A QSAR model of PAHs carcinogenesis based on thermodynamic stabilities of biactive sites

Polycyclic aromatic hydrocarbons (PAHs) have been adopted to study the carcinogenesis of chemicals experimentally and theoretically. A model of carcinogenic activity of 48 PAHs was obtained based on the calculated relative thermodynamic stabilities of epoxide and carbonium intermediates of the PAHs. Using both epoxyl-energy and cationized-energy of two active sites, the model reasonably predicts the carcinogenic activity of these PAHs and shows a good ability to distinguish between carcinogenic and noncarcinogenic PAHs. Furthermore, the model suggests that double active sites and their distance characteristics are important factors in the chemical carcinogenesis of PAHs. The physical meaning of the energies corresponding addition reactions with DNA is also discussed.