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Possible role of 6‐hydroxymethylbenzo[a]pyrene as a proximate carcinogen of benzo[a]pyrene and 6‐methylbenzo[a]pyrene
Author(s) -
Flesher James W.,
Sydnor Katherine L.
Publication year - 1973
Publication title -
international journal of cancer
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.475
H-Index - 234
eISSN - 1097-0215
pISSN - 0020-7136
DOI - 10.1002/ijc.2910110221
Subject(s) - pyrene , carcinogen , benzo(a)pyrene , chemistry , methylation , benzopyrene , metabolism , biochemistry , stereochemistry , organic chemistry , dna
Benzo[a]pyrene (B[a]P) and 6‐methylbenzo[a]pyrene ( 6‐MeB[a]P) are metabolized by fortified rat‐liver homogenates to a number of metabolites including one which is indistinguishable from 6‐hydroxymethylbenzo[a]pyrene (6–OHMeB[a]P) by either thin‐layer chromatography or ultra‐violet absorption spectra. This compound is a potent carcinogen when administered by subcutaneous injection to rats. These observations are in accord with the hypothesis that methylation or hydroxymethylation is one of the first steps in metabolic activation of carcinogenic polycyclic hydrocarbons.