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Vol. 27 No. 2 (2015): Vol 27 Issue 2

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Investigation on Aryl Hydrocarbon Receptor Binding Affinity QSAR Model of Polybrominated Diphenyl Ethers Based on Substituent Descriptors/Quantum Chemical Parameters

https://doi.org/10.14233/ajchem.2015.17042
Long Jiang
Resources and Environmental Research Academy, North China Electric Power University, P.O. Box 58, Beijing 102206, P.R. China
Jingya Wen
Resources and Environmental Research Academy, North China Electric Power University, P.O. Box 58, Beijing 102206, P.R. China
Yaling Zeng
Resources and Environmental Research Academy, North China Electric Power University, P.O. Box 58, Beijing 102206, P.R. China
Yu Li
Resources and Environmental Research Academy, North China Electric Power University, P.O. Box 58, Beijing 102206, P.R. China

Corresponding Author(s) : Yu Li

liyuxx8@hotmail.com

Asian Journal of Chemistry, Vol. 27 No. 2 (2015): Vol 27 Issue 2

Abstract

In this paper, 21 quantum chemical parameters (charge parameters, energy parameters, polarization parameters) and 13 substituent descriptors (total number of substituents, substituents in different position, substituent positional relationship parameters, substituents difference between two rings) of 17 polybrominated diphenyl ethers were selected as the independent variables, the binding ability to aryl hydrocarbon receptor defined as dependent variable. Then, the QSAR model of polybrominated diphenyl ethers aryl hydrocarbon receptor binding affinities was established based on above-mentioned substituent descriptors/quantum chemical parameters to predict the binding affinities of unknown polybrominated diphenyl ethers, analyze the aryl hydrocarbon receptor binding mechanism from views of substituent pattern and quantum chemical parameters respectively, identify the aryl hydrocarbon receptor binding affinity level of each congener. The results showed that the aryl hydrocarbon receptor binding affinities of polybrominated diphenyl ethers were affected by Br substituent in each position significantly, not correlated with the total bromine and difference brominates type between two ring markedly. Among the quantum chemical parameters, qH+, q-, Da and axx were the critical variables which effected the aryl hydrocarbon receptor binding affinity of polybrominated diphenyl ethers importantly, reflecting the binding affinity was main dominated by electrostatic force, polybrominated diphenyl ethers with symmetrical charge distribution, had small the molecular polarity and aryl hydrocarbon receptor binding affinity. The established QSAR model for polybrominated diphenyl ethers aryl hydrocarbon receptor binding affinity, with the simulation and prediction coefficients were 0.928 and 0.828, respectively, indicating good fitting and predicted ability, was to predict aryl hydrocarbon receptor binding affinities of other unknown polybrominated diphenyl ether congeners and identify binding level. The aryl hydrocarbon receptor binding affinities of polybrominated diphenyl ethers performed small relatively compared with dioxin, between them there were 13 congeners with medium aryl hydrocarbon receptor binding affinity, 188 congeners with low aryl hydrocarbon receptor binding affinity and only BDE-85 with high aryl hydrocarbon receptor binding affinity. This study may provide theoretical guidance to carry out more targeted control efforts for polybrominated diphenyl ethers' biological toxicity.

Keywords

Quantum chemical calculation Substituent descriptors Polybrominated diphenyl ethers QSAR
Jiang, L., Wen, J., Zeng, Y., & Li, Y. (2015). Investigation on Aryl Hydrocarbon Receptor Binding Affinity QSAR Model of Polybrominated Diphenyl Ethers Based on Substituent Descriptors/Quantum Chemical Parameters. Asian Journal of Chemistry, 27(2), 575–581. https://doi.org/10.14233/ajchem.2015.17042
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