Differences in mutagenicity and cytotoxicity of (+)- and (-)-benzo(a)pyrene 4,5-oxide: a synergistic interaction of enantiomers

Journal Article · Sat Sep 01 04:00:00 EDT 1979 · Proc. Natl. Acad. Sci. U.S.A.; (United States)

DOI:https://doi.org/10.1073/pnas.76.9.4280· OSTI ID:5365613

Chang, R L ^[1]; Wood, A W; Levin, W; Mah, H D; Thakker, D R; Jerina, D M; Conney, A H

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1. Hoffmann-La Roche Inc., Nutley, NJ

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.

• OSTI ID: 5365613
• Journal Information: Proc. Natl. Acad. Sci. U.S.A.; (United States), Journal Name: Proc. Natl. Acad. Sci. U.S.A.; (United States) Vol. 76:9; ISSN PNASA
• Country of Publication: United States
• Language: English

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63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ANIMALS
AROMATICS
BACTERIA
BENZOPYRENE
BIOLOGICAL EFFECTS
CELL CULTURES
CONDENSED AROMATICS
ENANTIOMORPHS
HAMSTERS
HYDROCARBONS
MAMMALS
MICROORGANISMS
MUTAGEN SCREENING
MUTAGENESIS
ORGANIC COMPOUNDS
RODENTS
SALMONELLA
SALMONELLA TYPHIMURIUM
SCREENING
STEREOCHEMISTRY
SYNERGISM
TOLERANCE
TOXICITY
VERTEBRATES