Formation of radical cations in a model for the metabolism of aromatic hydrocarbons.
To test the hypothesis that electrophilic radical cations are the major ultimate electrophilic and carcinogenic forms of benz[a]anthracene (BA), dibenz[a,h]anthracene (DBA), and benzo[a]pyrene (BP), we have focused on a chemical model of metabolism which parallels and duplicates known or potential metabolites of some polycyclic hydrocarbons formed in cells. Studies of this model system show that radical cations are hardly formed, if at all, in the case of BA or DBA but are definitely formed in the cases of the carcinogen BP as well as the non-carcinogenic hydrocarbons, pyrene and perylene. We conclude that the carcinogenicities of BA, DBA, BP, pyrene, and perylene are independent of one-electron oxidation to radical cation intermediates.
Lehner
Andreas F
AF
Experimental Cancer Research Laboratory, Department of Veterinary Science, University of Kentucky, Lexington, KY 40536, USA.
Horn
Jamie
J
Flesher
James W
JW
D001711:Biotransformation; D002273:Carcinogens / Q000493:pharmacokinetics / Q000633:toxicity; D002412:Cations / Q000378:metabolism*; D004579:Electron Transport; D004583:Electrons; D005609:Free Radicals; D006841:Hydrocarbons, Aromatic / Q000737:chemistry* / Q000378:metabolism* / Q000493:pharmacokinetics; D010084:Oxidation-Reduction; D013329:Structure-Activity Relationship
D002273:Carcinogens; D002412:Cations; D005609:Free Radicals; D006841:Hydrocarbons, Aromatic