Use of a (quantitative) structure-activity relationship [(Q)SAR] model to predict the toxicity of naphthenic acids
| Autor: | John V. Headley, Richard J. Kavanagh, Keith R. Solomon, Richard A. Frank, Hans Sanderson, B. Kent Burnison |
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| Rok vydání: | 2010 |
| Předmět: |
chemistry.chemical_classification
Quantitative structure–activity relationship Databases Factual Molecular Structure Health Toxicology and Mutagenesis Carboxylic acid Extraction (chemistry) Carboxylic Acids Quantitative Structure-Activity Relationship Toxicology Aliivibrio fischeri Models Biological Acute toxicity chemistry Daphnia Environmental chemistry Toxicity Proton NMR Oil sands Animals Microbial biodegradation Software |
| Zdroj: | Frank, R, Sanderson, H, Kavanagh, R, Burnison, K, Headley, J & Solomon, K 2010, ' Use of a (Quantitative) Structure-Activity Relationship [(Q)SAR] model to predict the toxicity of naphthenic acids ', Journal of Toxicology and Environmental Health. Part A, vol. 73, pp. 319-329 . https://doi.org/10.1080/15287390903421235 |
| ISSN: | 1528-7394 |
| DOI: | 10.1080/15287390903421235 |
| Popis: | Naphthenic acids (NAs) are a complex mixture of carboxylic acids that are natural constituents of oil sand found in north-eastern Alberta, Canada. NAs are released and concentrated in the alkaline water used in the extraction of bitumen from oil sand sediment. NAs have been identified as the principal toxic components of oil sands process-affected water (OSPW), and microbial degradation of lower molecular weight (MW) NAs decreases the toxicity of NA mixtures in OSPW. Analysis by proton nuclear magnetic resonance spectroscopy indicated that larger, more cyclic NAs contain greater carboxylic acid content, thereby decreasing their hydrophobicity and acute toxicity in comparison to lower MW NAs. The relationship between the acute toxicity of NAs and hydrophobicity suggests that narcosis is the probable mode of acute toxic action. The applicability of a (Quantitative) Structure-Activity Relationship ((Q)SAR) model to accurately predict the toxicity of NA-like surrogates was investigated. The USEPA’s ECOSAR model predicted the toxicity of NA-like surrogates with acceptable accuracy in comparison to observed toxicity values from Vibrio fischeri and Daphnia magna assays, indicating that the model has potential to serve as a prioritization tool for identifying NA structures likely to have an increased toxicity. Investigating NAs of equal MW, the ECOSAR model predicted increased toxic potency for NAs containing fewer carbon rings. Furthermore, NA structures with a linear grouping of carbon rings had a greater predicted toxic potency than structures containing carbon rings in a clustered grouping. |
| Databáze: | OpenAIRE |
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