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Schultz, T.W.; Sparfkin, C.L.; Aptula, A.O. Reactivity-based toxicity modelling of five-membered heterocyclic compounds: Application to Tetrahymena pyriformis. SAR QSAR Environ. Res. 2010, 7, 8, 681–691.

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Schultz, T.W.; Sparfkin, C.L.; Aptula, A.O. Reactivity-based toxicity modelling of five-membered heterocyclic compounds: Application to Tetrahymena pyriformis. SAR QSAR Environ. Res. 2010, 7, 8, 681–691.

QDB archive DOI: 10.15152/QDB.77   DOWNLOAD

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Property pIGC50: 40-h Tetrahymena toxicity as log(1/IGC50) [log(L/mmol)]

1: Michael acceptors

Regression model (regression)

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Name Type n

R2

σ

Training training 23 0.815 0.400

Property MOA: Mode of action

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When using this QDB archive, please cite (see details) it together with the original article:

  • Ruusmann, V. Data for: Reactivity-based toxicity modelling of five-membered heterocyclic compounds: Application to Tetrahymena pyriformis. QsarDB repository, QDB.77. 2012. http://dx.doi.org/10.15152/QDB.77

  • Schultz, T. W.; Sparfkin, C. L.; Aptula, A. O. Reactivity-based toxicity modelling of five-membered heterocyclic compounds: Application to Tetrahymena pyriformis. SAR QSAR Environ. Res. 2010, 7, 681–691. http://dx.doi.org/10.1080/1062936X.2010.528933

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dc.date.accessioned 2012-05-23T16:09:15Z
dc.date.available 2012-05-23T16:09:15Z
dc.date.issued 2012-05-23
dc.identifier.uri http://hdl.handle.net/10967/77
dc.identifier.uri http://dx.doi.org/10.15152/QDB.77
dc.description.abstract A diverse set of 57 heterocyclic organic chemicals, consisting of a five-membered unsaturated ring of four carbon atoms and one oxygen (furans), or sulfur (thiophenes), or nitrogen (pyrroles) were evaluated for reactivity with thiol and acute aquatic toxicity assays using glutathione (GSH) as a model nucleophile and the ciliate Tetrahymena pyriformis, respectively. Reactivity was quantified by the RC₅₀ value, the concentration of test compound that produced 50% reaction of the GSH thiol groups in 2 hours. Under standard conditions, RC₅₀ values are mathematically proportional to reciprocal rate constants. Toxicity was quantified by the IGC₅₀, the concentration of the test compound that produces 50% inhibition of population growth in 40 hours. Pyrroles with polarized α,β-unsaturated substructures were found to be non-reactive with GSH and did not exhibit excess toxicity in the Tetrahymena assay. In contrast, those furans and thiophenes with polarized α,β-unsaturated substructures were reactive with GSH via the Michael addition mechanism and did exhibit excess acute aquatic toxicity in Tetrahymena. For furans and thiophenes, reactivity and toxicity varied with the number, type, and location on the ring of the π-bond-containing polarized moieties. Comparisons of reactivity and toxicity potency between furan and thiophene derivatives revealed furans to be twice as potent as thiophenes. QSAR analysis revealed that aquatic toxicity IGC₅₀ to Tetrahymena is correlated with RC₅₀ values: log (IGC₅₀(-1)) = 1.13 log (RC₅₀(-1)) + 1.43; n = 23, r²= 0.815, r²(adj) = 0.806, s = 0.41, F = 92.
dc.publisher Villu Ruusmann
dc.rights Attribution 4.0 International
dc.rights.uri http://creativecommons.org/licenses/by/4.0/
dc.title Schultz, T.W.; Sparfkin, C.L.; Aptula, A.O. Reactivity-based toxicity modelling of five-membered heterocyclic compounds: Application to Tetrahymena pyriformis. SAR QSAR Environ. Res. 2010, 7, 8, 681–691.
qdb.property.endpoint 6. Other (Acute toxicity to ciliate protozoa)
qdb.property.species Tetrahymena pyriformis
qdb.descriptor.application KOWWIN
bibtex.entry article
bibtex.entry.author Schultz, T. W.
bibtex.entry.author Sparfkin, C. L.
bibtex.entry.author Aptula, A. O.
bibtex.entry.doi 10.1080/1062936X.2010.528933
bibtex.entry.journal SAR QSAR Environ. Res.
bibtex.entry.number 8
bibtex.entry.pages 681–691
bibtex.entry.title Reactivity-based toxicity modelling of five-membered heterocyclic compounds: Application to Tetrahymena pyriformis
bibtex.entry.volume 7
bibtex.entry.year 2010
qdb.model.type Regression model (regression)


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