Factors that influence the mutagenic patterns of DNA adducts from chemical carcinogens

Mutation Research - Reviews in Mutation Research

Volumn 463, Issue 3, 2000, Pages 215-246

  Seo, Kwang Young ^a   Jelinsky, Scott A ^a   Loechler, Edward L ^a  

^a Boston University   (United States)

Author keywords

Adduct conformation; Cancer; Genotoxins; Mutational spectrum; Mutations; Site specific mutagenesis

Indexed keywords

CARCINOGEN; CELL DNA; DNA POLYMERASE;

CANCER RISK; CELL SPECIFICITY; CHEMICAL CARCINOGENESIS; CHEMICAL MUTAGENESIS; DNA ADDUCT; GENE MUTATION; GENOTOXICITY; HUMAN; MOLECULAR DYNAMICS; NONHUMAN; PRIORITY JOURNAL; REVIEW; RISK FACTOR; SITE DIRECTED MUTAGENESIS;

EID: 0033804390     PISSN: 13835742     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1383-5742(00)00047-8     Document Type: Article

References (208)

1. Hollstein M., Hergenhahn M., Yang Q., Bartsch H., Wang Z.Q., Hainaut P. New approaches to understanding p53 gene tumor mutation spectra. Mutat. Res. 431:1999;199-209.
2. Vogelstein B., Kinzler K.W. Carcinogens leave fingerprints. Nature. 355:1992;209-210.
3. Greenblatt M.S., Bennett W.P., Hollstein M., Harris C.C. Perspectives in cancer research: mutations in the p53 tumor suppressor gene: clues to cancer etiology and molecular pathogenesis. Cancer Res. 54:1994;4855-4878.
4. Hainaut P., Hernandez T., Robinson A., Rodriguez-Tome P., Flores T., Hollstein M., Harris C.C. IARC database of p53 gene mutations in human tumors and cell lines: updated compilation, revised formats and new visualisation tools. Nucleic Acids Res. 26:1998;205-213.
5. Nagase H., Nakamura Y. Mutations of the APC (Adenomatous Polyposis Coli) gene. Hum. Mutat. 2:1993;425.
6. Miyaki M.et al. Characteristics of somatic mutation of the adenomatous polyposis coli gene in colorectal tumors. Cancer Res. 54:1994;3011-3020.
7. Brash D.E.et al. A role for sunlight in skin cancer: UV-induced p53 mutations in squamous cell carcinoma. Proc. Natl. Acad. Sci. U.S.A. 88:1991;10124.
8. Dumaz N., Stary A., Soussi T., Daya-Grosjean L., Sarasin A. Can we predict solar ultraviolet radiation as the causal event in human tumors by analyzing the mutation spectra of the p53 gene? Mutat. Res. 307:1994;375.
9. Daya-Grosjean L., Dumaz N., Sarasin A. The specificity of p53 mutation spectra in sunlight induced human cancers. J. Photochem. Photobiol., B. 28:1995;115-124.
10. D'errico M., Calcagnile A., Dogliotti E. Genetic alterations in skin cancer. Ann. Ist. Super. Sanita. 32:1996;53-63.
11. Hsieh D.P., Atkinson D.N. Recent aflatoxin exposure and mutation at codon 249 of the human p53 gene: lack of association. Food Addit. Contam. 12:1995;421-424.
12. Takeshima Y., Seyama T., Bennett W.P., Akiyama M., Tokuoka S., Inai K., Mabuchi K., Land C.E., Harris C.C. p53 mutations in lung cancers from non-smoking atomic-bomb survivors. Lancet. 342:1993;1520.
13. Denissenko M.F., Pao A., Tang M., Pfeifer G.P. Preferential formation of benzo[a]pyrene adducts at lung cancer mutational hotspots in p53. Science. 274:1996;430-432.
14. Denissenko M.F., Pao A., Pfeifer G.P., Tang M.-S. Slow repair of bulky DNA adducts along three nontranscribed strand of the human p53 gene may explain the strand bias of transversion mutations in cancers. Oncogene. 16:1998;1241-1247.
15. El-Bayoumy K. Environmental carcinogens that may be involved in human breast cancer etiology. Chem. Res. Toxicol. 5:1992;585-590.
16. Hoffmann D., Hoffmann I. The changing cigarette, 1950-1995. J. Toxicol. Environ. Health. 50:1997;307-364.
17. G.M. Cooper, Oncogenes 2nd edn. Jones and Bartlett Publishers International, London, England, 1995.
18. J.H. Miller, The lacI gene, in: J.H. Miller, W.S. Reznikoff (Eds.), The Operon, 2nd edn., Cold Spring Harbor Press, Cold Spring Harbor, NY, 1980, pp. 31-88.
19. Miller J.H. Mutagenic specificity in bacteria. Annu. Rev. Genet. 17:1983;215-238.
20. 6-methylguanine built into a unique site in a viral genome. Proc. Natl. Acad. Sci. U.S.A. 81:1984;6271-6275.
21. 4-methylthymine in vivo determined by an enzymatic approach to site-specific mutagenesis. Proc. Natl. Acad. Sci. U.S.A. 83:1986;8501-8505.
22. Singer B., Essigmann J.M. Site-specific mutagenesis: retrospective and prospective. Carcinogenesis. 12:1991;949-955.
23. Basu A.K., Essigmann J.M. Site-specifically modified oligodeoxynucleotides as probes for the structural and biological effects of DNA-damaging agents. Chem. Res. Toxicol. 1:1988;1-18.
24. Eckert K.A., Ingle C.A., Klinedinst D.K., Drinkwater N.R. Molecular analysis of mutations induced in human cells by N-ethyl-N-nitrosourea. Mol. Carcinog. 1:1988;50-56.
25. 2-ethyldeoxythymidine in transversion mutagenesis by ethylating agents. Nucleic Acids Res. 20:1992;587-594.
26. 2-ethylthymidine. Biochemistry. 31:1992;4181-4188.
27. 6-substituted guanine-induced mutagenesis of ras oncogenes. Proc. Natl. Acad. Sci. U.S.A. 86:1989;8650-8654.
28. 4-methylthymine in Escherichia coli using double-stranded and gapped plasmids. Carcinogenesis. 19:1998;457-461.
29. 6-substituted guanine residues in double-stranded or gapped plasmids. Biochemistry. 34:1995;8924-8930.
30. Moriya M., Spiegel S., Fernandes A., Amin S., Liu T.-M., Geacintov N.E., Grollman A.P. Fidelity of translesion synthesis past benzo[a]pyrene diol epoxide-2′-deoxyguanosine DNA adducts: marked effects of host cell, sequence context, and chirality. Biochemistry. 35:1996;16646-16651.
31. Page J.E., Zajc B., Oh-hara T., Lakshman M.K., Sayer J.M., Jerina D.M., Dipple A. Sequence context profoundly influences the mutagenic potency of trans-opened benzo[a]pyrene 7,8-diol 9,10-epoxide-purine nucleoside adducts in site-specific mutation studies. Biochemistry. 37:1998;9127-9137.
32. 6 at the second position of N-ras codon 61. J. Biol. Chem. 270:1995;4990-5000.
33. 6 is dependent on both chirality of the lesion and the local sequence context. J. Biol. Chem. 268:1993;23427-23434.
34. 2-2′-deoxyguanosine adducts in Escherichia coli and simian kidney cells. Biochemistry. 37:1998;10164-10172.
35. 2-Gua, when studied in an Escherichia coli plasmid using site-directed methods. Carcinogenesis. 13:1992;1415-1425.
36. 2-dG adduct of (+)-anti-B[a]PDE induces G→A mutations in a 5′-AGA-3′ sequence context. Carcinogenesis. 20:1999;261-268.
37. Shibutani S., Fernandes A., Suzuki N., Zhou L., Johnson F., Grollman A.P. Mutagenesis of the N-(deoxyguanosin-8-yl)-2-amino-1-methyl-6-phenylimidazo[4, 5-b]pyridine DNA adduct in mammalian cells. Sequence context effects. J. Biol. Chem. 274:1999;27433-27438.
38. J.C. Delaney, J.M. Essigmann, Context-dependent mutagenesis by DNA lesions, Chem. Biol., 6, 743-753.
39. Hoffmannn G.R., Fuchs R.P. Mechanisms of frameshift mutations: insights from aromatic amines. Chem. Res. Toxicol. 10:1997;347-359.
40. Burnouf D., Koehl P., Fuchs R.P.P. Single adduct mutagenesis: strong effect of the position of a single acetylaminofluorene adduct within a mutation hot spot. Proc. Natl. Acad. Sci. U.S.A. 86:1989;4147-4151.
41. Lambert I.B., Napolitano R.L., Fuchs R.P.P. Carcinogen-induced frameshift mutagenesis in repetitive sequences. Proc. Natl. Acad. Sci. U.S.A. 89:1992;1310-1314.
42. Broschard T.H., Koffel-Schwartz N., Fuchs R.P. Sequence-dependent modulation of frameshift mutagenesis at NarI-derived mutation hot spots. J. Mol. Biol. 288:1999;191-199.
43. E.L. Loechler, Mechanism by which aflatoxins and other bulky carcinogens induce mutations, The Toxicology of Aflatoxins: Human Health, Veterinary, and Agricultural Significance vol. 8 Academic Press, Orlando, 1994, pp. 149-178, Chap. 8.
44. Shibutani S., Takeshita M., Grollman A.P. Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature. 349:1991;431-434.
45. Kuchino Y., Mori F., Kasai H., Inoue H., Iwai S., Miura K., Ohtsuka E., Nishimura S. Misreading of DNA templates containing 8-hydroxydeoxyguanosine at the modified base and at adjacent residues. Nature. 327:1987;77-79.
46. Moriya M., Zhang W., Johnson F., Grollman A.P. Mutagenic potency of exocyclic DNA adducts: marked differences between Escherichia coli and simian kidney cells. Proc. Natl. Acad. Sci. U.S.A. 91:1994;11899-11903.
47. 4-ethenocytosine, and 4-amino-5-(imidazol-2-yl)imidazole. Biochemistry. 32:1993;12793-12801.
48. Palejwala V.A., Rzepka R.W., Humayun M.Z. UV irradiation of Escherichia coli modulates mutagenesis at a site-specific ethenocytosine residue on M13 DNA. Evidence for an inducible recA-independent effect. Biochemistry. 32:1993;4112-4120.
49. Palejwala V.A., Simha D., Humayun M.Z. Mechanisms of mutagenesis by exocyclic DNA adducts. Transfection of M13 viral DNA bearing a site-specific adduct shows that ethenocytosine is a highly efficient RecA-independent mutagenic noninstructional lesion. Biochemistry. 30:1991;8736-8743.
50. Bichara M., Fuchs R.P. DNA binding and mutation spectra of the carcinogen N-2-aminofluorene in Escherichia coli. A correlation between the conformation of the premutagenic lesion and the mutation specificity. J. Mol. Biol. 183:1985;341-351.
51. Koffel-Schwartz N., Verdier J.M., Bichara M., Freund A.M., Daune M.P., Fuchs R.P. Carcinogen-induced mutation spectrum in wild-type, uvrA and umuC strains of Escherichia coli. Strain specificity and mutation-prone sequences. J. Mol. Biol. 177:1984;33-51.
52. Fuchs R.P., Schwartz N., Daune M.P. Hot spots of frameshift mutations induced by the ultimate carcinogen N-acetoxy-N-2-acetylaminofluorene. Nature. 294:1981;657-659.
53. Patel D.J., Mao B., Gu Z., Hingerty B.E., Gorin A., Basu A.K., Broyde S. Nuclear magnetic resonance solution structures of covalent aromatic amine-DNA adducts and their mutagenic relevance. Chem. Res. Toxicol. 11:1998;391-407.
54. Reid T.M., Lee M.S., King C.M. Mutagenesis by site-specific arylamine adducts in plasmid DNA: enhancing replication of the adducted strand alters mutation frequency. Biochemistry. 29:1990;6153-6161.
55. R.S. Tebbs, L.J. Romano, Mutagenesis at a site-specifically modified NarI sequence by acetylated and deacetylated aminofluorene adducts. Biochemistry, 33, 8998-9006.
56. Napolitano R.L., Lambert I.B., Fuchs R.P. DNA sequence determinants of carcinogen-induced frameshift mutagenesis. Biochemistry. 33:1994;1311-1315.
57. 2-dG adducts of B[a]PDE: configuration of the adduct bond is more important than of the hydroxyl groups. Biochemistry. 36:1997;13263-13269.
58. Vandewiele D., Borden A., O'Grady P.I., Woodgate R., Lawrence C.W. Efficient translesion replication in the absence of Escherichia coli Umu proteins and 3′-5′ exonuclease proofreading function. Proc. Natl. Acad. Sci. U.S.A. 95:1998;15519-15524.
59. Christner D.F., Lakshmanm M.K., Sayer J.M., Jerina D.M., Dipple A. Primer extension by various polymerases using oligonucleotide templates containing stereoisomeric benzo[a]pyrene-deoxyadenosine adducts. Biochemistry. 33:1994;14297-14305.
60. Chary P., Lloyd R.S. In vitro replication by prokaryotic and eukaryotic polymerases on DNA templates containing site-specific and stereospecific benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide adducts. Nucleic Acids Res. 23:1995;1398-1405.
61. Latham G.J., Harris C.M., Harris T.M., Lloyd R.S. The efficiency of translesion synthesis past single styrene oxide DNA adducts in vitro is polymerase-specific. Chem. Res. Toxicol. 8:1995;422-430.
62. 4-etheno-2′-deoxycytidine in reactions catalyzed by mammalian DNA polymerases. Biochemistry. 35:1996;14992-14998.
63. Shibutani S., Grollman A.P. On the mechanism of frameshift (deletion) mutagenesis in vitro. J. Biol. Chem. 268:1993;11703-11710.
64. S. Shibutani, L.A. Margulis, N.E. Geacintov, A.P. Grollman, Translesional synthesis on a DNA template containing a single stereoisomer of dG-(+)- or dG-(-)-anti-BPDE (7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene). Biochemistry, 32, 7531-7541.
65. Belguise-Valladier P., Fuchs R.P. N-2-aminofluorene and N-2 acetylaminofluorene adducts: the local sequence context of an adduct and its chemical structure determine its replication properties. J. Mol. Biol. 249:1995;903-913.
66. Belguise-Valladier P., Maki H., Sekiguchi M., Fuchs R.P. Effect of single DNA lesions on in vitro replication with DNA polymerase III holoenzyme. Comparison with other polymerases. J. Mol. Biol. 236:1994;151-164.
67. Lindsley J.E., Fuchs R.P. Use of single-turnover kinetics to study bulky adduct bypass by T7 DNA polymerase. Biochemistry. 33:1994;764-772.
68. Rodriguez H., Loechler E.L. Mutational spectra of the (+)-anti-diol epoxide of senzo[a]pyrene in a supF gene of an Escherichia coli plasmid: DNA sequence context influences hotspots, mutational specificity and the extent of SOS enhancement of mutagenesis. Carcinogenesis. 14:1993;373-383.
69. Rodriguez H., Loechler E.L. Mutagenesis by the (+)-anti-diol epoxide of benzo[a]pyrene: what controls mutagenic specificity? Biochemistry. 32:1993;1759-1769.
70. E.C. Friedberg, G.W. Walker, W. Siede, DNA Repair and Mutagenesis, American Society for Microbiology, Washington, DC, 1995, pp. 407-464.
71. Palejwala V.A., Wang G.E., Murphy H.S., Humayun M.Z. Functional recA, lexA, umuD, umuC, polA, and polB genes are not required for the Escherichia coli UVM response. J. Bacteriol. 177:1995;6041-6048.
72. Janel-Bintz R., Maenhaut-Michel G., Fuchs R.P. MucAB but not UmuDC proteins enhance -2 frameshift mutagenesis induced by N-2-acetylaminofluorene at alternating GC sequences. Mol. Gen. Genet. 245:1994;279-285.
73. Rangarajan S., Gudmundsson G., Qiu Z., Foster P.L., Goodman M.F. Escherichia coli DNA polyerase II catalyzes chromosomal and episomal DNA synthesis in vivo. Proc. Natl. Acad. Sci. U.S.A. 94:1997;946-951.
74. Rangarajan S., Woodgate R., Goodman M.F. A phenotype for enigmatic DNA polymerase II: a pivotal role for pol II in replication restart in UV-irradiated Escherichia coli. Proc. Natl. Acad. Sci. U.S.A. 96:1999;9224-9229.
75. Escarceller M., Hicks J., Gudmundsson G., Trump G., Touati D., Lovett S., Foster P.L., McEntee K., Goodman M.F. Involvement of Escherchia coli DNA polymerase II in response to oxidative damage and adaptive mutation. J. Bacteriol. 176:1994;6221-6228.
76. Foster P.L., Gudmundsson G., Trimarchi J.M., Cai H., Goodman M.F. Proofreading-defective DNA polymerase II increases adaptive mutation in Escherichia coli. Proc. Natl. Acad. Sci. U.S.A. 92:1995;7951-7955.
77. Kim S.R., Maenhaut-Michel G., Yamada M., Yamamoto Y., Matsui K., Sofuni T., Nohmi T., Ohmori H. Multiple pathways for SOS-induced mutagenesis in Escherichia coli: an overexpression of dinB/dinP results in strongly enhancing mutagenesis in the absence of any exogenous treatment to damage DNA. Proc. Natl. Acad. Sci. U.S.A. 94:1997;13792-13797.
78. Berardini M., Foster P., Loechler E.L. DNA polymerase II (polB) is involved in a new DNA repair pathway for DNA interstrand cross-links in Escherichia coli. J. Bacteriol. 181:1999;2878-2882.
79. Tomer G., Livneh Z. Analysis of unassisted translesion replication by the DNA polymerase III holoenzyme. Biochemistry. 38:1999;5948-5958.
80. Fuchs R.P., Napolitano R.L. Inactivation of DNA proofreading obviates the need for SOS induction in frameshift mutagenesis. Proc. Natl. Acad. Sci. U.S.A. 95:1998;13114-13119.
81. Burnouf D.Y., Miturski R., Fuchs R.P. Sequence context modulation of translesion synthesis at a single N-2-acetylaminofluorene adduct located within a mutation hot spot. Chem. Res. Toxicol. 12:1999;144-150.
82. Wagner J., Gruz P., Kim S.R., Yamada M., Matsui K., Fuchs R.P., Nohmi T. The dinB gene encodes a novel E. coli DNA polymerase, DNA pol IV, involved in mutagenesis. Mol. Cell. 4:1999;281-286.
83. Tang M., Shen X., Frank E.G., O'Donnell M., Woodgate R., Goodman M.F. UmuD′(2)C is an error-prone DNA polymerase, Escherichia coli pol V. Proc. Natl. Acad. Sci. U.S.A. 96:1999;8919-8924.
84. Tang M., Bruck I., Eritja R., Turner J., Frank E.G., Woodgate R., O'Donnell M., Goodman M.F. Biochemical basis of SOS-induced mutagenesis in Escherichia coli: reconstitution of in vitro lesion bypass dependent on the UmuD′2C mutagenic complex and RecA protein. Proc. Natl. Acad. Sci. U.S.A. 95:1998;9755-9760.
85. Smith B.T., Walker G.C. Mutagenesis and more: umuDC and the Escherichia coli SOS response. Genetics. 148:1998;1599-1610.
86. Reuven N.B., Tomer G., Livneh Z. The mutagenesis proteins UmuD′ and UmuC prevent lethal frameshifts while increasing base substitution mutations. Mol. Cell. 2:1998;191-199.
87. Burgers P.M. Eukaryotic DNA polymerases in DNA replication and DNA repair. Chromosoma. 107:1998;218-227.
88. Wood R.D., Shivji M.K. Which DNA polymerases are used for DNA-repair in eukaryotes? Carcinogenesis. 18:1997;605-610.
89. S. Waga, B. Stillman, The DNA replication fork in eukaryotic cells, Annu. Rev. Biochem., 67, 721-751.
90. Gibbs P.E., McGregor W.G., Maher V.M., Nisson P., Lawrence C.W. A human homolog of the Saccharomyces cerevisiae REV3 gene, which encodes the catalytic subunit of DNA polymerase zeta. Proc. Natl. Acad. Sci. U.S.A. 95:1998;6876-6880.
91. Nelson J.R., Lawrence C.W., Hinkle D.C. Deoxycytidyl transferase activity of yeast REV1 protein. Nature. 382:1996;729-731.
92. Nelson J.R., Lawrence C.W., Hinkle D.C. Thymine-thymine dimer bypass by yeast DNA polymerase zeta. Science. 272:1996;1646-1649.
93. Baynton K., Bresson-Roy A., Fuchs R.P. Analysis of damage tolerance pathways in Saccharomyces cerevisiae: a requirement for Rev3 DNA polymerase in translesion synthesis. Mol. Cell Biol. 18:1998;960-966.
94. Lawrence C.W., Hinkle D.C. DNA polymerase zeta and the control of DNA damage induced mutagenesis in eukaryotes. Cancer Surv. 28:1996;21-31.
95. Friedberg E.C., Gerlach V.L. Novel DNA polymerases offer clues to the molecular basis of mutagenesis. Cell. 98:1999;413-416.
96. Masutani C., Kusumoto R., Yamada A., Dohmae N., Yokoi M., Araki M., Yuasa M., Iwai S., Takio K., Hanaoka F. The XPV (xeroderma pigmentosum variant) gene encodes human DNA polymerase eta. Nature. 399:1999;700-704.
97. Masutani C., Araki M., Yamada A., Kusumoto R., Nogimori T., Maekawa T., Iwai S., Hanaoka F. Xeroderma pigmentosum variant (XP-V) correcting protein from HeLa cells has a thymine dimer bypass DNA polymerase activity. EMBO J. 18:1999;3491-3501.
98. Johnson R.E., Kondratick C.M., Prakash S., Prakash L. hRAD30 mutations in the variant form of xeroderma pigmentosum. Science. 285:1999;263-265.
99. Johnson R.E., Prakash S., Prakash L. Efficient bypass of a thymine-thymine dimer by yeast DNA polymerase, Poleta. Science. 283:1999;1001-1004.
100. Johnson R.E., Washington M.T., Prakash S., Prakash L. Fidelity of human DNA polymerase eta. J. Biol. Chem. 275:2000;7447-7450.
101. Johnson R.E., Washington M.T., Prakash S., Prakash L. Bridging the gap: a family of novel DNA polymerases that replicate faulty DNA. Proc. Natl. Acad. Sci. U.S.A. 96:1999;12224-12226.
102. Ogi T., Kato T. Jr., Kato T., Ohmori H. Mutation enhancement by DINB1, a mammalian homologue of the Escherichia coli mutagenesis protein dinB. Genes Cells. 4:1999;607-618.
103. Gerlach V.L., Aravind L., Gotway G., Schultz R.A., Koonin E.V., Friedberg E.C. Human and mouse homologs of Escherichia coli DinB (DNA polymerase IV), members of the UmuC/DinB superfamily. Proc. Natl. Acad. Sci. U.S.A. 96:1999;11922-11927.
104. Koffel-Schwartz N., Coin F., Veaute X., Fuchs R.P. Cellular strategies for accommodating replication-hindering adducts in DNA: control by the SOS response in Escherichia coli. Proc. Natl. Acad. Sci. U.S.A. 93:1996;7805-7810.
105. Napolitano R.L., Lambert I.B., Fuchs R.P. SOS factors involved in translesion synthesis. Proc. Natl. Acad. Sci. U.S.A. 94:1997;5733-5738.
106. Malia S.A., Vyas R.R., Basu A.K. Site-specific frame-shift mutagenesis by the 1-nitropyrene-DNA adduct N-(deoxyguanosin-8-y1)-1-aminopyrene located in the (CG)3 sequence: effects of SOS, proofreading, and mismatch repair. Biochemistry. 35:1996;4568-4577.
107. Rahman M.S., Humayun M.Z. SOS and UVM pathways have lesion-specific additive and competing effects on mutation fixation at replication-blocking DNA lesions. J. Bacteriol. 181:1999;1515-1523.
108. Humayun M.Z. SOS and Mayday: multiple inducible mutagenic pathways in Escherichia coli. Mol. Microbiol. 30:1998;905-910.
109. Palejwala V.A., Wang G.E., Murphy H.S., Humayun M.Z. Functional recA, lexA, umuD, umuC, polA, and polB genes are not required for the Escherichia coli UVM response. J. Bacteriol. 177:1995;6041-6048.
110. Malia S.A., Basu A.K. Mutagenic specificity of reductively activated 1-nitropyrene in Escherichia coli. Biochemistry. 34:1995;96-104.
111. Chaudhuri I., Essigmann J.M. 3-Methyladenine mutagenesis under conditions of SOS induction in Escherichia coli. Carcinogenesis. 12:1991;2283-2289.
112. Eckert K.A., Ingle C.A., Drinkwater N.R. N-ethyl-N-nitrosourea induces A:T to C:G transversion mutations as well as transition mutations in SOS-induced Escherichia coli. Carcinogenesis. 10:1989;2261-2267.
113. Naser L.J.N., Yarema K.J., Lippard S.J., Essigmann J.M. Mutagneicity and genotoxicity of the major DNA adduct of the antitumor drug cis-diamminedichloroplatinum(II). Biochemistry. 32:1993;982-988.
114. Burnouf D., Gauthier C., Chottard J.C., Fuchs R.P. Single d(ApG)/cis-diamminedichloroplatinum(II) adduct-induced mutagenesis in Escherichia coli. Proc. Natl. Acad. Sci. U.S.A. 87:1990;6087-6091.
115. Veaute X., Fuchs R.P. Greater susceptibility to mutations in lagging strand of DNA replication in Escherichia coli than in leading strand. Science. 261:1993;598-600.
116. Fijalkowska I.J., Jonczyk P., Tkaczyk M.M., Bialoskorska M., Schaaper R.M. Unequal fidelity of leading strand and lagging strand DNA replication on the Escherichia coli chromosome. Proc. Natl. Acad. Sci. U.S.A. 95:1998;10020-10025.
117. Radman M. DNA replication: one strand may be more equal. Proc. Natl. Acad. Sci. U.S.A. 95:1998;9718-9719.
118. Wagner J., Kamiya H., Fuchs R.P. Leading versus lagging strand mutagenesis induced by 7,8-dihydro-8-oxo-2′-deoxyguanosine in Escherichia coli. J. Mol. Biol. 265:1997;302-309.
119. Lavrukhin O.V., Lloyd R.S. 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. 58:1998;887-891.
120. Gibbs P.E., Kilbey B.J., Banerjee S.K., Lawrence C.W. The frequency and accuracy of replication past a thymine-thymine cyclobutane dimer are very different in Saccharomyces cerevisiae and Escherichia coli. J. Bacteriol. 175:1993;2607-2612.
121. Milhe C., Dhalluin C., Fuchs R.P., Lefevre J.F. NMR evidence of the stabilisation by the carcinogen N-2-acetylaminofluorene of a frameshift mutagenesis intermediate. Nucleic Acids Res. 22:1994;4646-4652.
122. A. Garcia, I.B. Lambert, R.P. Fuchs, DNA adduct-induced stabilization of slipped frameshift intermediates within repetitive sequences: implications for mutagenesis. Proc. Natl. Acad. Sci. U.S.A., 90, 5989-5993.
123. Loechler E.L. Adduct-induced base-shifts: a mechanism by which the adducts of bulky carcinogens might induce mutations. Biopolymers. 28:1989;909-927.
124. E.L. Loechler, M. Benasutti, A.K. Basu, C.L. Green, J.M. Essigmann, The role of carcinogen DNA adduct structure in the induction of mutations, Progress in Clinical and Biological Research, Vol. 340A, Mutation and the Environment, Part A: Basic Mechanisms, Wiley, New York, 1990, pp. 51-60, (Mendelsohn and Albertini).
125. Geacintov N.E., Cosman M., Hingerty B.E., Amin S., Broyde S., Patel D.J. NMR solution structures of stereoisomeric polycyclic aromatic carcinogen-DNA adducts: principles, patterns and diversity. Chem. Res. Toxicol. 10:1997;111-131.
126. Norman D., Abuaf P., Hingerty B.E., Live D., Grunberger D., Broyde S., Patel D.J. NMR and computational characterization of the N-(deoxyguanosin-8-yl)aminofluorene adduct [(AF)G] opposite adenosine in DNA: (AF)G[syn]. A[anti] pair formation and its pH dependence. Biochemistry. 28:1989;7462-7476.
127. Gu Z., Gorin A., Hingerty B.E., Broyde S., Patel D.J. Solution structures of aminofluorene [AF]-stacked conformers of the syn [AF]-C8-dG adduct positioned opposite dC or dA at a template-primer junction. Biochemistry. 38:1999;10855-10870.
128. 2-dG) of the potent environmental carcinogen benzo[a]pyrene.
129. McCann J., Choi E., Yamasaki E., Ames B.N. Detection of carcinogens in the Salmonella/microsome test: assay of 300 chemicals. Proc. Natl., Acad. Sci. U.S.A. 72:1975;5135-5139.
130. C.E. Searle (Ed.), Chemical Carcinogens, 2nd edn., American Chemical Society, Washington, DC, 1984, (ACS Monograph 182).
131. R. Montesano, H. Bartsch, H. Vainio, J. Wilbourn, H. Yamasaki (Eds.), Long-term and Short-term Assays for Carcinogens: A Critical Appraisal, International Agency for Research on Cancer, Lyon, France, 1986.
132. R.G. Harvey, Polycyclic Aromatic Hydrocarbons: Chemistry and Cancer, Cambridge Univ. Press, Cambridge, UK, 1991.
133. B. Singer, D. Grunberger, Molecular Biology of Mutagens and Carcinogens, Plenum, New York, 1983.
134. Miller J.H. Mutational specificity in bacteria. Annu. Rev. Genet. 17:1983;215-238.
135. R.G. Harvey, Polycyclic Aromatic Hydrocarbons: Chemistry and Cancer, Cambridge Univ. Press, Cambridge, UK, 1991.
136. Phillips D.H. Fifty years of benzo[a]pyrene. Nature. 303:1983;468-472.
137. B. Singer, D. Grunberger, Molecular Biology of Mutagens and Carcinogens, Plenum, New York, 1983.
138. Conney A.H. Induction of microsomal enzymes by foreign chemicals and carcinogens by polycyclic aromatic hydrocarbons. Cancer Res. 42:1982;4875-4917.
139. A. Dipple, Polycyclic aromatic hydrocarbon carcinogens, in: R.G. Harvey (Ed.), Polycyclic Aromatic Hydrocarbons and Carcinogenesis, American Chemical Society Press, Washington, DC, 1985, pp. 1-17.
140. P.W. Jones, Polynuclear aromatic hydrocarbons, in: M.G. Bowman (Ed.), Handbook of Carcinogens and Hazardous Substances, Marcel Dekker, New York, 1982, pp. 5723-639.
141. P. Grasso, Carcinogens in food, in: C.E. Searle (Ed.), Chemical Carcinogens 2nd edn., Amreican Chemical Society Press, Washington, DC, 1984, pp. 1205-1239, ACS Monograph 182.
142. Eisenstadt E., Warren A.J., Porter J., Atkins D., Miller J.H. Carcinogenic epoxides of benzo[a]pyrene and cyclopenta[cd]pyrene induce base substitutions via specific transversions. Proc. Natl. Acad. Sci. U.S.A. 82:1982;1945-1949.
143. Bernelot-Moens C., Glickman B.W., Gordon A.J.E. Induction of specific frameshift and base substitution events by benzo[a]pyrene diol epoxide in excision-repair-deficient Escherichia coli. Carcinogenesis. 11:1990;781-785.
144. Yang J.L., Maher V.M., McCormick J.J. Kinds of mutations formed when a human shuttle vector containing adducts of (±)-7beta, 8alpha-dihydroxy-9alpha, 10alpha-epoxy-7,8,9,10-dihydrobenzo[a]pyrene replicates in human cells. Proc. Natl. Acad. Sci. U.S.A. 84:1987;3787-3791.
145. Yang J.-L., Chen R.-H., Maher V.M., McCormick J.J. Kinds and locations of mutations induced by (±)-7beta,8alpha-dihydroxy-9alpha,10alpha-epoxy-7,8,9,10-dihydrobenzo[a] pyrene in the coding region of the hypoxanthine (guanine) phosphoribosyltransferase gene in diploid human fibroblasts. Carcinogenesis. 12:1990;71-75.
146. Carothers A.M., Grunberger D. DNA base changes in benzo[a]pyrene diol epoxide-induced dihydrofolate reductase mutants of Chinese hampster ovary cells. Carcinogenesis. 11:1990;189-192.
147. Nicol C.J., Harrison M.L., Laposa R.R., Gimelshtein I.L., Wells P.G. A teratologic suppressor role for p53 in benzo[a]pyrene-treated transgenic-deficient mice. Nature Genetics. 10:1995;181-187.
148. Chakravarti D., Pelling J., Cavalieri E.L., Rogan E.G. Relating aromatic hydrocarbon-induced DNA adducts and the c-H-ras mutations in mouse skin papillomas: the role of apurinic sites. Proc. Natl. Acad. Sci. U.S.A. 92:1995;10422-10426.
149. Chen L., Devanesan R., Higginbotham S., Ariese F., Jankowiak R., Small G.J., Rogan E.G., Cavalieri E. Expanded analysis of benzo[a]pyrene-DNA adducts formed in vitro and in mouse skin: their significance in tumor initiation. Chem. Res. Toxicol. 9:1996;897-903.
150. Balmain A., Brown K. Oncogene activation in chemical carcinogenesis. Adv. Cancer Res. 51:1988;147-182.
151. Ruggeri B.A., Bauer B., Zhang S.-Y., Klein-Szanto A.J.P. Murine squamous cell carcinoma cell lines produced by a complete carcinogenesis protocol with benzo[a]pyrene exhibit characteristic p53 mutations and the absence of H-ras and cyl1/cyclin D1 abnormalities. Carcinogenesis. 15:1994;1619-6113.
152. M. Hall, P.L. Grover, in: G.S. Cooper, P.L. Grover (Eds.), Handbook of Experimental Pharmacology, Chemical Carcinogenesis and Mutagenesis vol. 94/1 Springer, Heidelberg, 1990, pp. 327-372.
153. Cheng S.C., Hilton B.D., Roman J.M., Dipple A. DNA adducts from carcinogenic and noncarcinogenic enantiomers of benzo[a]pyrene dihydrodiol epoxide. Chem. Res. Toxicol. 2:1989;334-340.
154. Sayer J.M., Chadha A., Agarwal H.S.K., Yeh H.J.C., Yagi H., Jerina D.M. Covalent nucleoside adducts of benzo[a]pyrene 7,8-diol 9,10-epoxides: structural reinvestigation and characterization of a novel adenosine adduct on the ribose moiety. J. Org. Chem. 56:1991;20-29.
155. Phillips D.H., Hewer A., Grover P.L. Aberrant activation of benzo[a]pyrene in cultured rat mammary cells in vitro and following direct application to rat mammary glands in vivo. Cancer Res. 45:1985;4167-4174.
156. Marnett L.J. Peroxyl free radicals: potential mediators of tumor initiation and promotion. Carcinogenesis. 8:1987;1365-1373.
157. Devanesan P.D., RamaKrishna N.V.S., Todorovic R., Rogan E.G., Cavalieri E.L., Jeong H., Jankowiak R., Small G.J. Identification and quantitation of benzo[a]pyrene-DNA adducts formed by rat liver microsomes. Chem. Res. Toxicol. 5:1992;302-309.
158. Todorovic R., Ariese F., Devanesan R., Jankowiak R., Small G.J., Rogan E.G., Cavalieri E. Determination of benzo[a]pyrene- and 7,12-dimethylbenz[a]anthracene-DNA adducts formed in rat mammary glands. Chem. Res. Toxicol. 10:1997;941-947.
159. Flowers-Geary L., Bleczinski W., Harvey R.G., Penning T.M. Cytotoxicity and mutagenicity of polycyclic aromatic hydrocarbon o-quinone produced by dihydrodiol dehydrogenase. Chem.-Biol. Interact. 99:1996;55-72.
160. Rodriguez H., Loechler E.L. Are base substitution and frameshift mutagenesis pathways interrelated? An analysis based upon studies of mutagenesis by the (+)-anti diol epoxide of benzo[a]pyrene. Mutat. Res. 326:1995;29-37.
161. 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. 34:1995;13545-13553.
162. Hanrahan C.J., Bacolod M.D., Vyas R.R., Liu T., Geacintoc N.E., Loechler E.L., Basu A.K. Sequence specific mutagenesis of the major (+)-anti-benzo[a]pyrene diol epoxide-DNA adduct at a mutational horspot in vitro and in Escherichia coli cells. Chem. Res. Toxicol. 10:1997;369-377.
163. 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. 36:1997;10256-10261.
164. Gill R.D., Min Z., Cortez C., Harvey R.G., Loechler E.L., DiGiovanni J. Construction of Escherichia coli vectors containing deoxyadenosine and deoxyguanosine adducts from (+)-anti-dibenz[a,j]anthrcene-diol-epoxide at a defined site. Chem. Res. Toxicol. 6:1993;681-689.
165. Gill R.D., Rodriguez H., Cortez C., Harvey R.G., Loechler E.L., DiGiovanni J. Mutagenic specificity of the (+)-anti-diol epoxide of dibenz[a,j]anthracene in the supF gene of an Escherichia coli plasmid. Mol. Carcinog. 8:1993;145-154.
166. Min Z., Gill R.G., Cortez C., Harvey R.G., Loechler E.L., DiGiovanni J. Targeted A→T, and G→T mutations induced by site-speific deoxyadenosine and deoxyguanosine adducts, respectively, fromthe (+)-anti-diol-epoxide of dibenz[a,j]anthracene in M13mp7L2. Biochemistry. 35:1996;4128-4138.
167. Wei S.-J.C., Chang R.L., Wong C.-Q., Bhachech N., Cui X.X., Hennig E., Yagi H., Sayer J.M., Jerina D.M., Preston B.D., Conney A.H. Dose-dependent differences in the profile of mutations induced by an ultimate carcinogen from benzo[a]pyrene. Proc. Natl. Acad. Sci. U.S.A. 88:1991;11227-11230.
168. Wei S.-J.C., Chang R.L., Bhachech N., Cui X.X., Merkler K.A., Wong C.Q., Hennig E., Yagi H., Jerina D.M., Conney A.H. Dose-dependent differences in the profile of mutations induced (+)-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 hampster V79 cells. Cancer Res. 53:1993;3294-3301.
169. Wei S.J., Chang R.L., Hennig E., Cui X.X., Merkler K.A., Wong C.Q., Yagi H., Jerina D.M., Conney A.H. Mutagenic selectivity at the HPRT locus in V-79 cells: comparison of mutations caused by bay-region benzo[a]pyrne 7,8-diol-9,10-opxide enantiomers with high and low carcinmogenic activity. Carcinogenesis. 15:1995;1729-1735.
170. D'Ayala M., Cui X.X., Lu Y.P., Yagi H., Jerina D.M., Conney A.H., Wei S.J. Lack of dose dependence in mutation profile induced by (+)-7R,8S-dihydroxy-9S,10R-spoxy-7,8,9,10-tetrahydrobenzo[a]-pyrene [(+)-BPDE] at the hprt gene in repair deficient Chinese hampster V-H1 cells. Proc. Am. Assoc. Cancer Res. 39:1998;639.
171. Wei S.J., Chang R.L., Wong C.Q., Cui X.X., Dandamudi N., Lu Y.P., Merkler K.A., Sayer J.M., Conney A.H., Jerina D.M. The ratio of deoxyadenosine to deoxyguanosine adducts formed by (+)-(7R,8S,9S,10R)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene in purified calf thymus DNA and DNA in V-79 cells is independent of dose. Int. J. Oncol. 14:1999;509-513.
172. Drouin E., Loechler E.L. Mutagenesis by the (+)-anti diol epoxide benzo[a]pyrene does not significantly involve AP-sites: evidence that the complexity of the mutational spectra is due to adduct conformational polymorphism. Biochemistry. 32:1993;6555-6562.
173. Drouin E., Loechler E.L. The major adduct of the (+)-anti diol epoxide benzo[a]pyrene can be unstable in double stranded DNA. Biochemistry. 34:1995;2251-2259.
174. Rodriguez H., Loechler E.L. Are base substitution and frameshift mutagenesis pathways interrelated? An analysis based upon studies of mutagenesis by the (+)-anti diol epoxide of benzo[a]pyrene. Mutat. Res. 326:1995;29-37.
175. Joseph P., Jaiswal A.K. NAD(P)H:quinone oxidoreductase 1 reduces the mutagenicity of DNA caused by NADPH:P450 reductase-activated metabolites of benzo[a]pyrene quinones. Br. J. Cancer. 77:1998;709-719.
176. Kapitulnik J., Wislocki P.G., Levin W., Yagi H., Jerina D.M., Conney A.H. Tumorigenicity studies with diol-epoxides of benzo(a)pyrene which indicate that (±)-trans-7beta,8alpha-dihydroxy-9alpha,10alpha-epoxy-7,8,9,10- tetrahydrobenzo(a)pyrene is an ultimate carcinogen in newborn mice. Cancer Res. 38:1978;354-358.
177. Wood A.W., Sayer J.M., Newmark H.L., Yagi H., Michaud D.P., Jerina D.M., Conney A.H. Mechanism of the inhibition of mutagenicity of a benzo[a]pyrene 7,8-diol 9,10-epoxide by riboflavin 5′-phosphate. Proc. Natl. Acad. Sci. U.S.A. 79:1982;5122-5126.
178. Wu D.Y., Wallace R.B. The ligation amplification reaction (LAR)-amplification of specific DNA sequences using sequential rounds of template-dependent ligation. Genomics. 4:1989;560-569.
179. Wu D.Y., Wallace R.B. Specificity of the nick-closing activity of bacteriophage T4 DNA ligase. Gene. 76:1989;245-254.
180. Barany F. The ligase chain reaction in a PCR world. PCR Methods Appl. 1:1991;15-16.
181. Landgren U. Ligation-based DNA diagnostics. BioEssays. 15:1993;761-765.
182. Piskur J., Rupprecht A. Aggregated DNA in ethanol solution. FEBS Lett. 375:1995;174-178.
183. Lerman L.S. A transition to a compact form of DNA in polymer solutions. Proc. Natl. Acad. Sci. U.S.A. 68:1971;1886-1890.
184. 6-methylguanine can adopt multiple conformations. Proc. Natl. Acad. Sci. U.S.A. 90:1993;3983-3987.
185. 6-methylguanine: the syn and anti-conformers can be of similar energies in duplex DNA as estimated by molecular modeling techniques. Carcinogenesis. 12:1991;1693-1699.
186. 6meG-C-G) duplex. Biochemistry. 25:1986;1036-1042.
187. 6etG.T pairing in dodecanucleotide duplexes. Biochemistry. 28:1989;6170-6181.
188. Leonard G.A., Thomson J., Watson W.P., Brown T. High-resolution structure of a mutagenic lesion in DNA. Proc. Natl. Acad. Sci. U.S.A. 87:1990;9573-9576.
189. Ripley L.S. Predictability of mutant sequences. Relationships between mutational mechanisms and mutant specificity. Ann. N. Y. Acad. Sci. 870:1999;159-172.
190. Papanicolaou C., Ripley L.S. An in vitro approach to identifying specificity determinants of mutagenesis mediated by DNA misalignments. J. Mol. Biol. 221:1991;805-821.
191. Ripley L.S. Frameshift mutation: determinants of specificity. Annu. Rev. Genet. 24:1990;189-213.
192. de Boer J.G., Ripley L.S. Demonstration of the production of frameshift and base-substitution mutations by quasipalindromic DNA sequences. Proc. Natl. Acad. Sci. U.S.A. 81:1984;5528-5531.
193. Ripley L.S. Model for the participation of quasi-palindromic DNA sequences in frameshift mutation. Proc. Natl. Acad. Sci. U.S.A. 79:1982;4128-4132.
194. Bebenek K., Kunkel T.A. Frameshift errors initiated by nucleotide misincorporation. Proc. Natl. Acad. Sci. U.S.A. 87:1990;4946-4950.
195. Boosalis M.S., Mosbaugh D.W., Hamatake R., Sugino A., Kunkel T.A., Goodman M.F. Kinetic analysis of base substitution mutagenesis by transient misalignment of DNA and by miscoding. J. Biol. Chem. 264:1989;11360-11366.
196. Kunkel T.A., Soni A. Mutagenesis by transient misalignment. J. Biol. Chem. 263:1988;14784-14789.
197. Kunkel T.A., Alexander P.S. The base substitution fidelity of eucaryotic DNA polymerases. Mispairing frequencies, site preferences, insertion preferences, and base substitution by dislocation. J. Biol. Chem. 261:1986;160-166.
198. Geacintov N.E. Is intercalation a critical factor in the covalent binding of mutagenic and tumorigenic polycyclic aromatic diol epoxides to DNA? Carcinogenesis. 7:1986;759-766.
199. Loechler E.L. Molecular modeling in mutagenesis and carcinogenesis. Methods in Enzymology, Molecular Design and Modeling: Concepts and Applications. vol. 203:1991;458-476.
200. Kozack R., Loechler E.L. Molecular modeling of the conformational complexity of (+)-anti-B[a]PDE-adducted DNA using simulated annealing. Carcinogenesis. 18:1997;1585-1593.
201. 2-dG) in the eight conformations and the five DNA sequences most relevant to base substitution mutagenesis. Carcinogenesis. 20:1999;85-94.
202. 2-dG) causes G→T vs. G→A mutations based upon a correlation between mutagenesis and molecular modeling results. Carcinogenesis. 20:1999;95-104.
203. Eckel L.M., Krugh T.R. 2-Aminofluorene modified DNA duplex exists in two interchangeable conformations. Nat. Struct. Biol. 1:1994;89-94.
204. Eckel L.M., Krugh T.R. Structural characterization of two interchangeable conformations of a 2-aminofluorene-modified DNA oligomer by NMR and energy minimization. Biochemistry. 33:1994;13611-13624.
205. Withka J.M., Wilde J.A., Bolton P.H., Mazumder A., Gerlt J.A. Characterization of conformational features of DNA heteroduplexes containing aldehydic abasic sites. Biochemistry. 30:1991;9931-9940.
206. Wilde J.A., Bolton P.H., Mazumber A., Manoharan M., Gerlt J.A. J. Am. Chem. Soc. 111:1989;1894-1896.
207. Lawrence C.W., Borden A., Banerjee S.K., LeClerc J.E. Mutation frequency and spectrum resulting from a single abasic site in a single-stranded vector. Nucleic Acids Res. 25:1990;2153-2157.
208. Rodriguez H., Bhatt U., Snow E.T., Loechler E.L. An Escherichia coli plamsid-based, mutational system in which supF mutants are selectable: insertion elements dominate the spontaneous spectra. Mutat. Res. 270:1992;219-231.