Schultz, T.W.; Netzeva, T.I.; Roberts, D.W.; Cronin, M.T.D. Structure-Toxicity Relationships for the Effects to Tetrahymena pyriformis of Aliphatic, Carbonyl-Containing, α,β-Unsaturated Chemicals. Chem. Res. Toxicol. 2005, 18, 2, 330–341.

QsarDB Repository

Schultz, T.W.; Netzeva, T.I.; Roberts, D.W.; Cronin, M.T.D. Structure-Toxicity Relationships for the Effects to Tetrahymena pyriformis of Aliphatic, Carbonyl-Containing, α,β-Unsaturated Chemicals. Chem. Res. Toxicol. 2005, 18, 2, 330–341.

QDB archive DOI: 10.15152/QDB.14   DOWNLOAD

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

1: Aliphatic compounds

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Trainingtraining820.0151.046
2: α,β-unsaturated aldehydes

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Trainingtraining140.3791.197
3: α,β-unsaturated aldehydes

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Trainingtraining140.3011.182
4: α,β-unsaturated aldehydes

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Trainingtraining140.2291.294
5: α,β-unsaturated ketones

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Trainingtraining160.9280.260
6: Methacrylates

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Trainingtraining110.9250.262
7: Vinylene-containing esters

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Trainingtraining150.8140.247
8: Vinylene-containing esters

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Trainingtraining150.9340.147
9: Methacrylates and vinylene-containing esters

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Trainingtraining260.8850.252
10: Ethynylene-containing esters

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Trainingtraining100.9390.083

Citing

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

  • Ruusmann, V. Data for: Structure-Toxicity Relationships for the Effects to Tetrahymena pyriformis of Aliphatic, Carbonyl-Containing, α,β-Unsaturated Chemicals. QsarDB repository, QDB.14. 2012. http://dx.doi.org/10.15152/QDB.14

  • Schultz, T. W.; Netzeva, T. I.; Roberts, D. W.; Cronin, M. T. D. Structure-Toxicity Relationships for the Effects to Tetrahymena pyriformis of Aliphatic, Carbonyl-Containing, α,β-Unsaturated Chemicals. Chem. Res. Toxicol. 2005, 18, 330–341. http://dx.doi.org/10.1021/tx049833j

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Title: Schultz, T.W.; Netzeva, T.I.; Roberts, D.W.; Cronin, M.T.D. Structure-Toxicity Relationships for the Effects to Tetrahymena pyriformis of Aliphatic, Carbonyl-Containing, α,β-Unsaturated Chemicals. Chem. Res. Toxicol. 2005, 18, 2, 330–341.
Abstract:Toxicity data for 82 aliphatic chemicals with an alpha,beta-unsaturated substructure were compiled. Toxicity was assessed in the 2-day Tetrahymena pyriformis population growth impairment assay. Toxic potency [log(IGC50(-1))] for most of these chemicals was in excess of baseline narcosis as quantified by the 1-octanol/water partition coefficient (log K(ow)). The toxicity of the alpha,beta-unsaturated aldehydes was modeled well by log K(ow) in conjunction with the sum of partial charges on the vinylene carbon atoms (Q(C4) + Q(C3)) and the energy of the lowest unoccupied molecular orbital (E(lumo)). These electronic descriptors were also successful at modeling the toxicity of alpha,beta-unsaturated ketones. The toxicity of a range of acrylates was constant within about 0.2 of a log unit. Conversely, the toxicity of methacrylates and esters containing the vinylene group varied considerably and was explained by their hydrophobicity. The comparison of the quantitative structure-activity relationship (QSAR) for the methacrylates and esters with that for non-polar narcosis showed little significant difference and hence suggested that substitution on the carbon-carbon double bond in the methacrylates and vinylene unsaturated esters does not enhance toxicity over that of baseline. Substitution on the carbon-carbon double bond in the alpha,beta-unsaturated aldehydes resulted in toxicity that was similar to that for saturated derivatives. Although an excellent hydrophobicity-dependent QSAR was developed for the esters containing ethynylene group, these compounds are considered to act as Michael-type acceptors. Attempts to combine different groups of Michael-type acceptors into a single QSAR, based on mechanistically derived descriptors, were unsuccessful. Thus, the modeling of the toxicity of the alpha,beta-unsaturated carbonyl domain is currently limited to models for narrow subdomains.
URI:http://hdl.handle.net/10967/14
http://dx.doi.org/10.15152/QDB.14
Date:2012-05-23


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