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Böhme, A.; Thaens, D.; Schramm, F.; Paschke, A.; Schüürmann, G. Thiol Reactivity and Its Impact on the Ciliate Toxicity of α,β-Unsaturated Aldehydes, Ketones, and Esters. Chem. Res. Toxicol. 2010, 23, 12, 1905–1912.

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Böhme, A.; Thaens, D.; Schramm, F.; Paschke, A.; Schüürmann, G. Thiol Reactivity and Its Impact on the Ciliate Toxicity of α,β-Unsaturated Aldehydes, Ketones, and Esters. Chem. Res. Toxicol. 2010, 23, 12, 1905–1912.

QDB archive DOI: 10.15152/QDB.15   DOWNLOAD

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Property logIGC50: 48-h Tetrahymena toxicity as log(IGC50) [log(mol/L)]

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  • Ruusmann, V. Data for: Thiol Reactivity and Its Impact on the Ciliate Toxicity of α,β-Unsaturated Aldehydes, Ketones, and Esters. QsarDB repository, QDB.15. 2012. http://dx.doi.org/10.15152/QDB.15

  • Böhme, A.; Thaens, D.; Schramm, F.; Paschke, A.; Schüürmann, G. Thiol Reactivity and Its Impact on the Ciliate Toxicity of α,β-Unsaturated Aldehydes, Ketones, and Esters. Chem. Res. Toxicol. 2010, 23, 1905–1912. http://dx.doi.org/10.1021/tx100226n

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dc.date.accessioned 2012-05-23T15:34:29Z
dc.date.available 2012-05-23T15:34:29Z
dc.date.issued 2012-05-23
dc.identifier.uri http://hdl.handle.net/10967/15
dc.identifier.uri http://dx.doi.org/10.15152/QDB.15
dc.description.abstract A recently introduced chemoassay has been used to determine second-order rate constants of the electrophile-nucleophile reaction of 15 α,β-unsaturated aldehydes with glutathione. The respective kGSH values vary for more than 3 orders of magnitude, and are within the range determined previously for 31 α,β-unsaturated ketones and esters. Structure-reactivity analyses yield distinct relationships between kGSH and structural features of the compounds. Moreover, increasing kGSH increases the aldehyde toxicity toward ciliates in terms of 48 h-EC50 values (effective concentration yielding 50% growth inhibition of Tetrahymena pyriformis within 48 h). A respective log-log regression equation including both kGSH and the octanol/water partition coefficient, Kow, yields a squared correlation coefficient of 0.96. Comparative analysis with corresponding data for 15 ketones and 16 esters reveals systematic differences between the three compound classes with regard to the individual contributions of hydrophobicity and electrophilic reactivity to aquatic toxicity. The former is particularly pronounced for aldehydes, while the ester toxicity is largely governed by reactivity, with ketones showing an intermediate pattern that is more similar to the one of esters than of aldehydes. It follows that within the Michael acceptor domain of α,β-unsaturated carbonyls, a distinction between aldehydes and nonaldehydic derivatives appears necessary when employing electrophilic reactivity as a component for the quantitative prediction of their reactive toxicity toward aquatic organisms.
dc.publisher Villu Ruusmann
dc.rights Attribution 4.0 International
dc.rights.uri http://creativecommons.org/licenses/by/4.0/
dc.title Böhme, A.; Thaens, D.; Schramm, F.; Paschke, A.; Schüürmann, G. Thiol Reactivity and Its Impact on the Ciliate Toxicity of α,β-Unsaturated Aldehydes, Ketones, and Esters. Chem. Res. Toxicol. 2010, 23, 12, 1905–1912.
qdb.property.endpoint 6. Other (Acute toxicity to ciliate protozoa)
qdb.property.species Tetrahymena pyriformis
qdb.descriptor.application KOWWIN 1.67
bibtex.entry article
bibtex.entry.author Böhme, A.
bibtex.entry.author Thaens, D.
bibtex.entry.author Schramm, F.
bibtex.entry.author Paschke, A.
bibtex.entry.author Schüürmann, G.
bibtex.entry.doi 10.1021/tx100226n
bibtex.entry.journal Chem. Res. Toxicol.
bibtex.entry.number 12
bibtex.entry.pages 1905–1912
bibtex.entry.title Thiol Reactivity and Its Impact on the Ciliate Toxicity of α,β-Unsaturated Aldehydes, Ketones, and Esters
bibtex.entry.volume 23
bibtex.entry.year 2010


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