EFFECTS OF METHYL AND FLUORINE SUBSTITUTION ON THE METABOLIC ACTIVATION AND TUMORIGENICITY OF POLYCYCLIC AROMATIC HYDROCARBONS.

Stephen S. Hecht, Shantu Amin, Assieh A. Melikian, Edmond J. LaVoie, Dietrich Hoffmann

Research output: Chapter in Book/Report/Conference proceedingConference contribution

48 Scopus citations

Abstract

The effects of methyl and fluorine substitution on the metabolic activation and tumorigenicity of polycyclic aromatic hydrocarbons (PAH) are reviewed. The structural requirements favoring tumorigenicity of methylated PAH are a bay region methyl group and a free peri position, both adjacent to an unsubstituted angular ring. The enhancing effect of a bay region methyl group on PAH tumorigenicity appears to be due to the relatively high reactivity with DNA and exceptional tumorigenicity of a dihydrodiol epoxide metabolite having a methyl group and epoxide ring in the same bay region.

Original languageEnglish (US)
Title of host publicationACS Symposium Series
EditorsRonald G. Harvey
PublisherACS
Pages85-105
Number of pages21
ISBN (Print)0841209243
StatePublished - Dec 1 1985

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