Biological and Pharmaceutical Bulletin p. 541 - 546 (1996)
Update date:2022-08-31
Topics:
Saeki, Ken-Ichi
Takahashi, Kazuhiko
Kawazoe, Yutaka
4-Methylquinoline (4-MeQ) showed an extraordinarily potent mutagenicity when compared to quinolone and isomeric methylquinolines. The major metabolite of 4-MeQ was 4- hydroxymethylquinoline, which was not mutagenic under the assay condition employed. Deuteration of the methyl group of 4-MeQ resulted in a decrease in the amount of the hydroxymethyl metabolic and an increase in mutagenicity, indicating that hydroxylation of the substituent methyl group is a detoxication process. A 3-chloro derivative of 4-MeQ was proven to be non-mutagenic. 4-Ethyl- quinoline, as well as 4-hydroxymethylquinoline, was much less mutagenic than 4-MeQ. Taking account of the structure-mutagenicity relationship, a possible mechanism is proposed for the potent mutagenic potential of 4-MeQ.
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