Quantitative Structure−Activity Relationship Models for Prediction of the Toxicity of Polybrominated Diphenyl Ether Congeners

Levels of polybrominated diphenyl ethers (PBDEs) are increasing in the environment and may cause long-term health problems in humans. The similarity in the chemical structures of PBDEs and other halogenated aromatic pollutants hints on the possibility that they might share similar toxicological effe...

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Bibliographic Details
Published in:Environmental science & technology 2005-07, Vol.39 (13), p.4961-4966
Main Authors: Wang, Yawei, Liu, Huanxiang, Zhao, Chunyan, Liu, Hanxia, Cai, Zongwei, Jiang, Guibin
Format: Article
Language:English
Subjects:
Biological and medical sciences
Environmental Pollutants - toxicity
Environmental pollutants toxicology
Ethers - chemistry
Ethers - toxicity
General aspects
Medical sciences
Models, Theoretical
Pollutants
Polybrominated Biphenyls - toxicity
Polybrominated diphenyl ethers
Predictions
Quantitative Structure-Activity Relationship
Static Electricity
Toxicity
Toxicology
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Summary:Levels of polybrominated diphenyl ethers (PBDEs) are increasing in the environment and may cause long-term health problems in humans. The similarity in the chemical structures of PBDEs and other halogenated aromatic pollutants hints on the possibility that they might share similar toxicological effects. In this work, three-dimensional quantitative structure activity relationships (3-D-QSAR) models, using comparative molecular field analysis (CoMFA) and comparative similarity indices analysis (CoMSIA), were built based on calculated structural indices and a reported experimental toxicology index (aryl hydrocarbon receptor relative binding affinities, RBA) of 18 PBDEs congeners, to determine the factors required for the RBA of these PBDEs. After performing leave-one-out cross-validation, satisfactory results were obtained with cross-validation Q 2 and R 2 values of 0.580 and 0.995 by the CoMFA model and 0.680 and 0.982 by the CoMSIA model, respectively. The results showed clearly that the nonplanar conformations of PBDEs result in the lowest energy level and that the electrostatic index was the main factor reflecting the RBA of PBDEs. The two QSAR models were then used to predict the RBA value of 46 PBDEs for which experimental values are unavailable at present.
ISSN:0013-936X
1520-5851
DOI:10.1021/es050017n