Skip to main content
OSTI.GOVU.S. Department of Energy Office of Scientific and Technical Information
U.S. Department of Energy
Office of Scientific and Technical Information
 

Differences in mutagenicity of the optical enantiomers of the diasteromeric benzo(a)pyrene 7,8-diol-9,10-epoxides

Journal Article · · Biochem. Biophys. Res. Commun.; (United States)
 [1]; ; ; ; ; ;
  1. Hoffmann-La Roche Inc., Nutley, NJ
+ Show Author Affiliations

Substantial differences in the mutagenic activities of the optically pure (+)- and (-)-enantiomers of the diastereomeric 7,8-dihydroxy-9, 10-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrenes were observed in strains TA98 and TA100 of Salmonella typhimurium and Chinese hamster V79 cells. In strains TA98 and TA100 (-)-7..beta..,8..cap alpha..-dihydroxy-9..beta.., 10..beta..-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene was the most mutagenic compound, inducing from 1.3 to 9.5 times as many mutations as the three other optically active stereoisomers. In Chinese hamster cells (+)-7..beta..,8..cap alpha..-dihydroxy-9..cap alpha.., 10..cap alpha..-epoxy-oxy-7,8,9,10-tetrahydrobenzo(a)pyrene was the most mutagenic compound inducing from 6 to 18 times as many variant colonies as the three other isomers. These results with known metabolites of the environmental carcinogen benzo(a)pyrene represent the first report of differences in mutagenic activity among optical enantiomers.

OSTI ID:
5205192
Journal Information:
Biochem. Biophys. Res. Commun.; (United States), Journal Name: Biochem. Biophys. Res. Commun.; (United States) Vol. 77:4; ISSN BBRCA
Country of Publication:
United States
Language:
English

Similar Records

Marked differences in the skin tumor-initiating activities of the optical enantiomers of the diastereomeric benzo(a)pyrene 7,8-diol-9,10-epoxides. [Mice]
Journal Article · Sun Dec 31 23:00:00 EST 1978 · Cancer Res.; (United States) · OSTI ID:6941334
Fungal oxidation of (+-)-9,10-dihydroxy-9,10-dihydrobenzo(a)pyrene: formation of diastereomeric benzo(a)pyrene 9,10-diol 7,8-epoxides
Journal Article · Fri Aug 01 00:00:00 EDT 1980 · Proc. Natl. Acad. Sci. U.S.A.; (United States) · OSTI ID:6850410
Conformations of adducts and kinetics of binding to DNA of the optically pure enantiomers of anti-benzo(a)pyrene diol epoxide
Journal Article · Wed Jul 18 00:00:00 EDT 1984 · Biochem. Biophys. Res. Commun.; (United States) · OSTI ID:5047981

Related Subjects

560301* -- Chemicals Metabolism & Toxicology-- Cells-- (-1987)
560302 -- Chemicals Metabolism & Toxicology-- Microorganisms-- (-1987)
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ALCOHOLS
ANIMAL CELLS
ANIMALS
AROMATICS
BACTERIA
BENZOPYRENE
BIOLOGICAL EFFECTS
CONDENSED AROMATICS
ENANTIOMORPHS
EPOXIDES
GLYCOLS
HAMSTERS
HYDROCARBONS
HYDROXY COMPOUNDS
MAMMALS
METABOLISM
MICROORGANISMS
MUTAGENS
MUTATION FREQUENCY
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
RODENTS
SALMONELLA
SALMONELLA TYPHIMURIUM
VERTEBRATES