Comparison of the tumor-initiating activities of benzo(a)pyrene arene oxides and diol-epoxides
- PMID: 908047
Comparison of the tumor-initiating activities of benzo(a)pyrene arene oxides and diol-epoxides
Abstract
The ability of arene oxides, and diol epoxides of benzo(a)pyrene to initiate skin tumors in mice was determined by using a two-stage system of tumorigenesis. (+/-)-7beta,8alpha-Dihydroxy-9alpha, 10alpha-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene was a more effective tumor initiator than was (+/-)-7beta,8alpha-dihydroxy-9beta,10beta-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene when applied topically to CD-1 mice and then followed by twice-weekly applications of the promotor 12-O-tetradecanoylphorbol-13-acetate. (+/-)-7beta,8alpha-Dihydroxy-9alpha,10alpha-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene was approximately 20 to 30% as active as benzo(a)pyrene was as a tumor initiator. (+/-)-7beta,8alpha-Dihydroxy-7beta,8beta-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene, benzo(a)pyrene, 9,10-oxide, and benzo(a)pyrene 11, 12-oxide, possessed about 1, 2, and 10%, respectively, of the tumor-initiating activity of benzo(a)pyrene.
Similar articles
-
Tumorigenicity of the optical enantiomers of the diastereomeric benzo[a]pyrene 7,8-diol-9,10-epoxides in newborn mice: exceptional activity of (+)-7beta,8alpha-dihydroxy-9alpha,10alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene.Proc Natl Acad Sci U S A. 1978 Nov;75(11):5358-61. doi: 10.1073/pnas.75.11.5358. Proc Natl Acad Sci U S A. 1978. PMID: 281685 Free PMC article.
-
Epidermal hyperplasia after topical application of benzo (a) pyrene, benzo (a) pyrene diol epoxides, and other metabolites.Cancer Res. 1977 Apr;37(4):984-90. Cancer Res. 1977. PMID: 844052
-
Carcinogenicity of benzo-ring derivatives of benzo(a)pyrene on mouse skin.Cancer Res. 1977 Sep;37(9):3356-61. Cancer Res. 1977. PMID: 884679
-
Tumorigenicity studies with diol-epoxides of benzo(a)pyrene which indicate that (+/-)-trans-7beta,8alpha-dihydroxy-9alpha,10alpha-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene is an ultimate carcinogen in newborn mice.Cancer Res. 1978 Feb;38(2):354-8. Cancer Res. 1978. PMID: 620406
-
Fifty years of benzo(a)pyrene.Nature. 1983 Jun 9-15;303(5917):468-72. doi: 10.1038/303468a0. Nature. 1983. PMID: 6304528 Review. No abstract available.
Cited by
-
Role of cytochrome P-450 and related enzymes in the pulmonary metabolism of xenobiotics.Environ Health Perspect. 1984 Apr;55:359-67. doi: 10.1289/ehp.8455359. Environ Health Perspect. 1984. PMID: 6376107 Free PMC article. Review.
-
The molecular etiology and prevention of estrogen-initiated cancers: Ockham's Razor: Pluralitas non est ponenda sine necessitate. Plurality should not be posited without necessity.Mol Aspects Med. 2014 Apr;36:1-55. doi: 10.1016/j.mam.2013.08.002. Epub 2013 Aug 30. Mol Aspects Med. 2014. PMID: 23994691 Free PMC article. Review.
-
Tumorigenicity of the optical enantiomers of the diastereomeric benzo[a]pyrene 7,8-diol-9,10-epoxides in newborn mice: exceptional activity of (+)-7beta,8alpha-dihydroxy-9alpha,10alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene.Proc Natl Acad Sci U S A. 1978 Nov;75(11):5358-61. doi: 10.1073/pnas.75.11.5358. Proc Natl Acad Sci U S A. 1978. PMID: 281685 Free PMC article.
-
Specificity of chemiluminescence in the metabolism of benzo[a]pyrene to its carcinogenic diol epoxide.Proc Natl Acad Sci U S A. 1981 Feb;78(2):940-2. doi: 10.1073/pnas.78.2.940. Proc Natl Acad Sci U S A. 1981. PMID: 6785756 Free PMC article.
-
Identification of four trans-3,4-dihydrodiol metabolites of 7,12-dimethylbenz[a]anthracene and their in vitro DNA-binding activities upon further metabolism.Proc Natl Acad Sci U S A. 1978 Nov;75(11):5466-70. doi: 10.1073/pnas.75.11.5466. Proc Natl Acad Sci U S A. 1978. PMID: 103094 Free PMC article.