Mutagenicity of aminonitrophenol compounds in Salmonella typhimurium: a study of structural-activity relationships

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Abstract
In our studies of structure-activity relationships, four aminonitrophenol isomers and eleven derivatives of 3-amino-4-nitrophenol and 4-amino-3-nitrophenol were tested for their ability to induce mutations in Salmonella typhimurium strains TA1535, TA100, TA1537, TA1538 and TA98. In the presence of an Aroclor-1254-induced rat-liver microsomal activation system (S9mix), 4-N-β-hydroxyethylamino-3-nitroanisole and (4-amino-3-nitro) phenoxyethanol were mutagenic in several of these strains. The compounds 3-amino-4-nitrophenol, 3-N-methylamino-4-nitrophenol, 3-N-β-hydroxyethylamino-4-nitrophenol, 3-amino-4-nitroanisole, 3-N-methylamino-4-nitroanisole, 3-N-β-hydroxyethylamino-4-nitroanisole, (3-amino-4-nitro)phenoxyethanol, (3-methylamino-4-nitro)phenoxyethanol, (3-N-β-hydroxyethylamino-4-nitro)phenoxyethanol, 4-amino-3-nitrophenol and 4-N-β-hydroxyethylamino-3-nitrophenol were inactive, both in the presence and in the absence of S9 mix. In contrast to the results with 3-amino-4-nitrophenol and 4-amino-3-nitrophenol, which were negative, the isomers 2-amino-4-nitrophenol and 2-amino-5-nitrophenol were found to be mutagenic. These results on mutagenic and non-mutagenic aminonitrophenols and their derivatives suggest that the occurrence of mutagenic activity among these compounds depends on the nature of the substituent chemical groups and their position in the molecular structure of the compounds. Aminonitriphenols: relation structure-activité