In vitro metabolism of selected fluoro analogs of 7,12-dimethylbenz[a]anthracene

We have compared the metabolite profiles generated from the rat liver incubation of monofluorinated derivatives of 7,12-dimethylbenz[a]anthracene. These monofluoro analogs are known to exhibit varying degrees of carcinogenicity. In this study we observed that the presence of fluorine substituents blocked metabolism at the fluorinated positions, some of which may be critical for biological activity. Furthermore, we also found that the fluorine substituents affected the chemical reactivity of the 5,6-arene oxide metabolites in terms of their ability to undergo methanolysis.