One-Electron Oxidation of Dibenzopyrenes by Manganic Acetate

Article abstract of DOI:10.1021/jo00038a015

The dibenzopyrenes (DBPs) are carcinogenic polycyclic aromatic hydrocarbons (PAH) found as environmental pollutants.DBP is the most potent carcinogenic PAH ever tested.To investigate the bioactivation of DBPs by one-electron oxidation, oxidation of DBP, DBP, DBP, DBP, and anthanthrene with Mn(OAc)3 was conducted and compared to that of benzopyrene (BP).All five DBPs produced monoacetoxy derivatives, and all of them except DBP also produced diacetoxy derivatives.Kinetic studies of the formation of monoacetoxy and diacetoxy derivatives of DBPs were carried out and the results were compared to those of the parent compound BP.DBP was similar to BP.DBP reacted inefficiently to form monoacetoxy and diacetoxy products.The other three DBPs resembled one another.These results provide preliminary essential information for studies of the bioactivation of the very potent carcinogen DBP to form DNA adducts.