Metabolic activation of chrysene in mouse skin: evidence for involvement of a triol-epoxide

All three possible dihydrodiols of chrysene and a chrysene triol, formed from the further metabolism of the chrysene-1,2-diol, were detected when ether extracts of mouse skin that had been treated with 3-labelled chrysene were examined by h.p.l.c. The major deoxyribonucleoside-hydrocarbon adducts pr...

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Bibliographic Details
Published in:Carcinogenesis (New York) 1983-12, Vol.4 (12), p.1639-1643
Main Authors: Hodgeson, R. M., Weston, A., Grover, P. L.
Format: Article
Language:English
Subjects:
Animals
Biological and medical sciences
Biotransformation
Carcinogenesis, carcinogens and anticarcinogens
Chemical agents
Chromatography, High Pressure Liquid
Chrysenes - metabolism
Chrysenes - pharmacology
DNA - metabolism
Male
Medical sciences
Mice
Microsomes, Liver - metabolism
Phenanthrenes - metabolism
Rats
Skin - metabolism
Tritium
Tumors
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Summary:All three possible dihydrodiols of chrysene and a chrysene triol, formed from the further metabolism of the chrysene-1,2-diol, were detected when ether extracts of mouse skin that had been treated with 3-labelled chrysene were examined by h.p.l.c. The major deoxyribonucleoside-hydrocarbon adducts present in hydrolysates of DNA isolated from the mouse skin were examined by chromatography on Sephadex LH20 and by h.p.l.c. on Zorbax ODS. One adduct had chromato-graphic properties identical to those of the major adduct formed when r-1,t-2-dihydroxy-t-3,4-oxy-1,2,3,4-tetrahydrochrysene reacts with DNA. A second major adduct was present that had chromatographic properties that were indistinguishable from those of an adduct that was formed when either chrysene-1,2-diol or 3-hydroxychrysene were incubated with DNA in a rat liver microsomal metabolising system. The results provide evidence that this new adduct is formed via the reaction of a ‘triol-epoxide’, that appears to be 9-hydroxychrysene-1,2-diol 3,4-oxide, with DNA in mouse skin.
ISSN:0143-3334
1460-2180
DOI:10.1093/carcin/4.12.1639