PMID: 2492078Jan 1, 1989Paper

Characterization of aminoalkylimidazol-4-one mutagens from liquid-reflux models

Mutation Research
R C Jones, J H Weisburger

Abstract

A new class of low molecular weight, aminomethylimidazol-4-one (IQ-"like") mutagens have been produced by the reaction of creatinine with the amino acid L-threonine, in liquid-reflux models, mimicking cooking, of diethylene glycol:5% distilled water (2 h at 150 degrees C). Two mutagens, 2-amino-1-methyl-5-propylideneimidazol-4-one (AMPI) and 2-amino-5-ethylidene-1-methylimidazol-4-one (AEMI) were isolated and characterized by UV absorption spectra, mass spectra, and 1H-NMR. The mutagen AEMI was identical to that obtained from the reaction of creatinine with acetaldehyde. These mutagens were positive in all IQ-sensitive Ames tester strains and were not inactivated by acidic nitrosation at pH 1.0. Products displaying mutagenicity were also obtained by refluxing creatinine with other hydroxyamino acids such as L-serine, L-homoserine, and L-4-amino-3-hydroxybutyric acid, and aldehydes such as glyoxal, methylglyoxal, glycolaldehyde, but not formaldehyde. Simple model systems such as creatinine and acetaldehyde may be useful in more clearly defining the exact mechanism of formation of IQ-type mutagens (aminomethylimidazo-quinolines and -quinoxalines) produced during cooking, as well as in screening for potential inhibitors of IQ-type...Continue Reading

References

Jan 1, 1985·Environmental Mutagenesis·L L Vuolo, G J Schuessler
Aug 1, 1985·Mutation Research·H HayatsuH F Mower
Jan 1, 1984·Carcinogenesis·J S FeltonF T Hatch
Aug 1, 1982·Mutation Research·L F BjeldanesJ S Felton

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Citations

Mar 1, 1991·Mutation Research·M JägerstadK Olsson
Sep 1, 1993·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·K Skog
Jul 14, 2000·Physiological Reviews·M Wyss, R Kaddurah-Daouk

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