Prediction of the genotoxicity of aromatic and heteroaromatic amines using electrotopological state indices

In the past decade, electrotopological state (E-state) indices have come into their own as useful descriptors for correlating a variety of physicochemical and biological properties of chemical compounds. Genotoxicity and mutagenicity, however, appear not to have been previously considered. In the present study, the genotoxicity of a set of 95 aromatic and heteroaromatic amines, which has been modeled previously using several sets of parameters, is modeled using E-state indices, both with and without principal components analysis. Parallels are drawn between E-state indices that were important in these models and other types of descriptors found significant in previous studies, thus, shedding light on connections to the molecular mechanism of activity. The best result had a correlation coefficient r = 0.876 and a standard error s less than or equal to 1 log unit. These values are comparable to those in previously published models that were based on topological/geometric or on physicochemical parameters. They are not as good as those for a model based on descriptors derived from extensive quantum mechanical analysis, but E-state indices are much easier to compute. Published by Elsevier Science B.V.