Synthesis and mutagenicity of 5-alkyl-substituted chrysene-1,2-diol-3,4-epoxides

Shantu Amin, Keith Huie, George Balanikas, Stephen S. Hecht

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

In order to explore the relationship between structure and mutagenicity of bay region diol-epoxides of chrysene substituted with an alkyl group in the bay region, we compared the mutagenicity in Salmonella typhimurium TA 100of anti-1,2-dihydroxy-3,4-epoxy-1,2,3,4-tetrahydrochrysene with its 5-methyl, 5-ethyl and 5-propyl derivatives. The results showed that anti-l,2-dihydroxy-3,4-epoxy-l,2,3,4-tetrahydro-5-methylchrysene (7400 revertants/nmol) was the most mutagenic of these diol-epoxides followed by anti-1,2-dihydroxy-3,4-epoxy-1,2,3,4-tetrahydrochrysene and its 5-ethyl derivative (1100 revertants/nmol). The 5-propyl substituted diol-epoxide was inactive at the doses tested. The results demonstrate that steric factors are dominant in the expression of methylchrysene diol-epoxide mutagenicity in S.typhimurium and suggest that the molecular shape of the 5-methyl substituted diol-epoxide leads to a unique reaction with DNA associated with high mutagenicity and tumorigenicity.

Original languageEnglish (US)
Pages (from-to)2305-2308
Number of pages4
JournalCarcinogenesis
Volume9
Issue number12
DOIs
StatePublished - Dec 1 1988

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Epoxy Compounds
Salmonella typhimurium
chrysene-1,2-diol
DNA
3,4-epoxy-1,2,3,4-tetrahydrochrysene

All Science Journal Classification (ASJC) codes

  • Cancer Research

Cite this

Amin, Shantu ; Huie, Keith ; Balanikas, George ; Hecht, Stephen S. / Synthesis and mutagenicity of 5-alkyl-substituted chrysene-1,2-diol-3,4-epoxides. In: Carcinogenesis. 1988 ; Vol. 9, No. 12. pp. 2305-2308.
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Synthesis and mutagenicity of 5-alkyl-substituted chrysene-1,2-diol-3,4-epoxides. / Amin, Shantu; Huie, Keith; Balanikas, George; Hecht, Stephen S.

In: Carcinogenesis, Vol. 9, No. 12, 01.12.1988, p. 2305-2308.

Research output: Contribution to journalArticle

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AU - Amin, Shantu

AU - Huie, Keith

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AU - Hecht, Stephen S.

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AB - In order to explore the relationship between structure and mutagenicity of bay region diol-epoxides of chrysene substituted with an alkyl group in the bay region, we compared the mutagenicity in Salmonella typhimurium TA 100of anti-1,2-dihydroxy-3,4-epoxy-1,2,3,4-tetrahydrochrysene with its 5-methyl, 5-ethyl and 5-propyl derivatives. The results showed that anti-l,2-dihydroxy-3,4-epoxy-l,2,3,4-tetrahydro-5-methylchrysene (7400 revertants/nmol) was the most mutagenic of these diol-epoxides followed by anti-1,2-dihydroxy-3,4-epoxy-1,2,3,4-tetrahydrochrysene and its 5-ethyl derivative (1100 revertants/nmol). The 5-propyl substituted diol-epoxide was inactive at the doses tested. The results demonstrate that steric factors are dominant in the expression of methylchrysene diol-epoxide mutagenicity in S.typhimurium and suggest that the molecular shape of the 5-methyl substituted diol-epoxide leads to a unique reaction with DNA associated with high mutagenicity and tumorigenicity.

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