QSARs for the aquatic toxicity of aromatic aldehydes from Tetrahymena data
| Autor: | T. Wayne Schultz, Tatiana I. Netzeva |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
Quantitative structure–activity relationship
Environmental Engineering Stereochemistry Health Toxicology and Mutagenesis Quantitative Structure-Activity Relationship Biology Aldehyde Aquatic toxicology chemistry.chemical_compound Computational chemistry Toxicity Tests Animals Environmental Chemistry Benzene Biotransformation chemistry.chemical_classification Aldehydes Cell Membrane Quinones Public Health Environmental and Occupational Health Tetrahymena General Medicine General Chemistry biology.organism_classification Pollution Acute toxicity Partition coefficient Models Chemical chemistry Tetrahymena pyriformis Water Pollutants Chemical |
| Zdroj: | Chemosphere. 61:1632-1643 |
| ISSN: | 0045-6535 |
| DOI: | 10.1016/j.chemosphere.2005.04.040 |
| Popis: | The aim of the study was to develop quantitative structure–activity relationships (QSARs) for a large group of 77 aromatic aldehydes tested for acute toxicity to the ciliate Tetrahymena pyriformis using mechanistically interpretable descriptors. The resulting QSARs revealed that the 1-octanol/water partition coefficient (log Kow), is the most important descriptor of aldehyde aquatic toxic potency. The model with log Kow was improved by adding electronic descriptor (the maximum acceptor superdelocalizability in a molecule—Amax) based on calculations with the semi-empirical AM1 model. The two descriptors reflect the two main processes responsible for demonstration of acute aquatic toxicity, namely penetration through cell membranes (log Kow) and interaction with the biomacromolecules (Amax) into the cells. Results showed that generally the studied group of aldehydes could be modeled by this simple two-descriptor approach. However, the group of 2- and/or 4-hydroxylated aldehydes demonstrates enhanced toxicity compared to the other aldehydes. Transformation to quinone-like structures is proposed as the explanation for this enhanced potency. The 2- and/or 4-hydroxylated aldehydes are modeled successfully by [log(1/IGC50) = 0.540(0.038) log Kow + 8.30(2.88)Amax − 3.11(0.92), n = 25, R2 = 0.916, R CV 2 = 0 . 896 , s = 0.141, F = 120], while the other aldehydes are modeled by the relationship [log(1/IGC50) = 0.583 (0.034)log Kow + 9.80(2.62)Amax − 4.04 (0.85), n = 52, R2 = 0.864, R CV 2 = 0 . 844 , s = 0.203, F = 156], which is similar to the general benzene model. |
| Databáze: | OpenAIRE |
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