PMID: 7026224Jan 1, 1981Paper

Structural basis of the mutagenicity in bacteria of nitrated naphthalene and derivatives

Environmental Mutagenesis
E McCoyR Mermelstein

Abstract

While 2-nitronaphthalene was a weak direct-acting base-substitution mutagen (1.4 revertants/nanomole) for Salmonella typhimurium, the analogous nitronaphthalic acid anhydride and imides were moderate frameshift mutagens (approximately 20 rev/nanomole in strain TA98). Although imide derivatives are efficient DNA intercalators, mutagenicity data indicate that the bulk of the frameshift activity is derived from adduct formation between hydroxylamine intermediates and DNA. The low level of frameshift activity (approximately 8% of total) resulting from simple intercalation (measured in strain TA 1537) is not dependent upon reduction of the nitro function. Evidence is presented that suggests that the reduction of the nitro function to the corresponding hydroxylamine might not involve a free nitroso intermediate. The introduction of a second nitrofunction into nitronaphthalenes results in great positional effects of the various isomers on mutagenic activity and specificity.

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Citations

May 1, 1984·Mutation Research·G Klopman, H S Rosenkranz
Jan 1, 1991·Mutation Research·B G BoyesR Stapley
Aug 24, 2006·International Journal of Phytoremediation·Christopher F HoehamerKarl Erik L Eriksson
Jan 1, 1983·Drug and Chemical Toxicology·W E White, S G Rock
Apr 29, 2008·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·R R DihlH H R de Andrade
Jun 15, 2014·Archives of Biochemistry and Biophysics·Hilary GroomP David Josephy
Oct 1, 1984·Journal of Applied Toxicology : JAT·D E JohnsonH H Cornish
Jan 1, 1991·Environmental and Molecular Mutagenesis·V Mersch-SundermannF Wintermann
Jan 1, 1986·Critical Reviews in Toxicology·H Tokiwa, Y Ohnishi
Nov 1, 1982·Mutation Research·V W Mayer
Dec 11, 2014·Journal of Natural Products·Silvia Di GiacomoAntonella Di Sotto

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