Several α,β-unsaturated carbonylic compounds and their corresponding allylic alcohols were tested in a modified Salmonella typhimurium mutagenicity assay according to Rannug et al. (1976) with and without metabolic activation by S9 mix. The mutagenic activities of the test substances were correlated with their chemical structures. Allyl alcohol exerted a significant direct mutagenic activity despite its lack of a good leaving (750 revertants/μmole). Glycidol, the epoxide of allyl alcohol, showed a lower direct mutagenic potential (80 revertants/μmole), whereas the corresponding aldehyde, acrolein, exhibited a direct mutagenicity 3 times higher than that of allyl alcohol. The possibility of an oxidation of allyl alcohol to its corresponding α,β-unsaturated carbonyl compound, acrolein, by bacterial alcohol dehydrogenase is discussed. The 3 methyl-substituted homologues of allyl alcohol, crotyl alcohol, 2-methallyl alcohol and 3-buten-2-ol, only showed borderline mutagenicity, while the higher homologs, 2-cyclohexen-1-ol, cinnamyl alcohol, geraniol and linalood, did not show any mutagenic properties. In contrasst with the methyl-substituted homologs of allyl alcohol, the methylated homologs of acrolein, croton aldehyde, 2-methylacrolein and methylvinyl ketone, were clearly mutagenic. Of the higher α,β-unsaturated carbonyl compounds tested in this study, only 2-cyclohexen-1-one, which has the lowest molecular weight, exerted a very small direct mutagenic effect, whereas cinnamylaldehyde and citral did not show any mutagenicity. The addition of S9 mix invariably led to a decrease in mutagenicity; this is most distinct with those compounds that had the highest direct mutagenic potential. The chemical reactivity of acrolein with deoxyadenosine was confirmed in an experiment in vitro.

Structure-mutagenicity relationship in α,β-unsaturated carbonylic compounds and their corresponding allylic alcohols

The use of mercapturic acids (N-acetyl-L-cysteine S-conjugates, MAs) in the biological monitoring of human exposure to environmental and industrial chemicals is receiving more and more attention. Mercapturic acids (MAs) are formed from glutathione (GSH) S-conjugates via the MA-pathway. Although this pathway can lead to different end-products, the formation of MAs is the predominant route in most species, including man. Two GSH S-transferases (GSTs) show genetic polymorphisms in humans and this can have major consequences for individual susceptibility to toxic effects and for MA formation. In occupational toxicology, adducts to biomacromolecules are also used as biomarkers. DNA adducts are a measure for the effective dose, while protein adducts are related to the dose at critical site. Both type of adducts are normally determined in blood, while MAs are determined in urine. Most MAs are excreted with relatively short half-lifes, allowing a direct evaluation of the occupational circumstances. For many compounds similar (linear) dose-dependency was found for MA excretion, formation of macromolecular adducts, and for various biomarkers of toxic effects. These relations together with fact that MAs relate to the electrophilic character of compounds, allows for the conclusion that MAs are biomarkers of toxicologically relevant internal doses of chemicals or their metabolites. An overview will be given here of the use of MAs in the assessment of internal human exposure to electrophilic environmental and industrial chemicals. Additionally, the formation of GSH S-conjugates, their catabolism to MAs and several of the frequently used analytical approaches are discussed. When appropriate, the influence of genetic polymorphisms on formation of MAs and on susceptibility to toxicity will be discussed for different chemicals as well.

Mercapturic acids as biomarkers of exposure to electrophilic chemicals: applications to environmental and industrial chemicals.

High-performance liquid chromatographic-tandem mass spectrometric determination of 3-hydroxypropylmercapturic acid in human urine.

Metabolism and Distribution of [2,3-14C]Acrolein in Sprague-Dawley Rats II. Identification of Urinary and Fecal Metabolites

Enhancement of the embryotoxicity of acrolein, but not phosphoramide mustard, by glutathione depletion in rat embryos in vitro

1. 3-Hydroxypropylmercapturic acid has been identified in the urine of rats dosed with cyclophosphamide, isophosphamide, and trilophosphamide and was isolated as its dicyclohexylammonium salt from the urine of rats dosed with cyclophosphamide.2. Rats excreted in their urine 55·5% of the 14C of an i.p. dose (200 mg/kg) of [4-14C]cyclophosphamide during the first 24 h after administration, and a further 6·6% during the subsequent 24 h. Of the total radioactivity excreted during the first 24 h, unchanged cyclophosphamide represented 19·3% or less, 41·6% was due to the major metabolite, carboxyphosphamide, and 3-hydroxypropylmercapturic acid represented 11·9%. The 14C label in the mercapturic acid was located in the S-substituent.3. 3-Hydroxypropylmercapturic acid was the only sulphur-containing metabolite of cyclophosphamide found in the blood and liver of rats, but 3-hydroxy[14C]propylmercapturic acid and S-(3-hydroxy[14C]propyl)-L-cysteine were tentatively identified in the bile of a rat dosed with [14C]cy...

The biosynthesis of 3-hydroxypropylmercapturic acid from cyclophosphamide.

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The biosynthesis of 3-hydroxypropylmercapturic acid from cyclophosphamide.