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QSARs for the aquatic toxicity of aromatic aldehydes from Tetrahymena data [An article from: Chemosphere]
Book Details
Author(s)T.I. Netzeva, T.W. Schultz
PublisherElsevier
ISBN / ASINB000RR5J4S
ISBN-13978B000RR5J45
AvailabilityAvailable for download now
Sales Rank99,999,999
MarketplaceUnited States 🇺🇸
Description
This digital document is a journal article from Chemosphere, published by Elsevier in . The article is delivered in HTML format and is available in your Amazon.com Media Library immediately after purchase. You can view it with any web browser.
Description:
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 (logK"o"w), is the most important descriptor of aldehyde aquatic toxic potency. The model with logK"o"w was improved by adding electronic descriptor (the maximum acceptor superdelocalizability in a molecule-A"m"a"x) 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 (logK"o"w) and interaction with the biomacromolecules (A"m"a"x) 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/IGC"5"0)=0.540(0.038) logK"o"w+8.30(2.88)A"m"a"x-3.11(0.92), n=25, R^2=0.916, R"C"V^2=0.896, s=0.141, F=120], while the other aldehydes are modeled by the relationship [log(1/IGC"5"0)=0.583 (0.034)logK"o"w+9.80(2.62)A"m"a"x-4.04 (0.85), n=52, R^2=0.864, R"C"V^2=0.844, s=0.203, F=156], which is similar to the general benzene model.
Description:
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 (logK"o"w), is the most important descriptor of aldehyde aquatic toxic potency. The model with logK"o"w was improved by adding electronic descriptor (the maximum acceptor superdelocalizability in a molecule-A"m"a"x) 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 (logK"o"w) and interaction with the biomacromolecules (A"m"a"x) 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/IGC"5"0)=0.540(0.038) logK"o"w+8.30(2.88)A"m"a"x-3.11(0.92), n=25, R^2=0.916, R"C"V^2=0.896, s=0.141, F=120], while the other aldehydes are modeled by the relationship [log(1/IGC"5"0)=0.583 (0.034)logK"o"w+9.80(2.62)A"m"a"x-4.04 (0.85), n=52, R^2=0.864, R"C"V^2=0.844, s=0.203, F=156], which is similar to the general benzene model.
