Stereoselective metabolism of benzo[c]phenanthrene to the procarcinogenic trans-3,4-dihydrodiol.
The enantiomeric compositions of benzo[c]phenanthrene trans-3,4-dihydrodiol, a metabolic precursor of the ultimate carcinogenic bay-region 3,4-dihydrodiol-1,2-epoxides, formed in the metabolism of BcPh by liver microsomes from untreated, phenobarbital (PB)-treated, 3-methylcholanthrene (MC)-treated and polychlorinated biphenyls (PCB; Aroclor 1254)-treated rats of the Sprague-Dawley and Long-Evans strain were each determined by chiral stationary-phase h.p.l.c. and circular dichroism spectral analyses. The percentage of 3R,4R enantiomer in the trans-3,4-dihydrodiol metabolite of BcPh varies, depending on the concentration of liver microsomal enzymes used and the time of incubation: 29-30% (control), 46-54% (PB), 94-100% (MC) and 90-99% (PCB).
D000818:Animals; D002273:Carcinogens / Q000378:metabolism*; D002942:Circular Dichroism; D003577:Cytochrome P-450 Enzyme System / Q000032:analysis; D007527:Isoenzymes / Q000032:analysis; D008297:Male; D008748:Methylcholanthrene / Q000494:pharmacology; D008862:Microsomes, Liver / Q000378:metabolism; D009153:Mutagens / Q000378:metabolism*; D010616:Phenanthrenes / Q000378:metabolism*; D010634:Phenobarbital / Q000494:pharmacology; D011078:Polychlorinated Biphenyls / Q000494:pharmacology; D051381:Rats; D011919:Rats, Inbred Strains; D013237:Stereoisomerism
D002273:Carcinogens; D007527:Isoenzymes; D009153:Mutagens; D010616:Phenanthrenes; D008748:Methylcholanthrene; C026153:benzo(c)phenanthrene 3,4-dihydrodiol; D003577:Cytochrome P-450 Enzyme System; D011078:Polychlorinated Biphenyls; C002615:benzo(c)phenanthrene; D010634:Phenobarbital