Aromatic amines and acetamides in Salmonella typhimurium TA98 and TA100: A quantitative structure-activity relation study

N. M. Trieff, G. L. Biagi, V. M.S. Ramanujam, T. H. Connor, G. Cante lli-Forti, M. C. Guerra, H. Bunce, M. S. Legator

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27 Scopus citations

Abstract

The mutagenicity of a series of 19 aromatic amines had been previously measured in Salmonella typhimurium strains TA98 (frame-shift) and TA100 (base-pair) with the addition of S9 from Aroclor 1254-induced rat liver. A quantitative structure-activity relation (QSAR) study using multiple regression analysis points out the influence of three factors on mutagenicity: Lipophilic character, position of the amine group, and whether it is free or acetylated, as expressed by log P and two indicator variables I1 and I2, respectively. The multiple regression equations explain 78 and 88% of the variance in log mutagenicity in TA98 en TA100, respectively. First of all, mutagenicity was shown to increase with lipophilicity. On the other hand, mutagenicity is reduced when the amine or acetamido position is ortho to the juncture because of steric hindrance in its biotransformation compared with a non-ortho isomer. It is decreased also by the acetylation of the amine group, probably because the acetyl group needs to be first split off prior to oxidation of the amine group to -NHOH.

Original languageEnglish (US)
Pages (from-to)53-65
Number of pages13
JournalMolecular Toxicology
Volume2
Issue number1
StatePublished - Dec 1 1989

ASJC Scopus subject areas

  • Toxicology

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    Trieff, N. M., Biagi, G. L., Ramanujam, V. M. S., Connor, T. H., Cante lli-Forti, G., Guerra, M. C., Bunce, H., & Legator, M. S. (1989). Aromatic amines and acetamides in Salmonella typhimurium TA98 and TA100: A quantitative structure-activity relation study. Molecular Toxicology, 2(1), 53-65.