Document Detail

Characterization of aminoalkylimidazol-4-one mutagens from liquid-reflux models.
MedLine Citation:
PMID:  2492078     Owner:  NLM     Status:  MEDLINE    
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 mutagen formation, and elucidating the mechanism of such inhibition.
R C Jones; J H Weisburger
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Mutation research     Volume:  222     ISSN:  0027-5107     ISO Abbreviation:  Mutat. Res.     Publication Date:  1989 Jan 
Date Detail:
Created Date:  1989-02-16     Completed Date:  1989-02-16     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0400763     Medline TA:  Mutat Res     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  43-51     Citation Subset:  IM    
American Health Foundation, Naylor Dana Institute for Disease Prevention, Valhalla, NY 10595-1599.
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MeSH Terms
Chemical Phenomena
Imidazoles* / isolation & purification,  pharmacology
Mutagenicity Tests
Mutagens* / pharmacology
Salmonella typhimurium / drug effects
Grant Support
Reg. No./Substance:
0/Imidazoles; 0/Mutagens; 119290-23-2/2-amino-1-methyl-5-propylideneimidazol-4-one; 119290-24-3/2-amino-5-ethylidene-1-methylimidazol-4-one; 60-27-5/Creatinine; 72-19-5/Threonine

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