Publication Date:
1978-02-17
Description:
The formation, stereostructure, and cellular reactions of the 7,8-diol-9,10-epoxide metabolites of the carcinogen benzo[a]pyrene have been examined after topical application of benzo[a]pyrene to the skin of mice. In this known target tissue, polymer adducts from diastereomeric diol epoxides, (+)-(7S, 8R, 9R, 10R) and (+)-(7R, 8S, 9R, 10R), were formed stereospecifically from their corresponding 7,8-dihydrodiols. Both diol epoxides bind with proteins, RNA, and DNA in vivo. For the nucleic acids, binding occurs preferentially at the 2-amino group of guanine in cellular RNA and DNA in vivo. Methods for establishing the structure of the cellular adducts as well as the possible biological implications of their formation are discussed.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Koreeda, M -- Moore, P D -- Wislocki, P G -- Levin, W -- Yagi, H -- Jerina, D M -- New York, N.Y. -- Science. 1978 Feb 17;199(4330):778-81.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/622566" target="_blank"〉PubMed〈/a〉
Keywords:
Animals
;
Benzopyrenes/*metabolism
;
Chromatography, High Pressure Liquid
;
DNA/*metabolism
;
Epoxy Compounds/metabolism
;
Female
;
Mice
;
Mice, Inbred C57BL
;
Molecular Conformation
;
Proteins/*metabolism
;
RNA/*metabolism
;
Skin/*metabolism
;
Stereoisomerism
Print ISSN:
0036-8075
Electronic ISSN:
1095-9203
Topics:
Biology
,
Chemistry and Pharmacology
,
Computer Science
,
Medicine
,
Natural Sciences in General
,
Physics
