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
 

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 · · Cancer Res.; (United States)
OSTI ID:6941334
 [1]; ; ; ; ; ;
  1. Oak Ridge National Lab., TN
+ Show Author Affiliations

The abilities of the optically pure (+)- and (-)-enantiomers of the diastereomeric 7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrenes derived from the enantiomeric trans-7,8-dihydrodiols to initiate skin tumors in mice were determined with a two-stage system of tumorigenesis. As a tumor initiator, (+)-7,..beta..,8..cap alpha..-dihydroxy-9..cap alpha..,10..cap alpha..-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene 2 was approximately 60% as active as was benzo(a)pyrene, whereas (-)-7..cap alpha..,8..beta..-dihydroxy-9..beta..,10..beta..-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene 2 was about 2% as active as was benzo(a)pyrene. The tumor-initiating ability of (+)-7,..beta..,8..cap alpha..-dihydroxy-9..cap alpha..,10..cap alpha..-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene 2 was found to be greater when given daily for 6 days at a dose of 34 nmol/day than when given once at a 200-nmol dose level. Similar fractionated doses of benzo(a)pyrene or (-)-7..cap alpha..,8..beta..-dihydroxy-9..beta..-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene 2 did not increase their skin tumor-initiating activity. The data suggest that (+)-7..beta..,8..cap alpha..-dihydroxy-9..cap alpha..,10..cap alpha..-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene is an ultimate carcinogenic form of benzo(a)pyrene.

DOE Contract Number:
W-7405-ENG-26
OSTI ID:
6941334
Journal Information:
Cancer Res.; (United States), Journal Name: Cancer Res.; (United States) Vol. 39; ISSN CNREA
Country of Publication:
United States
Language:
English

Similar Records

Differences in mutagenicity of the optical enantiomers of the diasteromeric benzo(a)pyrene 7,8-diol-9,10-epoxides
Journal Article · Mon Aug 22 00:00:00 EDT 1977 · Biochem. Biophys. Res. Commun.; (United States) · OSTI ID:5205192
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
Comparison of the tumor-initiating activities of benzo(a)pyrene arene oxides and diol-epoxides. [Mice, skin]
Journal Article · Mon Oct 31 23:00:00 EST 1977 · Cancer Res.; (United States) · OSTI ID:6751190

Related Subjects

560305* -- Chemicals Metabolism & Toxicology-- Vertebrates-- (-1987)
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ANIMALS
AROMATICS
BENZOPYRENE
BODY
CARCINOGENESIS
COMPARATIVE EVALUATIONS
CONDENSED AROMATICS
DISEASES
DOSE-RESPONSE RELATIONSHIPS
HYDROCARBONS
MAMMALS
MICE
NEOPLASMS
ORGANIC COMPOUNDS
ORGANS
PATHOGENESIS
RODENTS
SKIN
VERTEBRATES