Comparison of the skin tumor-initiating activities of dihydrodiols, diol-epoxides, and methylated derivatives of various polycyclic aromatic hydrocarbons

Conference · Mon Jan 01 04:00:00 EST 1979

OSTI ID:5287654

Slaga, T. J.; Iyer, R. P.; Lyga, W.; Secrist, A. III; Daub, G. H.; Harvey, R. G.

The abilities of dihydrodiols and diol-epoxides of dibenz(a,h)-anthracene (DB(a,h)A), dibenz(a,c)anthracene (DB(a,c)A), chrysene, 7-methylbenz(a)anthracene (7-MB(a)A), benzo(e)pyrene (B(e)P), and various methylated derivatives of benzo(a)pyrene (B(a)P), benz(a)anthracene (B(a)A), and 3-methylcholanthrene (3-MC) to initiate skin tumors in mice were determined. The trans-3,4-dihydrodiol of 7-MB(a)A, trans 9,10-dihydrodiol of B(e)P, and trans 1,2-dihydrodiol of chrysene were more active than their corresponding parent hydrocarbon when applied topically. The trans 3,4-dihydrodiol of DB(a,h)A had one-half of the tumor-initiating ability of DB(a,h)A. The trans 3,4-dihydrodiol of chrysene and trans 10-11-dihydrodiol of DB(a,c)A were inactive as skin tumor initiators. B(e)P-9,10-diol-11,12-epoxide, DB(a,h)A 3,4-diol-1,2-epoxide, DB(a,c)A 10,11-diol-12,13-epoxide, and 7-MB(a)A, 3,4-diol-1,2-epoxide were also inactive as tumor initiators. Chrysene 1,2-diol-3,4-epoxide had 25% of the activity of chrysene. Results show that the dihydrodiols of 7-MB(a)A, DB(a,h)A, and chrysene have moderate to high initiating activity, whereas the dihydrodiol B(e)P was inactive. The bay region diol-epoxide of chrysene was the only diol-epoxide tested that had significant activity compared to the parent hydrocarbon. Substitution of a methyl group in 7-MB(a)A, 12-MB(a)A, DMB(a)A, 3-MC, and B(a)P blocked the skin tumor-initiating activity. Likewise, substitution of a methyl group in the bay region of B(a)P and DMB(a)A decreased their tumor-initiating activity. (ERB)

• Research Organization: Oak Ridge National Lab., TN (USA); Ohio State Univ., Columbus (USA). Dept. of Chemistry; New Mexico Univ., Albuquerque (USA). Dept. of Chemistry; Chicago Univ., IL (USA). Ben May Lab. for Cancer Research
• Sponsoring Organization: USDOE Office of Health and Environmental Research
• DOE Contract Number: W-7405-ENG-26
• OSTI ID: 5287654
• Report Number(s): CONF-791059--5
• Country of Publication: United States
• Language: English

Related Subjects

3-METHYLCHOLANTHRENE
550200 -- Biochemistry
550900 -- Pathology
560305* -- Chemicals Metabolism & Toxicology-- Vertebrates-- (-1987)
59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ANIMALS
AROMATICS
BENZANTHRACENE
BENZOPYRENE
BODY
CARCINOGENESIS
CHEMICAL REACTIONS
CHRYSENE
COMPARATIVE EVALUATIONS
CONDENSED AROMATICS
DATA
DATA FORMS
EPOXIDES
EXPERIMENTAL DATA
HYDROCARBONS
INFORMATION
ISOLATED VALUES
MAMMALS
METHYLATION
MICE
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
ORGANS
PATHOGENESIS
POLYCYCLIC AROMATIC HYDROCARBONS
RODENTS
SKIN
VERTEBRATES