Structure, function and carcinogenicity of metabolites of methylated and non-methylated polycyclic aromatic hydrocarbons: a comprehensive review

Toxicology Mechanisms and Methods
J W Flesher, Andreas F Lehner

Abstract

The Unified Theory of PAH Carcinogenicity accommodates the activities of methylated and non-methylated polycyclic aromatic hydrocarbons (PAHs) and states that substitution of methyl groups on meso-methyl substituted PAHs with hydroxy, acetoxy, chloride, bromide or sulfuric acid ester groups imparts potent cancer producing properties. It incorporates specific predictions from past researchers on the mechanism of carcinogenesis by methyl-substituted hydrocarbons, including (1) requirement for metabolism to an ArCH2X type structure where X is a good leaving group and (2) biological substitution of a meso-methyl group at the most reactive center in non-methylated hydrocarbons. The Theory incorporates strong inferences of Fieser: (1) The mechanism of carcinogenesis involves a specific metabolic substitution of a hydrocarbon at its most reactive center and (2) Metabolic elimination of a carcinogen is a detoxifying process competitive with that of carcinogenesis and occurring by a different mechanism. According to this outlook, chemical or biochemical substitution of a methyl group at the reactive meso-position of non-methylated hydrocarbons is the first step in the mechanism of carcinogenesis for most, if not all, PAHs and the most p...Continue Reading

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Citations

Aug 23, 2016·Fertility and Sterility·Erika T Chow, Shruthi Mahalingaiah
Jan 2, 2020·Genes and Environment : the Official Journal of the Japanese Environmental Mutagen Society·Pei-Hsin ChouYi-Po Yeh
Jun 3, 2017·Bundesgesundheitsblatt, Gesundheitsforschung, Gesundheitsschutz·Ulrike PabelReiner Wittkowski
Feb 21, 2021·The Science of the Total Environment·Yang ZhaoShaoyou Lu
May 11, 2018·Chemical Research in Toxicology·Alf Claesson, Alexander Minidis

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