Carcinogenic carbocyclic and heterocyclic aromatic amines: a DFT study concerning their mutagenic potency.

BOROSKY, GABRIELA L.

Journal of Molecular Graphics and Modelling

Elsevier

Año: 2008 vol. 27 p. 459 - 465

1093-3263

The relative stability of the nitrenium ions derived from a set of 43 aromatic and heteroaromatic amines of diverse structure was evaluated by density functional theory (DFT) calculations in order to examine the role of these electrophilic intermediates on mutagenic activity. Correlations were sought between calculated properties and mutagenic potencies from the literature. Mutagenicity was found to increase with nitrenium ion stability, which was favored by negative charge development at the exocyclic nitrogen of the ion (qN). Distinct correlation functions were observed for the amines grouped according to their classification as aromatic (Ar), heteroaromatic (HAr), imidazocarbocyclic (ImiAr), imidazoheterocyclic (ImiH), dipyridoimidazoles (PI), and quinoxalines (Qx). The influence of the logarithm of the octanol/water partition coefficient (LogP) on the mutagenic potency of the amines selected for this study was also analyzed.