Document Detail

Identification of 4-oxo-2-hexenal and other direct mutagens formed in model lipid peroxidation reactions as dGuo adducts.
MedLine Citation:
PMID:  16411666     Owner:  NLM     Status:  MEDLINE    
We searched for mutagens that react with 2'-deoxyguanosine (dGuo) in model systems of lipid peroxidation. To autoxidation systems of methyl linoleate (model of omega-6 fat), methyl alpha-linolenate (MLN) (model of omega-3 fat), and commercial salad oil, dGuo was added. The reaction mixtures were analyzed by HPLC. Six adducts were detected, and their structures were determined by 1H and 13C NMR, UV, and mass spectra and by comparison with synthetic authentic samples. The mutagens that reacted with dGuo to form these adducts were proposed as glyoxal, glyoxylic acid, ethylglyoxal, and 4-oxo-2-hexenal (4-OHE). The formation of 8-hydroxy-dGuo, an oxidized product of dGuo, was also detected in the model reaction mixtures. Among them, glyoxal and glyoxylic acid are known mutagens, while ethylglyoxal and 4-OHE, produced from MLN, have not been reported as mutagens thus far. We confirmed the mutagenic activity of 4-OHE with Salmonella strains, TA100 and TA104, without S9 mix. These compounds may be involved in lipid peroxide-related cancers.
Muneyuki Maekawa; Kazuaki Kawai; Yoshikazu Takahashi; Hikaru Nakamura; Takumi Watanabe; Ryuichi Sawa; Kenji Hachisuka; Hiroshi Kasai
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Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Chemical research in toxicology     Volume:  19     ISSN:  0893-228X     ISO Abbreviation:  Chem. Res. Toxicol.     Publication Date:  2006 Jan 
Date Detail:
Created Date:  2006-01-17     Completed Date:  2006-04-06     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8807448     Medline TA:  Chem Res Toxicol     Country:  United States    
Other Details:
Languages:  eng     Pagination:  130-8     Citation Subset:  IM    
Department of Environmental Oncology, Institute of Industrial Ecological Sciences, University of Occupational and Environmental Health (UOEH), 1-1, Iseigaoka, Yahatanishi-ku, Kitakyushu 807-8555, Japan.
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MeSH Terms
Aldehydes / analysis,  chemistry*,  toxicity
Deoxyguanosine / analysis,  chemistry*
Glyoxylates / analysis,  chemistry
Linoleic Acids
Linolenic Acids
Lipid Peroxidation*
Models, Biological
Mutagenicity Tests
Mutagens / analysis,  chemistry*,  toxicity
Plant Oils
Pyruvaldehyde / analogs & derivatives,  analysis,  chemistry
Salmonella / drug effects,  genetics
Reg. No./Substance:
0/4-oxo-(E)-2-hexenal; 0/Aldehydes; 0/Glyoxylates; 0/Linoleic Acids; 0/Linolenic Acids; 0/Mutagens; 0/Plant Oils; 112-63-0/methyl linoleate; 16009-13-5/Hemin; 298-12-4/glyoxylic acid; 4417-81-6/ethylglyoxal; 7361-80-0/methyl linolenate; 78-98-8/Pyruvaldehyde; 961-07-9/Deoxyguanosine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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