The C2-alkylated acrolein derivatives 2-methylacrolein, 2-ethylacrolein and 2-propylacrolein are mutagenic in Salmonella typhimurium TA100. They are direct mutagens, their mutagenic potency being inversely proportional to the size of the alkylating substituent in the C2 position. In the presence of S9 mix, the mutagenicity of all these substances is considerably reduced; the reduction in mutagenicity is inversely proportional to the direct mutagenic potential of the substance. As shown for 2-methylacrolein, the reduction in mutagenicity is dependent on the concentration of S9 in the S9 mix and is not significantly influenced by heat inactivation of the S9 mix or by addition of TCPO, an inhibitor of epoxide hydrolase, to the testing system. There are no indications of enzymatic activation by the metabolizing microsomal system.
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http://dx.doi.org/10.1016/0165-7992(91)90077-h | DOI Listing |
Mutat Res
April 2002
Department of Toxicology, University of Würzburg, Versbacher Strasse 9, 97078, Germany.
alpha,beta-Unsaturated aldehydes are ubiquitous environmental pollutants, important industrial chemicals, have mani-fold biological functions in plants and insects and are natural products in food. They are endogenously formed in animals and humans during lipid peroxidation and arachidonic acid oxidation and are genotoxic, mutagenic and carcinogenic. Crotonaldehyde and 2-hexenal in food may contribute to general carcinogenicity in humans.
View Article and Find Full Text PDFEnviron Mol Mutagen
August 2001
Department of Toxicology, University of Würzburg, Würzburg, Germany.
alpha,beta-Unsaturated aldehydes are a class of mutagenic and carcinogenic compounds that form promutagenic 1,N(2)-propanodeoxyguanosine adducts. They are important industrial and environmental compounds, are formed endogenously, and are found in food. We recently published structure-mutagenicity relationships for 3-alkyl substituted alpha,beta-unsaturated aldehydes (beta-alkylacroleins) and here we present structural influences on the mutagenicity of the 2-alkyl substituted alpha,beta-unsaturated aldehydes (alpha-alkylacroleins), 2-methylacrolein, 2-ethylacrolein, 2-propylacrolein, and 2-butylacrolein, in Salmonella typhimurium TA 100.
View Article and Find Full Text PDFMutat Res
December 1991
Institute of Toxicology, University of Würzburg, Germany.
The C2-alkylated acrolein derivatives 2-methylacrolein, 2-ethylacrolein and 2-propylacrolein are mutagenic in Salmonella typhimurium TA100. They are direct mutagens, their mutagenic potency being inversely proportional to the size of the alkylating substituent in the C2 position. In the presence of S9 mix, the mutagenicity of all these substances is considerably reduced; the reduction in mutagenicity is inversely proportional to the direct mutagenic potential of the substance.
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