Chemical rearrangement of phenol-epoxide metabolites of polycyclic aromatic hydrocarbons to quinone-methides.
Evidence of the involvement of triol-epoxide and phenol-epoxide metabolites in the metabolic activation of polycyclic hydrocarbons is accumulating. It is proposed that the phenolic OH-groups present in such epoxides will activate the epoxide moieties and permit their rearrangement to quinone-methides. These quinone-methides are highly reactive, potentially-isolable chemical entities with strong alkylating activity. In one resonance form they are resonance-stabilized carbonium ions. Only epoxides that also possess phenolic OH-groups in certain positions will form quinone-methides: these appear to include 9-hydroxybenzo [a] pyrene 4,5-oxide and the triol-epoxides 9-hydroxy-trans-1,2-dihydro-1,2-dihydroxychrysene 3,4-oxide and 2-hydroxy-trans-9,10-dihydro-9,10-dihydroxybenzo[a]pyrene 7,8-oxide.
D000818:Animals; D001711:Biotransformation; D055598:Chemical Phenomena; D002621:Chemistry; D004852:Epoxy Compounds / Q000378:metabolism*; D004988:Ethers, Cyclic / Q000378:metabolism*; D010636:Phenols / Q000378:metabolism*; D011083:Polycyclic Compounds / Q000378:metabolism*; D011809:Quinones / Q000378:metabolism; D013329:Structure-Activity Relationship
D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D010636:Phenols; D011083:Polycyclic Compounds; D011809:Quinones