The formation of 9-hydroxychrysene-1,2-diol as an intermediate in the metabolic activation of chrysene.
9-Hydroxy-trans-1,2-dihydro-1,2-dihydroxychrysene (9-hydroxychrysene-1,2-diol), which may be the triol involved in the formation of a chrysene triol-epoxide-DNA adduct in mouse skin, was not detected when chrysene was incubated with rat-liver microsomal preparations. In separate experiments an excess of synthetic 9-hydroxychrysene-1,2-diol was added during the incubation of 3H-labelled chrysene with rat-liver microsomes and was then re-isolated. The triol was found to contain a radioactive product that had chromatographic properties identical to those of 9-hydroxychrysene-1,2-diol when examined by reverse-phase h.p.l.c., both before and after acetylation, by normal-phase h.p.l.c. and by t.l.c. both before and after oxidation. When treated with m-chloroperoxybenzoic acid, the synthetic 9-hydroxychrysene-1,2-diol formed products that possessed alkylating activity and that reacted with DNA in vitro. Examination of the triol-epoxides produced by oxidation of a mixture of synthetic and metabolic 9-hydroxychrysene-1,2-diol by t.l.c. suggested that the anti-isomer was formed.
D000818:Animals; D001711:Biotransformation; D002911:Chrysenes / Q000378:metabolism*; D004247:DNA / Q000378:metabolism; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism; D010616:Phenanthrenes / Q000378:metabolism*; D051381:Rats; D011919:Rats, Inbred Strains; D012867:Skin / Q000378:metabolism
D002911:Chrysenes; D010616:Phenanthrenes; C031180:chrysene; D004247:DNA; C044518:9-hydroxy-1,2-dihydro-1,2-dihydroxychrysene