ONE-ELECTRON OXIDATION OF DIBENZO[A]PYRENES BY MANGANIC ACETATE

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