Document Detail

The formation of 9-hydroxychrysene-1,2-diol as an intermediate in the metabolic activation of chrysene.
MedLine Citation:
PMID:  3967334     Owner:  NLM     Status:  MEDLINE    
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.
R M Hodgson; A Seidel; W Bochnitschek; H R Glatt; F Oesch; P L Grover
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Carcinogenesis     Volume:  6     ISSN:  0143-3334     ISO Abbreviation:  Carcinogenesis     Publication Date:  1985 Jan 
Date Detail:
Created Date:  1985-03-20     Completed Date:  1985-03-20     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  8008055     Medline TA:  Carcinogenesis     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  135-9     Citation Subset:  IM    
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MeSH Terms
Chrysenes / metabolism*
DNA / metabolism
Microsomes, Liver / metabolism
Phenanthrenes / metabolism*
Rats, Inbred Strains
Skin / metabolism
Grant Support
Reg. No./Substance:
0/Chrysenes; 0/Phenanthrenes; 218-01-9/chrysene; 9007-49-2/DNA; 96383-86-7/9-hydroxy-1,2-dihydro-1,2-dihydroxychrysene

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