Molecular mechanisms of mutagenesis by aromatic amines and amides

Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

Volumn 376, Issue 1-2, 1997, Pages 71-78

  Shibutani, Shinya ^a   Grollman, Arthur P ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

Acetylaminofluorene; Aminofluorene; Arylamine; Frameshift; Mutagenesis; Translesional synthesis

Indexed keywords

AROMATIC AMIDE; AROMATIC AMINE; DNA POLYMERASE; N (2 FLUORENYL)ACETAMIDE;

ARTICLE; DNA ADDUCT; FRAMESHIFT MUTATION; MOLECULAR GENETICS; MUTAGENESIS; MUTAGENICITY; NONHUMAN; PRIORITY JOURNAL;

2-ACETYLAMINOFLUORENE; ANIMALS; CELLS, CULTURED; COS CELLS; DNA ADDUCTS; DNA REPLICATION; DNA-DIRECTED DNA POLYMERASE; MUTAGENESIS; MUTAGENICITY TESTS; SEQUENCE DELETION;

BACTERIA (MICROORGANISMS); MAMMALIA;

EID: 0030995725     PISSN: 00275107     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0027-5107(97)00027-4     Document Type: Article

References (41)

1. Bebenek, K. and T.A. Kunkel (1990) Frameshift errors initiated by nucleotide misincorporation, Proc. Natl. Acad. Sci. USA 87, 4946-4950.
2. 6-substituted deoxyguanosine adduct of 1-naphthylamine in the DNA double helix, Chem.-Biol. Interact., 22, 329-339.
3. Beland, F.A., K.L. Dooley and C.D. Jackson (1982) Persistence of DNA adducts in rat liver and kidney after multiple doses of the carcinogen N-hydroxy-2-acetylaminofluorene, Cancer Res., 42, 1348-1354.
4. Beland, F.A., D.T. Beranek, K.L. Dooley, R.H. Heflich and F.F. Kadlubar (1983) Arylamine-DNA adducts in vitro and in vivo: their role in bacterial mutagenesis and urinary bladder carcinogenesis, Environ. Health Perspect., 49, 125-134.
5. Beland, F.A. and F.F. Kadlubar (1985) Formation and persistence of arylamine DNA adducts in vivo, Environ. Health Perspect., 62, 19-30.
6. Burnouf, D., P. Koehl and R.P.P. Fuchs (1989) Single adduct mutagenesis: strong effect of the position of a single acetylaminofluorene adduct within a mutation hot spot, Proc. Natl. Acad. Sci. USA, 86, 4147-4151.
7. Clark, J.M., C.M. Joyce and G.P. Beardsley (1987) Novel blunt-end addition reactions catalyzed by DNA polymerase I of Escherichia coli, J. Mol. Biol., 198, 123-127.
8. Cotton, R.G.H. (1989) Detection of single base changes in nucleic acids, Biochem. J., 263, 1-10.
9. Fowler, R.G., G.E. Degnen and E.C. Cox (1974) Mutational specificity of a conditional Escherichia coli mutator, mutD5, Mol. Gen. Genet., 133, 179-191.
10. Gupta, P.K., D.L. Johnson, T.M. Reid, M.-S. Lee, L.J. Romano and C.M. King (1989) Mutagenesis by single site-specific arylamine-DNA adducts, J. Biol. Chem., 264, 20120-20130.
11. Howard, P.C., D.A. Casciano, F.A. Beland and J.G. Shaddock Jr. (1981) The binding of N-hydroxy-2-acetylaminofluorene to DNA and repair of the adducts in primary rat hepatocyte cultures, Carcinogenesis, 2, 97-102.
12. Kriek, E. (1972) Persistent binding of a new reaction product of the carcinogen N-hydroxy-N-2-acetylaminofluorene with guanine in rat liver DNA in vivo, Cancer Res., 32, 2042-2048.
13. +, Carcinogenesis, 1, 459-468.
14. Kunkel, T.A. and A. Soni (1988) Mutagenesis by transient misalignment, J. Biol. Chem., 263, 14784-14789.
15. Kunkel, T.A. (1990) Misalignment-mediated DNA synthesis errors, Biochemistry, 29, 8003-8011.
16. Lambert, I.B., R.L. Napolitano and R.P.P. Fuchs (1992) Carcinogen-induced frameshift mutagenesis in repetitive sequences, Proc. Natl. Acad. Sci. USA, 89, 1310-1314.
17. Madzak, C. and A. Sarasin (1991) Conversion of a single-stranded simian virus 40 (SV40)-based shuttle vector to its double-stranded form does not require the SV40 T-antigen in monkey cells, J. Gen. Virol., 72, 3091-3093.
18. Maxam, A.M. and Gilbert, W. (1977) A new method for sequencing DNA, Proc. Natl. Acad. Sci. USA, 74, 560-564.
19. Mendelman, L.V., B.S. Boosalis, J. Petruska and M.F. Goodman (1989) Nearest neighbor influences on DNA polymerase insertion fidelity, J. Biol. Chem., 264, 14415-14423.
20. Mendelman, L.V., J. Petruska and M.F. Goodman (1990) Base mispair extension kinetics, J. Biol. Chem., 265, 2338-2346.
21. Michaels, M.L., T.M. Reid, C.M. King and L.J. Romano (1991) Accurate in vitro translesion synthesis by Escherichia coli DNA polymerase I (large fragment) on a site-specific, aminofluorene-modified oligonucleotide, Carcinogenesis, 12, 1641-1646.
22. Moriya, M., M. Takeshita, F. Johnson, K. Peden, S. Will and A.P. Grollman (1988) Targeted mutations induced by a single acetylaminofluorene DNA adduct in mammalian cells and bacteria, Proc. Natl. Acad. Sci. USA, 85, 1586-1589.
23. Moriya, M., C. Ou, V. Bodepudi, F. Johnson, M. Takeshita and A.P. Grollman (1991) Site specific mutagenesis using a gapped duplex vector: a study of translesion synthesis past 8-oxodeoxyguanosione in E. coli, Mutation Res., 254, 281-288.
24. Moriya, M. (1993) Single strand shuttle phagemid for mutagenesis studies in mammalian cells: 8-oxoguanine in DNA induces targeted G:C → T:A transversion in simian kidney cells, Proc. Natl. Acad. Sci. USA, 90, 1122-1126.
25. Rio, P., S. Bazgar and M. Long (1982) Detection of N-hydroxy-2-acetylaminofluorene-DNA adducts in rat liver measured by radioimmuno-assay, Carcinogenesis, 3, 225-227.
26. Sanger, F., Nicklen, S. and Coulson, A.R. (1977) DNA sequencing with chain-terminating inhibitors, Proc. Natl. Acad. Sci. USA, 74, 5463-5467.
27. Shibutani, S., R.G. Gentles, C.R. Iden and F. Johnson (1990) Facile aerial oxidation of the DNA-base adduct N-(2′-deoxyguanosin-8-yl)-2-aminofluorene[dG(C8)AF]. J. Am. Chem. Soc. 112, 5667-5668.
28. 2-AAF and oxidation products of dG-C8-AF. Carcinogenesis, 12, 813-818.
29. Shibutani, S., M. Takeshita and A.P. Grollman (1991b) Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG, Nature, 349, 431-434.
30. 2-yl)-2-(acetylamino)fluorene, Chem. Res. Toxicol., 6, 819-824.
31. Shibutani, S. and A.P. Grollman (1993b) On the mechanism of frameshift (deletion) mutagenesis in vitro, J. Biol. Chem., 268, 11703-11710.
32. Shibutani, S. (1993) Quantitation of base substitutions and deletions induced by chemical mutagens during DNA synthesis in vitro, Chem. Res. Toxicol., 6, 625-629.
33. Shibutani, S. (1994) Mutagenic specificity of acetylaminofluorene-derived DNA adducts in vitro, in K. Hemminki, A. Dipple, D.E. Shuker, F.F. Kadlubar, D. Segerback and H. Bartsch (Eds.), DNA Adducts: Carcinogens and Mutagenic Agents: Chemistry, Identification, and Biological Significance, IARC Scientific Publications No. 125, Lyon, France, pp. 457-462.
34. 4-etheno-2′-deoxycytidine in reactions catalyzed by mammalian DNA polymerases, Biochemistry, 35, 14992-14998.
35. Streisinger, G., Y. Okada, J. Emrich, J. Newton, A. Tsugita, E. Terzaghi and M. Inouye (1966) Frameshift mutations and the genetic code, Cold Spring Harbor Symp. Quant. Biol., 31, 77-84.
36. Streisinger, G. and J.E. Owen (1985) Mechanisms of spontaneous and induced frameshift mutation in Bacteriophage T4, Genetics, 109, 633-659.
37. Visser, A. and J.G. Westra (1981) Partial persistency of 2-aminofluorene and N-acetyl-2-aminofluorene in rat liver DNA, Carcinogenesis, 2, 737-740.
38. Wallace, R.B., M.J. Johnson, T. Hirose, T. Miyake, E.H. Hawashima and K. Itakura (1981) The use of synthetic oligonucleotides as hybridization probes. II. Hybridization of oligonucleotides of mixed sequence of rabbit β-globin DNA, Nucleic Acids Res., 9, 879-894.
39. Wang, T.S.-F. (1991) Eukaryotic DNA polymerases, Annu. Rev. Biochem., 60, 513-552.
40. Westra, J.G., E. Kriek and H. Hittenhausen (1976) Identification of the persistently bound form of the carcinogen N-acetyl-2-aminofluorene to rat liver DNA in vivo, Chem.-Biol. Interact., 15, 149-164.
41. 2 guanosine adducts of N-acetyl-2-aminofluorene by single strand-specific endonucleases, Cancer Res., 37, 3756-3760.