Mechanisms of action of carcinogenic aromatic amines: an investigation using mutagenesis in bacteria

Chemico-biological Interactions
J D ScribnerN K Scribner

Abstract

The mutagenicities of groups of N-acetoxy-N-arylacetamides, nitroarenes, arylamides and arylamines were determined in the Salmonella typhimurium tester stains TA98, TA1538, TA100, TA1535 and TA1537. Three broad classes of mutagenic activity were found, interpreted as follows: class A, including 2-naphthylamine, produced essentially only base-pair substitution without induction of error-prone repair; class B, including 4-aminobiphenyl, caused consideration induction of error-prone repair, accompanied by a lower level of frame shifting; class C, including N-acetoxy-2-acetamidofluorene, produced high levels of frame shifting, with some induction of error-prone repair. Correlation of these results with known reactions of certain aromatic amine derivatives with nucleosides and nucleic acids, and with molecular orbital calculations, suggests that the effect of class A is produced by small aromatic groups attached to extranuclear heteroatoms in DNA bases, the effect of class B is caused by large aromatic groups attached to extranuclear heteroatoms or by arylamines attached to C-8 of guanine, while the effect of class C is caused by arylamides attached to C-8 of guanine, probably rotating into the helix, as proposed by others. The data...Continue Reading

References

Jun 1, 1979·Chemico-biological Interactions·N K Scribner, J D Scribner
Dec 1, 1975·Proceedings of the National Academy of Sciences of the United States of America·J McCannB N Ames
Mar 1, 1973·Proceedings of the National Academy of Sciences of the United States of America·B N AmesW E Durston

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Citations

Sep 1, 1982·Archives of Toxicology·B S Bock-HennigK W Bock
May 1, 1984·Mutation Research·G Klopman, H S Rosenkranz
Nov 1, 1982·Mutation Research·V W Mayer
Dec 1, 1981·Mutation Research·E J LaVoieD Hoffmann
Aug 1, 1985·Mutation Research·T SatoT Ishikawa
Jul 1, 1985·Chemico-biological Interactions·Y TsurutaP J O'Brien
Oct 15, 1982·Biochemical and Biophysical Research Communications·E C McCoyH S Rosenkranz
Oct 15, 1982·Biochemical and Biophysical Research Communications·F E Evans, D W Miller
Aug 26, 2014·International Archives of Occupational and Environmental Health·Kimiko TomiokaNorio Kurumatani
Jan 1, 1982·Journal of Environmental Science and Health. Part. B, Pesticides, Food Contaminants, and Agricultural Wastes·W M Draper, J C Street
Jan 1, 1985·Teratogenesis, Carcinogenesis, and Mutagenesis·G L White, R H Heflich
Jan 1, 1981·Environmental Mutagenesis·E C McCoyR Mermelstein
Jan 1, 1988·Environmental and Molecular Mutagenesis·R H HeflichF A Beland
May 16, 2018·Journal of Chromatographic Science·Shubo DongDeju Ye
May 1, 1982·Chemico-biological Interactions·K B LipkowitzF A Beland
Sep 6, 2012·Chemical Research in Toxicology·Igor ShamovskyPeter Sjö
Jun 21, 2018·Journal of Chemical Information and Modeling·Ryan W KungStacey D Wetmore

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