Formation of DNA adducts in mouse skin treated with metabolites of chrysene.
Analysis by 32P-postlabelling of DNA isolated from mouse skin that had been treated in vivo with the polycyclic hydrocarbon chrysene revealed the presence of 7 adducts. All 7 adducts were also present in DNA from mice treated with trans-1,2-dihydro-1,2-dihydroxychrysene (chrysene-1,2-diol), and one of them, adduct 2, was formed from the triol derivative 9-hydroxy-trans-1,2- dihydro-1,2-dihydroxychrysene (9-hydroxychrysene-1,2-diol) and from 3-hydroxychrysene. Adducts were not detected in DNA from mice treated with trans-3,4-dihydro-3,4-dihydroxychrysene (chrysine-3,4-diol) or with 1-, 2-, 4-, 5- or 6-hydroxychrysene. In vitro modification of DNA by the anti-isomer of the bay-region diol-epoxide yielded adducts 3-7, while the corresponding triol-epoxide yielded adducts 2. It is concluded that chrysene activation in mouse skin proceeds principally via the bay-region diol-epoxide and to a lesser extent via the related bay-region triol-epoxide.
D000818:Animals; D002855:Chromatography, Thin Layer; D002911:Chrysenes / Q000494:pharmacology*; D004247:DNA / Q000378:metabolism*; D008297:Male; D051379:Mice; D010616:Phenanthrenes / Q000494:pharmacology*; D012867:Skin / Q000187:drug effects*
D002911:Chrysenes; D010616:Phenanthrenes; C031180:chrysene; C016307:chrysene-1,2-dihydrodiol; D004247:DNA