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

Molecular toxicology Pub Date : 1989-01-01
N M Trieff, G L Biagi, V M Sadagopa Ramanujam, T H Connor, G Cantelli-Forti, M C Guerra, H Bunce, M S Legator
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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 and 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.

鼠伤寒沙门菌TA98和TA100中芳香胺和乙酰胺的定量构效关系研究。
从Aroclor 1254诱导的大鼠肝脏中加入S9,对鼠伤寒沙门菌菌株TA98(移框)和TA100(碱基对)进行了一系列19种芳香胺的诱变性测定。采用多元回归分析的定量构效关系(QSAR)研究指出了三个因素对致突变性的影响:亲脂性、胺基的位置、是否游离或乙酰化,分别用log P和两个指标变量I1和I2表示。多元回归方程分别解释了TA98和TA100中对数诱变性方差的78%和88%。首先,诱变性随着亲脂性的增加而增加。另一方面,与非邻位异构体相比,当胺或对乙酰氨基位置与接合点邻位时,由于其生物转化中的空间位阻,致突变性降低。它也会因胺基的乙酰化而降低,可能是因为在胺基氧化成-NHOH之前,乙酰基需要先被分离。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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