Document Detail

Carcinogenicity of benzo-ring derivatives of benzo(a)pyrene on mouse skin.
MedLine Citation:
PMID:  884679     Owner:  NLM     Status:  MEDLINE    
Benzo(a)pyrene (BP) and several benzo-ring derivatives of BP were tested for carcinogenic activity in mice by topical application of each compound once every 2 weeks for 60 weeks. Chronic treatment of C57BL/6J mice with (+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene (0.025 to 0.10 micronmole/application) indicated that the dihydrodiol was slightly more active as a complete carcinogen than the parent hydrocarbon BP. 7,8-Dihydroxy-7,8,9,10-tetrahydro-benzo(a)pyrene, a compound related to (+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene but which lacks the double bond at position 9,10, was inactive as a carcinogen on mouse skin. These results indicate the importance of the double bond at position 9,10 for the carcinogenic activity of (+/-)-trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene. Chronic treatment of mice with -.4 micronmole of the highly mutagenic (+/-)-7,beta,8alpha-dihydroxy-9alpha, 10alpha-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene, (+/-)-7beta,8alpha-dihydroxy-9beta, 10beta-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene, or 9,10-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene every 2 weeks for 60 weeks resulted in tumor incidences of 0, 8, and 4%, respectively, whereas BP at this dose caused a 100% tumor incidence. The high reactivity of the three epoxides may account for their inactivity or their weak carcinogenic activity on mouse skin.
W Levin; A W Wood; P G Wislocki; J Kapitulnik; H Yagi; D M Jerina; A H Conney
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Cancer research     Volume:  37     ISSN:  0008-5472     ISO Abbreviation:  Cancer Res.     Publication Date:  1977 Sep 
Date Detail:
Created Date:  1977-09-29     Completed Date:  1977-09-29     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  2984705R     Medline TA:  Cancer Res     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  3356-61     Citation Subset:  IM    
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MeSH Terms
Animals, Newborn
Benzopyrenes / administration & dosage,  toxicity*
Chemical Phenomena
Drug Administration Schedule
Epoxy Compounds / toxicity
Glycols / toxicity
Mice, Inbred C57BL
Neoplasms, Experimental / chemically induced
Skin Neoplasms / chemically induced*
Structure-Activity Relationship
Reg. No./Substance:
0/Benzopyrenes; 0/Carcinogens; 0/Epoxy Compounds; 0/Glycols

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