Base Pair Conformation-Dependent Excision of Benzo[a]Pyrene Diol Epoxide-Guanine Adducts by Human Nucleotide Excision Repair Enzymes

References

• Aboussekhra, A., M. Biggerstaff, M. K. K. Shivji, J. A. Vilpo, V. Moncollin, V. N. Podust, M. Protic, U. Hubscher, J.-M. Egly, and R. D. Wood. 1995. Mammalian DNA nucleotide excision repair reconstituted with purified components. Cell 80:859–868.
   PubMed Web of Science ®Google Scholar
• Bohr, V. A., C. A. Smith, D. S. Okumoto, and P. C. Hanawalt. 1985. DNA repair in an active gene: removal of pyrimidine dimers from the DHFR gene of CHO cells is much more efficient than in the genome overall. Cell 40:359–369.
   PubMed Web of Science ®Google Scholar
• Chen, R.-H., V. M. Maher, J. Brouwer, P. van de Putte, and J. J. McCormick. 1992. Preferential repair and strand-specific repair of benzo[a]pyrene diol epoxide adducts in the HPRT gene of diploid human fibroblasts. Proc. Natl. Acad. Sci. USA 89:5413–5417.
   PubMed Web of Science ®Google Scholar
• Cheng, S. C., B. D. Hilton, J. M. Roman, and A. Dipple. 1989. DNA adducts from carcinogenic and noncarcinogenic enantiomers of benzo[a]pyrene dihydrodiol epoxide. Chem. Res. Toxicol. 2:334–340.
   PubMed Web of Science ®Google Scholar
• Conney, A. H. 1982. Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons. Cancer Res. 42:4875–4917.
   PubMed Web of Science ®Google Scholar
• Cosman, M., V. Ibanez, N. E. Geacintov, and R. G. Harvey. 1990. Preparation and isolation of adducts in high yield derived from the binding of two benzo[a]pyrene-7,8-dihydroxy-9,10-oxide stereoisomers to the oligonucleotide d(ATATGTATA). Carcinogenesis 11:1667–1672.
   PubMed Web of Science ®Google Scholar
• Cosman, M., C. de los Santos, R. Fiala, B. E. Hingerty, S. B. Singh, V. Ibanez, L. A. Margulis, D. Live, N. E. Geacintov, S. Broyde, and D. J. Patel. 1992. Solution conformation of the major adduct between the carcinogen (+)-anti-benzo[a]pyrene diol epoxide and DNA. Proc. Natl. Acad. Sci. USA 89:1914–1918.
   PubMed Web of Science ®Google Scholar
• Cosman, M., C. de los Santos, R. Fiala, B. E. Hingerty, V. Ibanez, E. Luna, R. G. Harvey, N. E. Geacintov, S. Broyde, and D. J. Patel. 1993. Solution conformation of the (+)-cis-anti-[BP]dG adduct in a DNA duplex: intercalation of the covalently attached benzo[a]pyrenyl ring into the helix and displacement of the modified deoxyguanosine. Biochemistry 32:4145–4155.
   PubMed Web of Science ®Google Scholar
• Cosman, M., R. Fiala, B. E. Hingerty, S. Amin, N. E. Geacintov, S. Broyde, and D. J. Patel. 1994. Solution conformation of the (+)-trans-anti-[BP]dG adduct opposite a deletion site in a DNA duplex: intercalation of the covalently attached benzo[a]pyrene in the helix with base displacement of the modified deoxyguanosine into the major groove. Biochemistry 33:11507–11517.
   PubMed Web of Science ®Google Scholar
• Cosman, M., R. Fiala, B. E. Hingerty, S. Amin, N. E. Geacintov, S. Broyde, and D. J. Patel. 1994. Solution conformation of the (+)-cis-anti-[BP]dG adduct opposite a deletion site in a DNA duplex: intercalation of the covalently attached benzo[a]pyrene in the helix with base displacement of the modified deoxyguanosine into the minor groove. Biochemistry 33:11518–11527.
   PubMed Web of Science ®Google Scholar
• Cosman, M., B. E. Hingerty, N. Luneva, S. Amin, N. E. Geacintov, S. Broyde, and D. J. Patel. 1996. Solution conformation of the (-)-cis-anti-benzo- [a]pyrenyl-dG adduct opposite dC in a DNA duplex: intercalation of the covalently attached BP ring into the helix with base displacement of the modified deoxyguanosine into the major groove. Biochemistry 35:9850–9863.
   PubMedGoogle Scholar
• de los Santos, C., M. Cosman, B. E. Hingerty, V. Ibanez, L. A. Margulis, N. E. Geacintov, S. Broyde, and D. J. Patel. 1992. Influence of benzo- [a]pyrene diol epoxide chirality on solution conformations of DNA covalent adducts: the (-)-trans-anti-[BP]G z C adduct structure and comparison with the (+)-trans-anti-[BP]G z C enantiomer. Biochemistry 31:5245–5252.
   PubMed Web of Science ®Google Scholar
• Fountain, M. A., and T. R. Krugh. 1995. Structural characterization of a (+)-trans-anti-benzo[a]pyrene-DNA adduct using NMR, restrained energy minimization, and molecular dynamics. Biochemistry 34:3152–3161.
   PubMed Web of Science ®Google Scholar
• Friedberg, E. C., G. C. Walker, and W. Siede. 1995. DNA repair and mutagenesis. American Society for Microbiology, Washington, D.C.
   Google Scholar
• Fuchs, R. P. P., and M. Daune. 1971. Physical studies on deoxyribonucleic acid after covalent binding of a carcinogen. Biochemistry 11:2659–2666.
   Google Scholar
• Gao, S., R. Drouin, and G. P. Holmquist. 1994. DNA repair rates mapped along the human PGK1 gene at nucleotide resolution. Science 263:1438–1440.
   PubMed Web of Science ®Google Scholar
• Geacintov, N. E., M. Cosman, B. Mao, A. Alfano, V. Ibanez, and R. G. Harvey. 1991. Spectroscopic characteristics and site I/II classification of cis and trans benzo[a]pyrene diol epoxide enantiomer-guanosine adducts in oligonucleotides and polynucleotides. Carcinogenesis 12:2099–2108.
   PubMed Web of Science ®Google Scholar
• Grunberger, D., J. H. Nelson, C. R. Cantor, and I. B. Weinstein. 1970. Coding and conformational properties of oligonucleotides modified with the carcinogen N-2-acetylaminofluorene. Proc. Natl. Acad. Sci. USA 66:488–494.
   PubMed Web of Science ®Google Scholar
• Gunz, D., M. T. Hess, and H. Naegeli. 1996. Recognition of DNA adducts by human nucleotide excision repair. J. Biol. Chem. 271:25089–25098.
   PubMed Web of Science ®Google Scholar
• Hanawalt, P. C. 1994. Transcription-coupled repair and human diseases. Science 266:1957–1958.
   PubMed Web of Science ®Google Scholar
• Hansson, J., M. Munn, W. D. Rupp, R. Kahn, and R. D. Wood. 1989. Localization of DNA repair synthesis by human cell extracts to a short region at the site of a lesion. J. Biol. Chem. 264:21788–21792.
   PubMedGoogle Scholar
• Hess, M. T., N. E. Geacintov, and H. Naegeli. Unpublished data.
   Google Scholar
• Hess, M. T., U. Schwitter, M. Petretta, B. Giese, and H. Naegeli. 1996. Site-specific DNA substrates for human excision repair: comparison between deoxyribose and base adducts. Chem. Biol. 3:121–128.
   PubMedGoogle Scholar
• Hess, M. T., U. Schwitter, M. Petretta, B. Giese, and H. Naegeli. 1997. Bipartite substrate discrimination by human nucleotide excision repair. Proc. Natl. Acad. Sci. USA 94:6664–6669.
   PubMedGoogle Scholar
• Huang, J.-C., D. Svoboda, J. T. Reardon, and A. Sancar. 1992. Human nucleotide excision nuclease removes thymine dimers from DNA by incising the 22nd phosphodiester bond 5′ and the 6th phosphodiester bond 3′ to the photodimer. Proc. Natl. Acad. Sci. USA 89:3664–3668.
   PubMed Web of Science ®Google Scholar
• Huang, J.-C., D. S. Hsu, A. Kazantsev, and A. Sancar. 1994. Substrate spectrum of human excinuclease: repair of abasic sites, methylated bases, mismatches, and bulky adducts. Proc. Natl. Acad. Sci. USA 91:12213–12217.
   PubMed Web of Science ®Google Scholar
• Manley, J. L., A. Fire, A. Cano, P. A. Sharp, and M. L. Gefter. 1980. DNA-dependent transcription of adenovirus genes in a soluble whole-cell extract. Proc. Natl. Acad. Sci. USA 77:3855–3859.
   PubMed Web of Science ®Google Scholar
• Matsunaga, T., D. Mu, C.-H. Park, J. T. Reardon, and A. Sancar. 1995. Human DNA repair excision nuclease. J. Biol. Chem. 270:20862–20869.
   PubMedGoogle Scholar
• Mellon, I., G. Spivak, and P. C. Hanawalt. 1987. Selective removal of transcription-blocking DNA damage from the transcribed strand of the mammalian DHFR gene. Cell 51:241–249.
   PubMed Web of Science ®Google Scholar
• Mitchell, D. L., and R. S. Nairn. 1989. The biology of the (6-4) photoproduct. Photochem. Photobiol. 49:805–819.
   PubMed Web of Science ®Google Scholar
• Moggs, J. G., K. J. Yarema, J. M. Essigmann, and R. D. Wood. 1996. Analysis of incision sites produced by human cell extracts and purified proteins during nucleotide excision repair of a 1,3-intrastrand d(GpTpG)- cisplatin adduct. J. Biol. Chem. 271:7177–7186.
   PubMedGoogle Scholar
• Moggs, J. G., D. E. Szymkowski, M. Yamada, P. Karran, and R. D. Wood. 1997. Differential human nucleotide excision repair of paired and mispaired cisplatin-DNA adducts. Nucleic Acids Res. 25:480–490.
   PubMedGoogle Scholar
• Moriya, M., S. Spiegel, A. Fernandes, S. Amin, T. Liu, N. E. Geacintov, and A. P. Grollman. 1996. Fidelity of translesional synthesis past benzo[a]pyrene diol epoxide-2′-deoxyguanosine DNA adducts: marked effects of host cell, sequence context, and chirality. Biochemistry 35:16646–16651.
   PubMed Web of Science ®Google Scholar
• Mu, D., E. Bertrand-Burggraf, J. J. Huang, R. P. P. Fuchs, and A. Sancar. 1994. Human and E. coli excinucleases are affected differently by the sequence context of acetylaminofluorene-guanine adduct. Nucleic Acids Res. 22:4869–4871.
   PubMedGoogle Scholar
• Mu, D., D. S. Hsu, and A. Sancar. 1996. Reaction mechanism of human DNA repair excision nuclease. J. Biol. Chem. 271:8285–8294.
   PubMed Web of Science ®Google Scholar
• Mu, D., M. Tursun, D. R. Duckett, J. T. Drummond, P. Modrich, and A. Sancar. 1997. Recognition and repair of compound DNA lesions (base damage and mismatch) by human mismatch repair and excision repair systems. Mol. Cell. Biol. 17:760–769.
   PubMed Web of Science ®Google Scholar
• Naegeli, H. 1997. Mechanisms of DNA damage recognition in mammalian cells. R. G. Landes, Austin, Tex.
   Google Scholar
• O’Handley, S. F., D. G. Sanford, R. Xu, C. C. Lester, B. E. Hingerty, S. Broyde, and T. R. Krugh. 1993. Structural characterization of an N-acetyl- 2-aminofluorene (AAF) modified DNA oligomer by NMR, energy minimization, and molecular dynamics. Biochemistry 32:2481–2497.
   PubMed Web of Science ®Google Scholar
• Ponten, I., S. K. Kim, A. Gräslund, B. Nordén, and B. Jernström. 1994. Synthesis and characterization of a (+)-anti-benzo[a]pyrene 7,8-dihydrodiol 9,10-epoxide-oligonucleotide adduct, p. 433–436. In K. Hemminki, D. E. G. Dipple, F. F. Shuker, D. Kadlubar, D. Segerback, and H. Bartsch (ed.), DNA adducts: identification and biological significance. International Agency for Research on Cancer scientific publication no. 125. International Agency for Research on Cancer, Lyon, France.
   Google Scholar
• Reardon, J. T., L. H. Thompson, and A. Sancar. 1997. Rodent UV-sensitive mutant cell lines in complementation groups 6-10 have normal general excision repair activity. Nucleic Acids Res. 25:1015–1021.
   PubMedGoogle Scholar
• Ruggieri, B., M. DiRado, S. Y. Zhang, B. Bauer, T. Goodrow, and A. J. P. Klein-Szanto. 1993. Benzo[a]pyrene-induced murine skin tumors exhibit frequent and characteristic G to T mutations in the p53 gene. Proc. Natl. Acad. Sci. USA 90:1013–1017.
   PubMedGoogle Scholar
• Sancar, A. 1996. DNA excision repair. Annu. Rev. Biochem. 65:43–81.
   PubMed Web of Science ®Google Scholar
• Shibutani, S., L. A. Margulis, N. E. Geacintov, and A. P. Grollman. 1993. Translesional synthesis on a DNA template containing single stereoisomers of dG-(+)- or dG-(-)-anti-BPDE (7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10- tetrahydrobenzo[a]pyrene). Biochemistry 32:7531–7541.
   PubMed Web of Science ®Google Scholar
• Tornaletti, S., and G. P. Pfeifer. 1994. Slow repair of pyrimidine dimers at p53 mutation hotspots in skin cancer. Science 263:1436–1438.
   PubMed Web of Science ®Google Scholar
• Veaute, X., and R. P. P. Fuchs. 1991. Polymorphism in N-2-acetylaminofluorene induced DNA structure as revealed by DNase I footprinting. Nucleic Acids Res. 19:5603–5606.
   PubMedGoogle Scholar
• Venema, J., Z. Bartosova, A. T. Natarajan, A. A. van Zeeland, and L. H. F. Mullenders. 1992. Transcription affects the rate but not the extent of repair of cyclobutane pyrimidine dimers in the human adenosine deaminase gene. J. Biol. Chem. 267:8852–8856.
   PubMedGoogle Scholar
• Vousden, K. H., J. L. Bos, C. J. Marshall, and D. H. Phillips. 1986. Mutations activating human c-Ha-ras1 protooncogene (HRAS1) induced by chemical carcinogens and depurination. Proc. Natl. Acad. Sci. USA 83:1222–1226.
   PubMed Web of Science ®Google Scholar
• Wei, D., V. M. Maher, and J. J. McCormick. 1995. Site-specific rates of excision repair of benzo[a]pyrene diol epoxide adducts in the hypoxanthine phophoribosyltransferase gene of human fibroblasts: correlation with mutation spectra. Proc. Natl. Acad. Sci. USA 92:2204–2208.
   PubMedGoogle Scholar
• Wei, D., V. M. Maher, and J. J. McCormick. 1996. Site-specific excision repair of 1-nitrosopyrene-induced DNA adducts at the nucleotide level in the HPRT gene of human fibroblasts: effect of adduct conformation on the pattern of site-specific repair. Mol. Cell. Biol. 16:3714–3719.
   PubMedGoogle Scholar
• Wei, S.-J. C., R. L. Chang, E. Hennig, X. X. Cui, K. A. Merkler, C.-Q. Wong, H. Yagi, and A. H. Conney. 1994. Mutagenic selectivity at the HPRT locus in V-79 cells: comparison of mutations caused by bay-region benzo[a]pyrene 7,8-9,10-epoxide enantiomers with high and low carcinogenic activity. Carcinogenesis 15:1729–1735.
   PubMed Web of Science ®Google Scholar
• Wood, R. D., P. Robins, and T. Lindahl. 1988. Complementation of the xeroderma pigmentosum DNA repair defect in cell-free extracts. Cell 53:97–106.
   PubMed Web of Science ®Google Scholar
• Wood, R. D. 1996. DNA repair in eukaryotes. Annu. Rev. Biochem. 65:135–167.
   PubMed Web of Science ®Google Scholar
• Xu, R., S. Amin, and N. E. Geacintov. Unpublished data.
   Google Scholar
• Xu, R., S. Birke, S. E. Carberry, N. E. Geacintov, C. E. Swenberg, and R. G. Harvey. 1992. Differences in unwinding of supercoiled DNA induced by the two enantiomers of anti-benzo[a]pyrene diol epoxide. Nucleic Acids Res. 20:6167–6176.
   PubMedGoogle Scholar
• Xu, R., B. Mao, J. Xu, B. Li, S. Birke, C. E. Swenberg, and N. E. Geacintov. 1995. Stereochemistry-dependent bending in oligonucleotide duplexes induced by site-specific covalent benzo[a]pyrene diol epoxide-guanine lesions. Nucleic Acids Res. 23:2314–2319.
   PubMed Web of Science ®Google Scholar
• Ya, N.-Q., S. Smirnov, M. Cosman, S. Bhanot, V. Ibanez, and N. E. Geacintov. 1994. Thermal stabilities of benzo[a]pyrene diol epoxide-modified oligonucleotide duplexes. Effects of mismatched complementary strands and bulges, p. 349–366. In R. H. Sarma and M. H. Sarma (ed.), Structural biology: the state of the art. Proceedings of the 8th conversation. Adenine Press, Schenectady, N.Y.
   Google Scholar
• Zegar, I. S., S. J. Kim, T. N. Johansen, P. J. Horton, C. M. Harris, T. M. Harris, and M. P. Stone. 1996. Adduction of the human N-ras codon 61 sequence with (-)-(7S,8R,9R,10S)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetra- hydrobenzo[a]pyrene: structural refinement of the intercalated SRSR(61,2) (-)-(7S,8R,9R,10S)-N6-[10-(7,8,9,10-tetrahydrobenzo[a]pyrenyl)]-2′-de- oxyadenosyl adduct from 1H NMR. Biochemistry 35:6212–6224.
   PubMed Web of Science ®Google Scholar
• Zou, Y., T. Liu, N. E. Geacintov, and B. Van Houten. 1995. Interaction of the UvrABC nuclease with a DNA duplex containing a single stereoisomer of dG-(+)- or dG-(-)-anti-BPDE. Biochemistry 34:13582–13593.
   PubMedGoogle Scholar