Benzo[e]pyrene metabolism in rat liver microsomes: dependence of the metabolite profile on the pretreatment of rats with various monooxygenase inducers.
Benzo[r]pyrene (B[e]P) is metabolized by liver microsomes of untreated rats to trans-4,5-dihydroxy-4,5-dihydrobenzo(e)pyrene and 1- as well as 3-hydroxybenzo[e]pyrene as shown by g.l.c. and mass spectrometry of their trimethylsilyl ethers. After pretreatment of the rats with various monooxygenase inducers oxidation at the 9/10-position was also observed. In addition, secondary oxidation to dihydrodiolepoxides and the formation of a tetrol, tentatively identified as 4,5,9,10-tetrahydroxy-4,5,9,10-tetrahydrobenzo[e]pyrene was detected after incubation of B[e]P with liver microsomes of rats treated with polycyclic aromatic hydrocarbons. However, no formation of the supposed ultimate carcinogen, the 9,10-dihydroxy-11,12-epoxy-9,10,11,12-tetrahydrobenzo[e]pyrene could be observed after any of the pretreatments.
D000818:Animals; D001580:Benzopyrenes / Q000378:metabolism*; D002273:Carcinogens / Q000494:pharmacology*; D002849:Chromatography, Gas; D007700:Kinetics; D008297:Male; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism*; D010634:Phenobarbital / Q000494:pharmacology; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship
D001580:Benzopyrenes; D002273:Carcinogens; C026487:benzo(e)pyrene; D010634:Phenobarbital