Document Detail


Differences in mutagenicity and cytotoxicity of (+)- and (-)-benzo[a]pyrene 4,5-oxide: a synergistic interaction of enantiomers.
MedLine Citation:
PMID:  388437     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
In order to study the biological effects of (+)- and (-)-benzo[a]pyrene 4,5-oxide, a synthesis of these molecules has been developed based on the resolution of (+/-)-cis-4,5-dihydroxy-4,5-dihydrobenzo[a]pyrene. The (-) enantiomer of benzo[a]pyrene 4,5-oxide was 1.5- to 5.5-fold more mutagenic than the (+) enantiomer in strains TA 98, TA 100, TA 1537, and TA 1538 of Salmonella typhimurium and in Chinese hamster V79 cells. In studies with V79 Cells, the (-) enantiomer of benzo[a]pyrene 4,5-oxide was also more cytotoxic than the (+) enantiomer. When mixtures of the enantiomers were studied in V79 cells, synergistic cytotoxic and mutagenic responses were observed. The greatest cytotoxic and mutagenic effects occurred with a 3:1 mixture of the (-) and (+) enantiomers of benzo[a]pyrene 4,5-oxide, respectively.
Authors:
R L Chang; A W Wood; W Levin; H D Mah; D R Thakker; D M Jerina; A H Conney
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Proceedings of the National Academy of Sciences of the United States of America     Volume:  76     ISSN:  0027-8424     ISO Abbreviation:  Proc. Natl. Acad. Sci. U.S.A.     Publication Date:  1979 Sep 
Date Detail:
Created Date:  1980-01-24     Completed Date:  1980-01-24     Revised Date:  2009-11-18    
Medline Journal Info:
Nlm Unique ID:  7505876     Medline TA:  Proc Natl Acad Sci U S A     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  4280-4     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Animals
Benzopyrenes / pharmacology*
Cell Line
Cricetinae
Cytotoxins*
Drug Synergism
Epoxy Compounds
Isomerism
Mutagens*
Salmonella typhimurium / drug effects
Structure-Activity Relationship
Chemical
Reg. No./Substance:
0/Benzopyrenes; 0/Cytotoxins; 0/Epoxy Compounds; 0/Mutagens
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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