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

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

Laboratory Medicine and Pathology

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

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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 language	English (US)
Title of host publication	ACS Symposium Series
Editors	Ronald G. Harvey
Publisher	ACS
Pages	85-105
Number of pages	21
ISBN (Print)	0841209243
State	Published - Dec 1 1985

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title = "EFFECTS OF METHYL AND FLUORINE SUBSTITUTION ON THE METABOLIC ACTIVATION AND TUMORIGENICITY OF POLYCYCLIC AROMATIC HYDROCARBONS.",

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.",

author = "Hecht, {Stephen S.} and Shantu Amin and Melikian, {Assieh A.} and LaVoie, {Edmond J.} and Dietrich Hoffmann",

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T1 - EFFECTS OF METHYL AND FLUORINE SUBSTITUTION ON THE METABOLIC ACTIVATION AND TUMORIGENICITY OF POLYCYCLIC AROMATIC HYDROCARBONS.

AU - Hecht, Stephen S.

AU - Amin, Shantu

AU - Melikian, Assieh A.

AU - LaVoie, Edmond J.

AU - Hoffmann, Dietrich

PY - 1985/12/1

Y1 - 1985/12/1

N2 - 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.

AB - 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.

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M3 - Conference contribution

AN - SCOPUS:0022267029

SN - 0841209243

SP - 85

EP - 105

BT - ACS Symposium Series

A2 - Harvey, Ronald G.

PB - ACS

ER -

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

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