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Correlations of Nitrenium Ion Selectivities with Quantitative Mutagenicity and Carcinogenicity of the Corresponding Amines

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journal contribution
posted on 14.11.2002, 00:00 by Michael Novak, Sridharan Rajagopal
There is a correlation (radj2 = 0.5491−0.6338) of quantitative mutagenicity, log m, for a series of heterocyclic (HCAs) and carbocyclic (AAs) aromatic amines in Salmonella typhimurium TA 98 (18 amines) and TA 100 (15 amines) vs log S, the log of the azide/solvent selectivity of the corresponding nitrenium ion. Monocyclic aromatic amines, MAAs, are less mutagenic than other amines of similar log S. Multiple variable linear regression analysis led to a two parameter regression model, significant at the 95% confidence level for both variables, that includes log S and a ring index variable, Irings, that is 0 for MAAs and 1 for all other amines. These models have radj2 = 0.8448 for TA 98, and 0.8927 for TA 100. Inclusion of a third variable, Clog P, increases radj2 to 0.8913 for TA 98 and 0.9011 for TA 100. This model is significant at the 95% confidence level for all variables for TA 98, but only for two of the three variables for TA 100. The confidence level is 80% for Clog P in TA 100. Quantitative carcinogenicity data in mice and rats are more weakly correlated with log S (radj2 = 0.5357 for 12 amines in mice, radj2 = 0.4216 for 10 amines in rats). Several two parameter regression models, all containing Clog P and one containing log S, adequately correlate the mouse data.