan, C. L., Marnett, L. J., Rizzo, C. J., Levine, S. S., Guengerich, F. P., Essigmann, J. M. (2015) Next-generation sequencing reveals the biological significance of the N2,3-ethenoguanine lesion in vivo, Nucleic Acids Res. 43, 5489-5500. PMCID: PMC44776462
2014
(116) Singh, V., Fedeles, B. I., Li, D., Delaney, J. C., Kozekov, I. D., Kozekova, A., Marnett, L. J., Rizzo,C. J., Essigmann, J. M. (2014) Mechanism of repair of the acrolein- and malondialdehyde-derived exocyclic guanine adducts by the α-ketoglutarate/Fe(II) dioxygenase AlkB, Chem. Res. Toxicol. 27, 1619-1631. PMCID: PMC4164229
(115) Christov, P. P., Son, K.-J., Rizzo, C. J. (2014) Synthesis and characterization of oligonucleotides containing a nitrogen mustard formamidopyrimidine monoadduct of deoxyguanosine, Chem. Res. Toxicol. 27, 1610-1618. (cover article) PMCID: PMC4164228
(114) Petrova, K., Millsap, A. D., Stec, D.F., Rizzo, C. J. (2014) Characterization of the deoxyguanosine-lysine cross-link of methylglyoxal, Chem. Res. Toxicol. 27, 1019–1029. PMCID: PMC4060920
(113) Gruppi, F., Johnson-Salyard, T. L., Rizzo, C. J. (2014) Synthesis of G-N2-(CH2)3-N2-G Trimethylene DNA interstrand cross-links, Curr. Prot. Nucleic Acid Chem. 5.14.1–5.14.15 (supplement 56). PMCID: PMC4242527
(112) Stavros, K. M., Hawkins, E. K., Rizzo, C. J., Stone, M. P. (2013) Base-Displaced Intercalation of the 2-Amino-3-methylimidazo[4,5-f]quinolone N2-dG Adduct in the NarI DNA Recognition Sequence, Nucleic Acids Res. 41, 3450-63. PMCID: PMC3950664
2013
(111) Maddukuri, L., Shuck, S., Eoff, R., Zhao, L., Rizzo, C, J., Guengerich, F. P., Marnett, L. J. (2013) Replication, Repair and Translesion Polymerase Bypass of N6-Oxopropenyl-2′-deoxyadenosine, Biochemistry, 52, 8766-8776. PMCID: PMC3925671
(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, 947-953 PMCID: PMC3825762
(109) Shanmugam, G., Minko, I. G., Banerjee, S., Christov, P. P., Kozekov, I. D., Rizzo, C. J., Lloyd, R. S., Egli, M., 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. PMCID: PMC3775444
(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. PMCID: PMC3735235
(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. PMCID: PMC3830661
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. (cover article) 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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. (cover article) 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., 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., 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. (cover article) PMCID: PMC2636699
(76) Stafford, J. B., Eoff, R. L., Kozekova, A., Rizzo, C. J., Guengerich, F. P., 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., 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., 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., 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., 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., 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., 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., 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., Pommier, Y. (2008) The modulation of topoisomerase-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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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. (cover article) 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., 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., 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., 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., 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., 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., 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., Rizzo, C. J. (2004) A novel synthesis of malondialdehyde adducts of deoxyguanosine, deoxyadenosine, and deoxycytidine. Chem. Res. Toxicol. 17, 144-149. (cover article) PMID: 14967001
2003
(37) Rezaei, M., Harris, T. M., 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., 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., 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., 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., 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., 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., 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., 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., 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., 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., Rizzo, C. J. (2000) X-ray crystal structures of conformationally biased flavin models. Org. Lett. 2, 903-906. PMID: 10768182
(24) Wang, Z., 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., 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., Rizzo, C. J. (1999) 3,6-Dimethyl-9-ethylcarbazole. Org. Synth.77, 153-161.
1998
(21) Park, M., Buck, J. R., Rizzo, C. J. (1998) A convenient synthesis of 3,6-substituted carbazoles. Tetrahedron,54, 12707-12714.
(20) Hasford, J. J., 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., Rizzo, C. J. (1998) Reduction of Hg(II)•EDTA with conformationally biased flavins. Tetrahedron Lett. 39, 1317-1320.
1997
(18) Wang, Z., Rizzo, C. J. (1997) Stereocontrolled synthesis of α-2′-deoxyribonucleosides.Tetrahedron Lett. 38, 8177-8180.
(17) Prudhomme, D. R., Wang, Z., 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., Rizzo, C. J. (1997) Conformational effects on flavin redox chemistry. J. Org. Chem. 62, 5244-5245.
1996
(15) Park, M., Rizzo, C. J. (1996) Stereocontrolled, de novo synthesis of β-2′-deoxyribonucleosides. J. Org. Chem. 61, 6092-6093. PMID: 11667437
(14) Brown, S. A., 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., 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., 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., Omura, S. (1992) (+)-Hitachimycin: Stereochemistry and conformational analysis. J. Am. Chem. Soc.114 , 8003-8007.
(9) Dougherty, J. P., Rizzo C. J., 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., 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., 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., Smith, 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. 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., Omura, S. (1990) Solution and crystal structures of (+)-hitachimycin (stubomycin). J. Org. Chem. 55, 1133-1135.
(2) Rizzo, C. J., Smith, A. B. (1990) A new end game for aphidicolin. Tetrahedron Lett.29, 2793-2796
(1) Rizzo, C. J., Dunlap, N. K., 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., 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., 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.