Synthesis of 6-methylchrysene-l,2-diol-3,4-epoxides and comparison of their mutagenicity to 5-methylchrysene-l,2-diol-3,4-epoxides

Shantu Amin, Keith Huie, Stephen S. Hecht, Ronald G. Harvey

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The syn- and anti-isomers of l,2-dihydroxy-3,4-epoxy-l,2,3,4-tetrahydro-6-methykhrysene (6-MeC-l,2-diol-3,4-epoxide) were synthesized and their mutagenk activities in Salmonella typhimurium were compared with those of the syn- and anti-isomers of l,2-dihydroxy-3,4-epoxy-l,2,3,4-tetrahydro-5-methykhrysene (5-MeC-l,2-diol-3,4-epoxide). The most mu-tagenic compound was anti-5-MeC-l,2-diol-3,4-epoxide, followed by syn-5-MeC-l,2-diol-3,4-epoxide. At the same doses, neither of the 6-MeC-l, 2-dioI-3, 4-poxides was mutagenic. These results demonstrate the enhancing effect on mutagenicity of a methyl group in the same bay region as the epoxide ring of a diol epoxide.

Original languageEnglish (US)
Pages (from-to)2067-2070
Number of pages4
JournalCarcinogenesis
Volume7
Issue number12
DOIs
StatePublished - Dec 1 1986

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Epoxy Compounds
Salmonella typhimurium
5-methylchrysene
6-methylchrysene

All Science Journal Classification (ASJC) codes

  • Cancer Research

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title = "Synthesis of 6-methylchrysene-l,2-diol-3,4-epoxides and comparison of their mutagenicity to 5-methylchrysene-l,2-diol-3,4-epoxides",
abstract = "The syn- and anti-isomers of l,2-dihydroxy-3,4-epoxy-l,2,3,4-tetrahydro-6-methykhrysene (6-MeC-l,2-diol-3,4-epoxide) were synthesized and their mutagenk activities in Salmonella typhimurium were compared with those of the syn- and anti-isomers of l,2-dihydroxy-3,4-epoxy-l,2,3,4-tetrahydro-5-methykhrysene (5-MeC-l,2-diol-3,4-epoxide). The most mu-tagenic compound was anti-5-MeC-l,2-diol-3,4-epoxide, followed by syn-5-MeC-l,2-diol-3,4-epoxide. At the same doses, neither of the 6-MeC-l, 2-dioI-3, 4-poxides was mutagenic. These results demonstrate the enhancing effect on mutagenicity of a methyl group in the same bay region as the epoxide ring of a diol epoxide.",
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Synthesis of 6-methylchrysene-l,2-diol-3,4-epoxides and comparison of their mutagenicity to 5-methylchrysene-l,2-diol-3,4-epoxides. / Amin, Shantu; Huie, Keith; Hecht, Stephen S.; Harvey, Ronald G.

In: Carcinogenesis, Vol. 7, No. 12, 01.12.1986, p. 2067-2070.

Research output: Contribution to journalArticle

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AB - The syn- and anti-isomers of l,2-dihydroxy-3,4-epoxy-l,2,3,4-tetrahydro-6-methykhrysene (6-MeC-l,2-diol-3,4-epoxide) were synthesized and their mutagenk activities in Salmonella typhimurium were compared with those of the syn- and anti-isomers of l,2-dihydroxy-3,4-epoxy-l,2,3,4-tetrahydro-5-methykhrysene (5-MeC-l,2-diol-3,4-epoxide). The most mu-tagenic compound was anti-5-MeC-l,2-diol-3,4-epoxide, followed by syn-5-MeC-l,2-diol-3,4-epoxide. At the same doses, neither of the 6-MeC-l, 2-dioI-3, 4-poxides was mutagenic. These results demonstrate the enhancing effect on mutagenicity of a methyl group in the same bay region as the epoxide ring of a diol epoxide.

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