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Yarbrough, J.W.; Schultz, T.W. Abiotic Sulfhydryl Reactivity: A Predictor of Aquatic Toxicity for Carbonyl-Containing α,β-Unsaturated Compounds. Chem. Res. Toxicol. 2007, 20, 3, 558–562.

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Yarbrough, J.W.; Schultz, T.W. Abiotic Sulfhydryl Reactivity: A Predictor of Aquatic Toxicity for Carbonyl-Containing α,β-Unsaturated Compounds. Chem. Res. Toxicol. 2007, 20, 3, 558–562.

QDB archive DOI: 10.15152/QDB.16   DOWNLOAD

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Property IGC50: 40-h Tetrahymena toxicity as IGC50 [mmol/L]

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  • Ruusmann, V. Data for: Abiotic Sulfhydryl Reactivity: A Predictor of Aquatic Toxicity for Carbonyl-Containing α,β-Unsaturated Compounds. QsarDB repository, QDB.16. 2012. http://dx.doi.org/10.15152/QDB.16

  • Yarbrough, J. W.; Schultz, T. W. Abiotic Sulfhydryl Reactivity: A Predictor of Aquatic Toxicity for Carbonyl-Containing α,β-Unsaturated Compounds. Chem. Res. Toxicol. 2007, 20, 558–562. http://dx.doi.org/10.1021/tx600344a

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dc.date.accessioned 2012-05-23T15:35:02Z
dc.date.available 2012-05-23T15:35:02Z
dc.date.issued 2012-05-23
dc.identifier.uri http://hdl.handle.net/10967/16
dc.identifier.uri http://dx.doi.org/10.15152/QDB.16
dc.description.abstract A diverse series of aliphatic alpha,beta-unsaturated esters, ketones, and aldehydes were evaluated for reactivity with the model nucleophile sulfhydryl group in the form of the cysteine residue of the tripeptide glutathione; the reactive end point (RC50) was then related to aquatic toxicity (IGC50) assessed in the Tetrahymena pyriformis population growth impairment assay. The substructure specific to all tested reactive substances, an olefin conjugated to a carbonyl group, is inherently electrophilic and conveys the potential to act by way of Michael-type nucleophilic addition. All such unsaturated compounds are inherently acutely toxic. However, their toxicity is difficult to model with conventional descriptors since toxicity is independent of both hydrophobicity and molecular orbital electrophilicity but dependent on the specific molecular structure. While methacrylates typically did not attain an RC50 value at saturation, a linear relationship [log (IGC50(-1)) = 0.936[log (RC50(-1))] + 0.508, where n = 41, r2 = 0.846, q2 = 0.832, s = 0.35, F = 214, and Pr > F = 0.0001] was observed between aquatic toxicity and reactivity for the other carbonyl-containing alpha,beta-unsaturated chemicals.
dc.publisher Villu Ruusmann
dc.rights Attribution 4.0 International
dc.rights.uri http://creativecommons.org/licenses/by/4.0/
dc.title Yarbrough, J.W.; Schultz, T.W. Abiotic Sulfhydryl Reactivity: A Predictor of Aquatic Toxicity for Carbonyl-Containing α,β-Unsaturated Compounds. Chem. Res. Toxicol. 2007, 20, 3, 558–562.
qdb.property.endpoint 6. Other (Acute toxicity to ciliate protozoa)
qdb.property.species Tetrahymena pyriformis
bibtex.entry article
bibtex.entry.author Yarbrough, J. W.
bibtex.entry.author Schultz, T. W.
bibtex.entry.doi 10.1021/tx600344a
bibtex.entry.journal Chem. Res. Toxicol.
bibtex.entry.number 3
bibtex.entry.pages 558–562
bibtex.entry.title Abiotic Sulfhydryl Reactivity: A Predictor of Aquatic Toxicity for Carbonyl-Containing α,β-Unsaturated Compounds
bibtex.entry.volume 20
bibtex.entry.year 2007


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