DNA damage and mutagenesis induced by polycyclic aromatic hydrocarbons

The Carcinogenic Effects of Polycyclic Aromatic Hydrocarbons

Volumn , Issue , 2005, Pages 171-210

  Besaratinia, Ahmad ^a   Pfeifer, Gerd P ^a  

^a CITY OF HOPE NATIONAL MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 10644229935     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1142/9781860949333_0005     Document Type: Chapter

References (180)

1. Harvey RG (1991) Environmental occurrence and cancer. In: Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity [Harvey RG (ed.)] pp 11-25, Cambridge University Press, New York.
2. Phillips DH (1999) Polycyclic aromatic hydrocarbons in the diet. Mutat. Res. 443: 139-147.
3. Phillips DH (2002) Smoking-related DNA and protein adducts in human tissues. Carcinogenesis 23: 1979-2004.
4. Kennaway E (1955) The identification of a carcinogenic compound in coal-tar. Br. Med. J. 2: 749-752.
5. Alloway BJ and Ayres DC (1994) Chemical Principles of Environmental Pollution. Blackie Academic & Professional, Glasgow, UK.
6. Phillips DH (1983) Fifty years of benzo[a]pyrene. Nature 303: 468-472.
7. Pullman A and Pullman B (1955) Electronic structure and carcinogenic activity of aromatic molecules. In: Advances in Cancer Research [Greenstein A and Haddow PP (eds.)] pp 117-169, Wiley-Interscience, New York.
8. Harvey RG (1991) Metabolic activation, DNA binding, and mechanisms of carcinogenesis. In: Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity [Harvey RG (ed.)] pp 50-95, Cambridge University Press, New York.
9. Miller JA and Miller EC (1969) The metabolic activation of carcinogenic aromatic amines and amides. Prog. Exp. Tumor Res. 11: 273-301.
10. Miller JA (1970) Carcinogenesis by chemicals: an overview - G.H.A. Clowes Memorial Lecture. Cancer Res. 30: 559-576.
11. Brookes P (1966) Quantitative aspects of the reaction of some carcinogens with nucleic acids and the possible significance of such reactions in the process of carcinogenesis. Cancer Res. 26: 1994-2003.
12. Lawley PD and Brookes P (1964) Methylation of adenine in deoxyadenylic acid or deoxyribonucleic acid at N-7. Biochem. J. 92: 19c-20c.
13. Shih C, Shilo BZ, Goldfarb MP, Dannenberg A and Weinberg RA (1979) Passage of phenotypes of chemically transformed cells via transfection of DNA and chromatin. Proc. Natl. Acad. Sci. USA 76: 5714-5718.
14. Harvey RG (1991) Molecular properties of polyarenes. In: Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity [Harvey RG (ed.)] pp 96-116, Cambridge University Press, New York.
15. Hall M and Grover PL (1990) Polycyclic aromatic hydrocarbons: metabolism, activation and tumour initiation. In: Chemical Carcinogenesis and Mutagenesis [Cooper CS and Grover PL (eds.)] Volume I, pp 327-372, Springer-Verlag, Berlin.
16. Nebert DW and Gonzalez FJ (1987) P450 genes: structure, evolution, and regulation. Annu. Rev. Biochem. 56: 945-993.
17. Armsrong RN (1997) Glutathione-S-transferases. In: Comprehensive Toxicology: Biotransformation [Guengerich FP (ed.)] Volume 3, pp 307-327, Elsevier Science, Oxford, UK.
18. Guenther TM and Oesch F (1981) Microsomal epoxide hydrolase and its role in polycyclic aromatic hydrocarbon transformation. In: Polycyclic Aromatic Hydrocarbons and Cancer [Gelboin HV and Ts’o POP (eds.)] Volume 3, pp 183-212, Academic Press, New York.
19. Burchell B, McGurk K, Brierley CH and Clarke DJ (1997) UDP- glucuronosyltransferases. In: Comprehensive Toxicology: Biotransformation [Guengerich FP (ed.)] Volume 3, pp 401-436, Elsevier Science, Oxford, UK.
20. Duffel MW (1997) Sulfotransferases. In: Comprehensive Toxicology: Biotransformation [Guengerich FP (ed.)] Volume 3, pp 365-384, Elsevier Science, Oxford, UK.
21. Pfeifer GP and Denissenko MF (1998) Formation and repair of DNA lesions in the p53 gene: relation to cancer mutations? Environ. Mol. Mutagen. 31: 197-205.
22. Seo KY, Jelinsky SA and Loechler EL (2000) Factors that influence the mutagenic patterns of DNA adducts from chemical carcinogens. Mutat. Res. 463: 215-246.
23. Jeffrey AM, Weinstein IB, Jennette KW, Grzeskowiak K, Nakanishi K, Harvey RG, Autrup H and Harris C (1977) Structures of benzo[a]pyrene- nucleic acid adducts formed in human and bovine bronchial explants. Nature 269: 348-350.
24. Nakanishi K, Kasai H, Cho H, Harvey RG, Jeffrey AM, Jennette KW and Weinstein I (1977) Absolute configuration of a ribonucleic acid adduct formed in vivo by metabolism of benzo[a]pyrene. J. Am. Chem. Soc. 99: 258-260.
25. Sims P and Grover PL (1981) Involvement of dihydrodiols and diol epoxides in the metabolic activation of polycyclic aromatic hydrocarbons other than benzo[a]pyrene. In: Polycyclic Hydrocarbons and Cancer [Gelboin HV and Ts’o POP (eds.)] pp 117-181, Academic Press, New York.
26. Memory JD and Wilson NK (1982) NMR of Aromatic Compounds. Wiley, New York.
27. Karcher W, Fordham RJ, Dubois JJ, Glaude PG and Lighthart JA (1985) Spectral Atlas of Polycyclic Aromatic Compounds. Reidel, Dordrecht, The Netherlands.
28. Levin W, Chang RL, Wood AW, Thakker DR, Yagi H, Jerina DM and Conney AH (1986) Tumorigenicity of optical isomers of the diastereomeric bay-region 3,4-diol-l,2-epoxides of benzo[c]phenanthrene in murine tumor models. Cancer Res. 46: 2257-2261.
29. Hecht SS, El-Bayoumy K, Rivenson A and Amin S (1994) Potent mammary carcinogenicity in female CD rats of a fjord region diol- epoxide of benzo[c]phenanthrene compared to a bay region diol-epoxide of benzo[a]pyrene. Cancer Res. 54: 21-24.
30. Cavalieri EL, Rogan EG, Higginbotham S, Cremonesi P and Salmasi S (1988) Tumor-initiating activity in mouse skin and carcinogenicity in rat mammary gland of dibenzo[a]pyrenes: the very potent environmental carcinogen dibenzo[a,l]pyrene. J. Cancer Res. Clin. Oncol. 115: 67-72.
31. Cavalieri EL, Higginbotham S, RamaKrishna NV, Devanesan PD, Todo- rovic R, Rogan EG and Salmasi S (1991) Comparative dose-response tumorigenicity studies of dibenzo[a,l]pyrene versus 7,12-dimethylbenz- [a]anthracene, benzo[a]pyrene and two dibenzo[a,l]pyrene dihydrodiols in mouse skin and rat mammary gland. Carcinogenesis 12: 1939-1944.
32. Higginbotham S, RamaKrishna NV, Johansson SL, Rogan EG and Cavalieri EL (1993) Tumor-initiating activity and carcinogenicity of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene and benzo[a]- pyrene at low doses in mouse skin. Carcinogenesis 14: 875-888.
33. Harvey RG (1991) Nomenclature. In: Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity [Harvey RG (ed.)] pp 1-10, Cambridge University Press, New York.
34. Harvey RG (1991) Dihydrodiols. In: Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity [Harvey RG (ed.)] pp 306-329, Cambridge University Press, New York.
35. Weinstein IB, Jeffrey AM, Jennette KW, Blobstein SH, Harvey RG, Harris C, Autrup H, Kasai H and Nakanishi K (1976) Benzo[a]pyrene diol epoxides as intermediates in nucleic acid binding in vitro and in vivo. Science 193: 592-595.
36. Conney AH (1982) Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons: G.H.A. Clowes Memorial Lecture. Cancer Res. 42: 4875-4917.
37. Huberman E, Sachs L, Yang SK and Gelboin V (1976) Identification of mutagenic metabolites of benzo[a]pyrene in mammalian cells. Proc. Natl. Acad. Sci. USA 73: 607-611.
38. Newbold RF and Brookes P (1976) Exceptional mutagenicity of a benzo- [a]pyrene diol epoxide in cultured mammalian cells. Nature 261: 52-54.
39. Melendez-Colon VJ, Smith CA, Seidel A, Luch A, Platt KL and Baird WM (1997) Formation of stable adducts and absence of depurinating DNA adducts in cells and DNA treated with the potent carcinogen dibenzo[a,l]pyrene or its diol epoxides. Proc. Natl. Acad. Sci. USA 94: 13542-13547.
40. Loeb LA (1989) Endogenous carcinogenesis: molecular oncology into the twenty-first century - Presidential address. Cancer Res. 49: 5489-5496.
41. Melendez-Colon VJ, Luch A, Seidel A and Baird WM (1999) Cancer initiation by polycyclic aromatic hydrocarbons results from formation of stable DNA adducts rather than apurinic sites. Carcinogenesis 20: 1885-1891.
42. Rogan EG, Devanesan PD, RamaKrishna NV, Higginbotham S, Padmavathi NS, Chapman K, Cavalieri EL, Jeong H, Jankowiak R and Small GJ (1993) Identification and quantitation of benzo[a]pyrene-DNA adducts formed in mouse skin. Chem. Res. Toxicol. 6: 356-363.
43. Devanesan PD, RamaKrishna NV, Padmavathi NS, Higginbotham S, Rogan EG, Cavalieri EL, Marsch GA, Jankowiak R and Small GJ (1993) Identification and quantitation of 7,12-dimethylbenz[a]anthracene-DNA adducts formed in mouse skin. Chem. Res. Toxicol. 6: 364-371.
44. Li KM, Todorovic R, Cavalieri EL, Rogan EG, Jankowiak R and Small G (1997) Depurinating DNA adducts detected in mouse skin treated with dibenzo[a,l]pyrene (DB [a, l]P), DB [a, l]P-11,12-dihydrodiol, (±)-anti- DB[a,l]P diol epoxide (DE) or (±)-syn-DB[a,l]PDE. Proceedings of the American Association for Cancer Research. American Association for Cancer Research, Volume 38, p 127.
45. Todorovic R, Ariese F, Devanesan P, Jankowiak R, Small GJ, Rogan E and Cavalieri E (1997) Determination of benzo[a]pyrene- and 7,12- dimethylbenz[a]anthracene-DNA adducts formed in rat mammary glands. Chem. Res. Toxicol. 10: 941-947.
46. Todorovic R, Li KM, Rogan EG and Cavalieri EL (1996) Identification and quantitation of DNA adducts of benzo[a]pyrene (BP), 7,12- dimethylbenz[a]anthracene (DMBA) and dibenzo[a,l]pyrene (DB[a,l]P) formed in rat mammary glands. Proceedings of the American Association for Cancer Research. American Association for Cancer Research, Volume 37, p 119.
47. Benzer S and Freese E (1958) Induction of specific mutations with 5-bromo- uracil. Proc. Natl. Acad. Sci. USA 44: 112-119.
48. Benzer S (1961) On the topography of genetic fine structure. Proc. Natl. Acad. Sci. USA 47: 403-415.
49. Maxam AM and Gilbert W (1977) A new method for sequencing DNA. Proc. Natl. Acad. Sci. USA 74: 560-564.
50. Sanger F, Nicklen S and Coulson AR (1977) DNA sequencing with chain- terminating inhibitors. Proc. Natl. Acad. Sci. USA 74: 5463-5467.
51. Saiki RK, Scharf S, Faloona F, Mullis KB, Horn GT, Erlich HA and Amheim N (1985) Enzymatic amplification of beta-globin genomic sequences and restriction site analysis for diagnosis of sickle cell anemia. Science 230: 1350-1354.
52. Mizusawa H, Lee CH, Kakefuda T, McKenney K, Shimatake H and Rosenberg M (1981) Base insertion and deletion mutations induced in an Escherichia coli plasmid by benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide. Proc. Natl. Acad. Sci. USA 78: 6817-6820.
53. Chakrabarti S, MizusawaHand Seidman M (1984) Survival and mutagenesis of bacterial plasmids with localized carcinogen adducts. Mutat. Res. 126: 127-137.
54. Rodriguez H and Loechler EL (1993) Mutational specificity of the (+)-anti-diol epoxide of benzo[a]pyrene in a supF gene of an Escherichia coli plasmid: DNA sequence context influences hotspots, mutagenic specificity and the extent of SOS enhancement of mutagenesis. Carcinogenesis 14: 373-383.
55. Roilides E, Gielen JE, Tuteja N, Levine AS and Dixon K (1988) Mutational specificity of benzo[a]pyrene diol epoxide in monkey cells. Mutat. Res. 198: 199-206.
56. Yang JL, Chen RH, Maher VM and McCormick JJ (1991) Kinds and location of mutations induced by (±)-7β, 8α-dihydroxy-9α, 10α-epoxy- 7.8.9.10- tetrahydrobenzo[a]pyrene in the coding region of the hypoxan- thine (guanine)phosphoribosyltransferase gene in diploid human fibroblasts. Carcinogenesis 12: 71-75.
57. Yang JL, Maher VM and McCormick JJ (1987) Kinds of mutations formed when a shuttle vector containing adducts of (±)-7β,8α-dihydroxy-9α, 10α- epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene replicates in human cells. Proc. Natl. Acad. Sci. USA 84: 3787-3791.
58. Yang JL, Maher VM and McCormick JJ (1987) Kinds of mutations formed when a shuttle vector containing adducts of benzo[a]pyrene-7,8-diol-9,10- epoxide replicates in COS7 cells. Mol. Cell. Biol. 1: 1267-1270.
59. Eisenstadt E, Warren AJ, Porter J, Atkins D and Miller JH (1982) Carcinogenic epoxides of benzo[a]pyrene and cyclopenta[c,d]pyrene induce base substitutions via specific transversions. Proc. Natl. Acad. Sci. USA 79: 1945-1949.
60. Bemelot-Moens C, Glickman BW and Gordon AJ (1990) Induction of specific frameshift and base substitution events by benzo[a]pyrene diol epoxide in excision-repair-deficient Escherichia coli. Carcinogenesis 11: 781-785.
61. Wei SJ, Chang RL, Wong CQ, Bhachech N, Cui XX, Hennig E, Yagi H, Sayer JM, Jerina DM, Preston BD and Conney AH (1991) Dose-dependent differences in the profile of mutations induced by an ultimate carcinogen from benzo[a]pyrene. Proc. Natl. Acad. Sci. USA 88: 11227-11230.
62. Wei SJ, Chang RL, Bhachech N, Cui XX, Merkler KA, Wong CQ, Hennig E, Yagi H, Jerina DM and Conney AH (1993) Dose-dependent differences in the profile of mutations induced by (+)-7R,8S-dihydroxy-9S,10R-epoxy- 7.8.9.10-tetrahydrobenzo[a]pyrene in the coding region of the hypoxanthine (guanine) phosphoribosyltransferase gene in Chinese hamster V-79 cells. Cancer Res. 53: 3294-3301.
63. Chen RH, Maher VM, Brouwer J, van de Putte P and McCormick JJ (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.
64. Chen RH, Maher VM and McCormick JJ (1991) Lack of a cell cycle- dependent strand bias for mutations induced in the HPRT gene by (±)-7β, 8α- dihydroxy-9α, 10α-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene in excision repair-deficient human cells. Cancer Res. 51: 2587-2592.
65. Chen RH, Maher VM and McCormick JJ (1990) Effect of excision repair by diploid human fibroblasts on the kinds and locations of mutations induced by (±)-7y3,8α-dihydroxy-9α, 10α-epoxy-7,8,9,10-tetrahydro- benzo[a]pyrene in the coding region of the HPRT gene. Proc. Natl. Acad. Sci. USA 87: 8680-8684.
66. Wei SJ, Chang RL, Hennig E, Cui XX, Merkler KA, Wong CQ, Yagi H, Jerina DM and Conney AH (1994) Mutagenic selectivity at the HPRT locus in V-79 cells: comparison of mutations caused by bay-region benzo[a]pyrene 7,8- diol-9,10-epoxide enantiomers with high and low carcinogenic activity. Carcinogenesis 15: 1729-1735.
67. Keohavong P and Thilly WG (1992) Mutational spectrometry: a general approach for hot-spot point mutations in selectable genes. Proc. Natl. Acad. Sci. USA 89: 4623-4627.
68. Andersson B, Fait S and Lambert B (1992) Strand specificity for mutations induced by (+)-anti-BPDE in the hprt gene in human T-lymphocytes. Mutat. Res. 269: 129-140.
69. Jakubczak JL, Merlino G, French JE, Muller WJ, Paul B, Adhya S and Garges S (1996) Analysis of genetic instability during mammary tumor progression using a novel selection-based assay for in vivo mutations in a bacteriophage lambda transgene target. Proc. Natl. Acad. Sci. USA 93:9073-9078.
70. Skopek TR, Kort KL, Marino DR, Mittal LV, Umbenhauer DR, Laws GM and Adams SP (1996) Mutagenic response of the endogenous hprt gene and lacl transgene in benzo[a]pyrene-treated Big Blue B6C3F1 mice. Environ. Mol. Mutagen. 28: 376-384.
71. Bigger CA, Ponten I, Page JE and Dipple A (2000) Mutational spectra for polycyclic aromatic hydrocarbons in the supF target gene. Mutat. Res. 450: 75-93.
72. Chen J and Thilly WG (1996) Mutational spectra vary with exposure conditions: benzo[a]pyrene in human cells. Mutat. Res. 357: 209-217.
73. BasuAK and Essigmann JM (1988) Site-specifically modified oligodeoxynu- cleotides as probes for the structural and biological effects of DNA-damaging agents. Chem. Res. Toxicol. 1: 1-18.
74. Loechler EL (1996) The role of adduct site-specific mutagenesis in understanding how carcinogen-DNA adducts cause mutations: perspective, prospects and problems. Carcinogenesis 17: 895-902.
75. Singer B and Essigmann JM (1991) Site-specific mutagenesis: retrospective and prospective. Carcinogenesis 12: 949-955.
76. 2-Gua, the major adduct of activated benzo[a]pyrene, when studied in an Escherichia coli plasmid using site-directed methods. Carcinogenesis 13: 1415-1425.
77. 2-Gua adduct of the (+)-anti-benzo[a]pyrene diol epoxide is capable of inducing G → A and G → C, in addition to G → T, mutations. Biochemistry 34: 13545-13553.
78. 2-deoxyguanosine adducts of 7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene: configuration of the adduct bond is more important than those of the hydroxyl groups. Biochemistry 36: 13263-13269.
79. 2- dG adduct of (+)-anti-B[a]PDE shows a dramatically different mutagenic specificity (predominantly, G → A) in a 5′-CGT-3′ sequence context. Biochemistry 36: 10256-10261.
80. Guimaraes DP and Hainaut P (2002) TP53: a key gene in human cancer. Biochimie 84: 83-93.
81. Robles AI, Linke SP and Harris CC (2002) The p53 network in lung carcinogenesis. Oncogene 21: 6898-6907.
82. Sills RC, Boorman GA, Neal JE, Hong HL and Devereux TR (1999) Mutations in ras genes in experimental tumours of rodents. IARC Sci. Publ. 55-86.
83. Maronpot RR, Fox T, Malarkey DE and Goldsworthy TL (1995) Mutations in the ras proto-oncogene: clues to etiology and molecular pathogenesis of mouse liver tumors. Toxicology 101: 125-156.
84. Bos JL (1989) Ras oncogenes in human cancer: a review. Cancer Res. 49: 4682-4689.
85. Lowy DR and Willumsen BM (1993) Function and regulation of ras. Annu. Rev. Biochem. 62: 851-891.
86. Moriya M, Spiegel S, Fernandes A, Amin S, Liu T, Geacintov N and GrollmanAP (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.
87. Page JE, Zajc B, Oh-hara T, Lakshman MK, Sayer JM, Jerina DM and Dipple A (1998) Sequence context profoundly influences the mutagenic potency of tram-opened benzo[a]pyrene 7,8-diol 9,10-epoxide-purine nucleoside adducts in site-specific mutation studies. Biochemistry 37:9127-9137.
88. Tsao H, Mao B, Zhuang P, Xu R, Amin S and Geacintov NE (1998) Sequence dependence and characteristics of bends induced by site-specific polynuclear aromatic carcinogen-deoxyguanosine lesions in oligonucleotides. Biochemistry 37: 4993-5000.
89. Kozack RE and Loechler EL (1997) Molecular modeling of the conformational complexity of (+)-anti-B [a]PDE-adducted DNA using simulated annealing. Carcinogenesis 18: 1585-1593.
90. 2-dG adduct of (+)-anti-B[a]PDE induces G→A mutations in a 5′-AGA-3′ sequence context. Carcinogenesis 20: 261-268.
91. Perlow RA and Broyde S (2001) Evading the proofreading machinery of a replicative DNA polymerase: induction of a mutation by an environmental carcinogen. J. Mol. Biol. 309: 519-536.
92. Lin CH, Huang X, Kolbanovskii A, Hingerty BE, Amin S, Broyde S, Geacintov NE and Patel DJ (2001) Molecular topology of polycyclic aromatic carcinogens determines DNA adduct conformation: a link to tumori- genic activity. J. Mol. Biol. 306: 1059-1080.
93. 2-dG) in the eight conformations and the five DNA sequences most relevant to base substitution mutagenesis. Carcinogenesis 20: 85-94.
94. 2-dG) causes G → T versus G → A mutations based upon a correlation between mutagenesis and molecular modeling results. Carcinogenesis 20: 95-102.
95. Seo KY, Jelinsky SA and Loechler EL (2000) Factors that influence the mutagenic patterns of DNA adducts from chemical carcinogens. Mutat. Res. 463: 215-246.
96. 2-dG) of the potent environmental carcinogen, benzo[a]pyrene. Mutat. Res. 450: 41-59.
97. Lavrukhin OV and Lloyd RS (1998) Mutagenic replication in a human cell extract of DNAs containing site-specific and stereospecific benzo[a]pyrene- 7,8- diol-9,10-epoxide DNA adducts placed on the leading and lagging strands. Cancer Res. 58: 887-891.
98. Buterin T, Hess MT, Luneva N, Geacintov NE, Amin S, Kroth H, Seidel A and Naegeli H (2000) Unrepaired fjord region polycyclic aromatic hydrocarbon- DNA adducts in ras codon 61 mutational hot spots. Cancer Res. 60: 1849-1856.
99. 1H NMR. Biochemistry 35: 6212-6224.
100. Cosman M, Laryea A, Fiala R, Hingerty BE, Amin S, Geacintov NE, Broyde S and Patel DJ (1995) Solution conformation of the (-)-trans-anti- benzo[c]phenanthrene-dA ([BPh]dA) adduct opposite dT in a DNA duplex: intercalation of the covalently attached benzo[c]phenanthrenyl ring to the 3′-side of the adduct site and comparison with the (+)-trans-anti-[BPh]dA opposite dT stereoisomer. Biochemistry 34: 1295-1307.
101. Cosman M, Fiala R, Hingerty BE, Laryea A, Lee H, Harvey RG, Amin S, Geacintov NE, Broyde S and Patel DJ (1993) Solution conformation of the (+)-trans-anti-[BPh]dA adduct opposite dT in a DNA duplex: intercalation of the covalently attached benzo[c]phenanthrene to the 5′-side of the adduct site without disruption of the modified base pair. Biochemistry 32: 12488-12497.
102. 6-amino group to (-)-(7S,8R,9R, 10S)-7,8-dihydroxy- 9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene. Biochemistry 34:1364-1375.
103. Laryea A, Cosman M, Lin JM, Liu T, Agarwal R, Smirnov S, Amin S, Harvey RG, Dipple A and Geacintov NE (1995) Direct synthesis and characterization of site-specific adenosyl adducts derived from the binding of a 3,4-dihydroxy-1,2-epoxybenzo[c]phenanthrene stereoisomer to an 11-mer oligodeoxyribonucleotide. Chem. Res. Toxicol. 8: 444-454.
104. Doublie S and Ellenberger T (1998) The mechanism of action of T7 DNA polymerase. Curr. Opin. Struct. Biol. 8: 704-712.
105. Beard WA and Wilson SH (1998) Structural insights into DNA polymerase beta fidelity: hold tight if you want it right. Chem. Biol. 5: R7-R13.
106. Steitz TA (1999) DNA polymerases: structural diversity and common mechanisms. J. Biol. Chem. 214: 17395-17398.
107. Goodman MF, Creighton S, Bloom LB and Petruska J (1993) Biochemical basis of DNA replication fidelity. Crit. Rev. Biochem. Mol. Biol. 28: 83-126.
108. Friedberg EC, Walker GC and Siede W (1995) DNA Repair and Mutagenesis. ASM Press, Washington, D.C.
109. Woodgate R (1999) A plethora of lesion-replicating DNA polymerases. Genes Dev. 13: 2191-2195.
110. Friedberg EC, Wagner R and Radman M (2002) Specialized DNA polymerases, cellular survival, and the genesis of mutations. Science 296: 1627-1630.
111. Goodman MF (2002) Error-prone repair DNA polymerases in prokaryotes and eukaryotes. Annu. Rev. Biochem. 71: 17-50.
112. Hübscher U, Maga G and Spadari S (2002) Eukaryotic DNA polymerases. Annu. Rev. Biochem. 71: 133-163.
113. Lipinski LJ, Ross HL, Zajc B, Sayer JM, Jerina DM and Dipple A (1998) Effect of single benzo[a]pyrene diol epoxide-deoxyguanosine adducts on the action of DNA polymerases in vitro. Int. J. Oncol. 13: 269-273.
114. Keohavong P, Shukla R, Melacrinos A, Day BW and Reha-Krantz L (1998) Effects of bulky polycyclic aromatic hydrocarbon adducts on DNA replication by exonuclease-deficient T7 and T4 DNA polymerases. DNA Cell Biol. 17: 541-549.
115. Thrall BD, Mann DB, Smerdon MJ and Springer DL (1992) DNA polymerase, RNA polymerase and exonuclease activities on a DNA sequence modified by benzo[a]pyrene diol epoxide. Carcinogenesis 13: 1529-1534.
116. Hruszkewycz AM, Canella KA, Peltonen K, Kotrappa L and Dipple A (1992) DNA polymerase action on benzo[a]pyrene-DNA adducts. Carcinogenesis 13: 2347-2352.
117. Friedberg EC and Gerlach VL (1999) Novel DNA polymerases offer clues to the molecular basis of mutagenesis. Cell 98: 413-416.
118. Burgers PM, Koonin EV, Bruford E, Blanco L, Burtis KC, Christman MF, Copeland WC, Friedberg EC, Hanaoka F, Hinkle DC, Lawrence CW, Nakanishi M, Ohmori H, Prakash L, Prakash S, Reynaud CA, Sugino A, Todo T, Wang Z, Weill JC and Woodgate R (2001) Eukaryotic DNA polymerases: proposal for a revised nomenclature. J. Biol. Chem. 276: 43487-43490.
119. Johnson RE, Prakash S and Prakash L (2000) The human DINB1 gene encodes the DNA polymerase Pol J. Proc. Natl. Acad. Sci. USA 97: 3838-3843.
120. Ross JA and Nesnow S (1999) Polycyclic aromatic hydrocarbons: correlations between DNA adducts and ras oncogene mutations. Mutat. Res. 424: 155-166.
121. Nesnow S, Ross JA, Stoner GD and Mass MJ (1995) Mechanistic linkage between DNA adducts, mutations in oncogenes and tumorigenesis of carcinogenic environmental polycyclic aromatic hydrocarbons in strain A/J mice. Toxicology 105: 403-413.
122. Ross JA, Nelson GB, Wilson KH, Rabinowitz JR, Galati A, Stoner GD, Nesnow S and Mass MJ (1995) Adenomas induced by polycyclic aromatic hydrocarbons in strain A/J mouse lung correlate with time-integrated DNA adduct levels. Cancer Res. 55: 1039-1044.
123. McDonald JP, Rapic-Otrin V, Epstein JA, Broughton BC, Wang X, Lehmann AR, Wolgemuth DJ and Woodgate R (1999) Novel human and mouse homologs of Saccharomyces cerevisiae DNA polymerase eta. Genomics 60: 20-30.
124. Gibbs PE, McGregor WG, Maher VM, Nisson P and Lawrence CW (1998) A human homolog of the Saccharomyces cerevisiae REV3 gene, which encodes the catalytic subunit of DNA polymerase zeta. Proc. Natl. Acad. Sci. USA 95: 6876-6880.
125. Ogi T, Kato T Jr, Kato T and Ohmori H (1999) Mutation enhancement by DINB1, a mammalian homologue of the Escherichia coli mutagenesis protein dinB. Genes Cells 4: 607-618.
126. Gerlach VL, Aravind L, Gotway G, Schultz RA, Koonin EV and Friedberg EC (1999) Human and mouse homologs of Escherichia coli DinB (DNA polymerase IV), members of the UmuC/DinB superfamily. Proc. Natl. Acad. Sci. USA 96: 11922-11927.
127. Masutani C, Araki M, Yamada A, Kusumoto R, Nogimori T, Maekawa T, Iwai S and Hanaoka F (1999) Xeroderma pigmentosum variant (XP-V) correcting protein from HeLa cells has a thymine dimer bypass DNA polymerase activity. EMBO J. 18: 3491-3501.
128. Masutani C, Kusumoto R, Yamada A, Dohmae N, Yokoi M, Yuasa M, Araki M, Iwai S, Takio K and Hanaoka F (1999) The XPV (xeroderma pigmentosum variant) gene encodes human DNA polymerase eta. Nature 399: 700-704.
129. Matsuda T, Bebenek K, Masutani C, Hanaoka F and Kunkel TA (2000) Low fidelity DNA synthesis by human DNA polymerase-eta. Nature 404: 1011-1013.
130. Johnson RE, Washington MT, Prakash S and Prakash L (2000) Fidelity of human DNA polymerase eta. J. Biol. Chem. 275: 7447-7450.
131. Johnson RE, Kondratick CM, Prakash S and Prakash L (1999) HRAD30 mutations in the variant form of xeroderma pigmentosum. Science 285: 263-265.
132. Haracska L, Yu SL, Johnson RE, Prakash L and Prakash S (2000) Efficient and accurate replication in the presence of 7,8-dihydro-8-oxoguanine by DNA polymerase eta. Nat. Genet. 25: 458-461.
133. Masutani C, Kusumoto R, Iwai S and Hanaoka F (2000) Mechanisms of accurate translesion synthesis by human DNA polymerase eta. EMBO J. 19: 3100-3109.
134. Chiapperino D, Kroth H, Kramarczuk IH, Sayer JM, Masutani C, Hanaoka F, Jerina DM and Cheh AM (2002) Preferential misincorporation of purine nucleotides by human DNA polymerase eta opposite benzo[a]pyrene 7,8- diol 9,10-epoxide deoxyguanosine adducts. J. Biol. Chem. 277: 11765-11771.
135. Ohashi E, Ogi T, Kusumoto R, Iwai S, Masutani C, HanaokaF and Ohmori II (2000) Error-prone bypass of certain DNA lesions by the human DNA polymerase kappa. Genes Dev. 14: 1589-1594.
136. Ohashi E, Bebenek K, Matsuda T, Feaver WJ, Gerlach VL, Friedberg EC, Ohmori H and Kunkel TA (2000) Fidelity and processivity of DNA synthesis by DNA polymerase kappa, the product of the human DINB1 gene. J. Biol. Chem. 275: 39678-39684.
137. Zhang Y, Yuan F, Xin H, Wu X, Rajpal DK, Yang D and Wang Z (2000) Human DNA polymerase kappa synthesizes DNA with extraordinarily low fidelity. Nucleic Acids Res. 28: 4147-4156.
138. O-Wang J, Kawamura K, Tada Y, Ohmori H, Kimura H, Sakiyama S and Tagawa M (2001) DNA polymerase kappa, implicated in spontaneous and DNA damage-induced mutagenesis, is overexpressed in lung cancer. Cancer Res. 61: 5366-5369.
139. Ogi T, Mimura J, Hikida M, Fujimoto H, Fujii-KuriyamaY and Ohmori H (2001) Expression of human and mouse genes encoding pol κ: testis-specific developmental regulation and AhR-dependent inducible transcription. Genes Cells 6: 943-953.
140. 2-BPDE (7,8-dihydroxy-anti-9, 10-epoxy-7,8,9,10- tetrahydrobenzo[a]pyrene). Biochemistry 41: 6100-6106.
141. Ogi T, Shinkai Y, Tanaka K and Ohmori H (2002) Pol kappa protects mammalian cells against the lethal and mutagenic effects of benzo[a]pyrene. Proc. Natl. Acad. Sci. USA 99: 15548-15553.
142. 6-dA lesions catalyzed by DNA bypass polymerases. J. Biol. Chem. 211: 30488-30494.
143. Zhang Y, Wu X, Rechkoblit O, Geacintov NE, Taylor JS and Wang Z (2002) Response of human REV1 to different DNA damage: preferential dCMP insertion opposite the lesion. Nucleic Acids Res. 30: 1630-1638.
144. Zhang Y, Wu X, Guo D, Rechkoblit O and Wang Z (2002) Activities of human DNA polymerase kappa in response to the major benzo[a]pyrene DNA adduct: error-free lesion bypass and extension synthesis from opposite the lesion. DNA Repair 1: 559-569.
145. 2-dG adducts by human DNA polymerases eta and kappa. Mutat. Res. 510: 23-35.
146. Doublie S, Tabor S, Long AM, Richardson CC and Ellenberger T (1998) Crystal structure of a bacteriophage T7 DNA replication complex at 2.2 Å resolution. Nature 391: 251-258.
147. Kool ET (1998) Replication of non-hydrogen bonded bases by DNA polymerases: a mechanism for steric matching. Biopolymers 48: 3-17.
148. Morales JC and Kool ET (1998) Efficient replication between non-hydrogen- bonded nucleoside shape analogs. Nat. Struct. Biol. 5: 950-954.
149. Kool ET, Morales JC and Guckian KM (2000) Mimicking the structure and function of DNA: insights into DNA stability and replication. Angew. Chem. Int. Ed. Engl. 39: 990-1009.
150. Alekseyev YO, Dzantiev L and Romano LJ (2001) Effects of benzo[a]pyrene DNA adducts on Escherichia coli DNA polymerase I (Klenow fragment) primer-template interactions: evidence for inhibition of the catalytically active ternary complex formation. Biochemistry 40: 2282-2290.
151. Tang D, Phillips DH, Stampfer M, Mooney LA, Hsu Y, Cho S, Tsai WY, Ma J, Cole KJ, She MN and Perera FP (2001) Association between carcinogen- DNA adducts in white blood cells and lung cancer risk in the physicians health study. Cancer Res. 61: 6708-6712.
152. IARC (1994) Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Volume 60: Some Industrial Chemicals. International Agency for Research on Cancer, Lyon, France.
153. Altman D (1991) Practical Statistics for Medical Research. Chapman and Hall, London, UK.
154. Besaratinia A, Kleinjans JC and van Schooten FJ (2002) Biomonitoring of tobacco smoke carcinogenicity by dosimetry of DNA adducts and genotyping and phenotyping of biotransformational enzymes: a review on polycyclic aromatic hydrocarbons. Biomarkers 7: 209-229.
155. Hainaut P and Pfeifer GP (2001) Patterns of p53 G → T transversions in lung cancers reflect the primary mutagenic signature of DNA-damage by tobacco smoke. Carcinogenesis 22: 367-374.
156. Pfeifer GP, Denissenko MF, Olivier M, Tretyakova N, Hecht SS and Hainaut P (2002) Tobacco smoke carcinogens, DNA damage and p53 mutations in smoking-associated cancers. Oncogene 21: 7435-7451.
157. Wistuba II, Gazdar AF and Minna JD (2001) Molecular genetics of small cell lung carcinoma. Semin. Oncol. 28: 3-13.
158. Rodenhuis S and Slebos RJ (1992) Clinical significance of ras oncogene activation in human lung cancer. Cancer Res. 52, Suppl: 2665s-2669s.
159. Slebos RJ, Hruban RH, Dalesio O, Mooi WJ, Offerhaus GJ and Rodenhuis S (1991) Relationship between K-ras oncogene activation and smoking in adenocarcinoma of the human lung. J. Natl. Cancer Inst. 83: 1024-1027.
160. Denissenko MF, Chen JX, Tang MS and Pfeifer GP (1997) Cytosine methyl- ation determines hot spots of DNA damage in the human p53 gene. Proc. Natl. Acad. Sci. USA 94: 3893-3898.
161. Denissenko MF, Pao A, Pfeifer GP and Tang M (1998) Slow repair of bulky DNA adducts along the nontranscribed strand of the human p53 gene may explain the strand bias of transversion mutations in cancers. Oncogene 16: 1241-1247.
162. Denissenko MF, Pao A, Tang M and Pfeifer GP (1996) Preferential formation of benzo[a]pyrene adducts at lung cancer mutational hotspots inp53. Science 274: 430-432.
163. Smith LE, Denissenko MF, Bennett WP, Li H, Amin S, Tang M and Pfeifer GP (2000) Targeting of lung cancer mutational hotspots by polycyclic aromatic hydrocarbons. J. Natl. Cancer Inst. 92: 803-811.
164. Chen JX, Zheng Y, West M and Tang MS (1998) Carcinogens preferentially bind at methylated CpG in the p53 mutational hot spots. Cancer Res. 58: 2070-2075.
165. Feng Z, Hu W, Chen JX, Pao A, Li H, Rom W, Hung MC and Tang MS (2002) Preferential DNA damage and poor repair determine ras gene mutational hotspot in human cancer. J. Natl. Cancer Inst. 94: 1527-1536.
166. Pfeifer GP, Chen HH, Komura J and Riggs AD (1999) Chromatin structure analysis by ligation-mediated and terminal transferase-mediated polymerase chain reaction. Methods Enzymol. 304: 548-571.
167. Pfeifer GP, Tanguay RL, Steigerwald SD and Riggs AD (1990) In vivo footprint and methylation analysis by PCR-aided genomic sequencing: comparison of active and inactive X chromosomal DNA at the CpG island and promoter of human PGK-1. Genes Dev. 4: 1277-1287.
168. Pfeifer GP, Steigerwald SD, Hansen RS, Gartler SM and Riggs AD (1990) Polymerase chain reaction-aided genomic sequencing of an X chromosome-linked CpG island: methylation patterns suggest clonal inheritance, CpG site autonomy, and an explanation of activity state stability. Proc. Natl. Acad. Sci. USA 87: 8252-8256.
169. Geacintov NE, Shahbaz M, Ibanez V, Moussaoui K and Harvey RG (1988) Base-sequence dependence of noncovalent complex formation and reactivity of benzo[a]pyrene diol epoxide with polynucleotides. Biochemistry 27: 8380-8387.
170. Johnson WS, He QY and Tomasz M (1995) Selective recognition of the mSCpG dinucleotide sequence in DNA by mitomycin C for alkylation and cross-linking. Bioorg. Med. Chem. 3: 851-860.
171. Yoon JH, Smith LE, Feng Z, Tang M, Lee CS and Pfeifer GP (2001) Methylated CpG dinucleotides are the preferential targets for G-to-T transversion mutations induced by benzo[a]pyrene diol epoxide in mammalian cells: similarities with the p53 mutation spectrum in smoking-associated lung cancers. Cancer Res. 61:7110-7117.
172. Mumford JL, He XZ, Chapman RS, Cao SR, Harris DB, Li XM, Xian YL, Jiang WZ, Xu CW, Chuang JC, Wilson WE and Cooke M (1987) Lung cancer and indoor air pollution in Xuan Wei, China. Science 235: 217-220.
173. Lan Q, He X, Costa DJ, Tian L, Rothman N, Hu G and Mumford JL (2000) Indoor coal combustion emissions, GSTM1 and GSTT1 genotypes, and lung cancer risk: a case-control study in Xuan Wei, China. Cancer Epidemiol. Biomarkers Prev. 9: 605-608.
174. Mumford JL, Li X, Hu F, Lu XB and Chuang JC (1995) Human exposure and dosimetry of polycyclic aromatic hydrocarbons in urine from Xuan Wei, China with high lung cancer mortality associated with exposure to unvented coal smoke. Carcinogenesis 16: 3031-3036.
175. Casale GP, Singhal M, Bhattacharya S, RamaNathan R, Roberts KP, Barbacci DC, Zhao J, Jankowiak R, Gross ML, Cavalieri EL, Small GJ, Rennard SI, Mumford JL and Shen M (2001) Detection and quantification of depurinated benzo[a]pyrene-adducted DNA bases in the urine of cigarette smokers and women exposed to household coal smoke. Chem. Res. Toxicol. 14: 192-201.
176. DeMarini DM, Landi S, Tian D, Hanley NM, Li X, Hu F, Roop BC, Mass MJ, Keohavong P, Gao W, Olivier M, Hainaut P and Mumford JL (2001) Lung tumor KRAS and TPS3 mutations in nonsmokers reflect exposure to PAH-rich coal combustion emissions. Cancer Res. 61: 6679-6681.
177. Rideout WM 3rd, Coetzee GA, Olumi AF and Jones PA (1990) 5-Methyl- cytosine as an endogenous mutagen in the human LDL receptor and p53 genes. Science 249: 1288-1290.
178. Shen JC, Rideout WM 3rd and Jones PA (1992) High frequency mutagenesis by a DNA methyltransferase. Cell 71: 1073-1080.
179. Tretyakova N, Matter B, Jones R and Shallop A (2002) Formation of benzo[a]pyrene diol epoxide-DNA adducts at specific guanines within K-ras and p53 gene sequences: stable isotope-labeling mass spectrometry approach. Biochemistry 41: 9535-9544.
180. Hussain SP, Amstad P, Raja K, Sawyer M, Hofseth L, Shields PG, Hewer A, Phillips DH, Ryberg D, Haugen A and Harris CC (2001) Mutability of p53 hotspot codons to benzo[a]pyrene diol epoxide (BPDE) and the frequency of p53 mutations in nontumorous human lung. Cancer Res. 61: 6350-6355.