Quantitative structure-activity relationships for estrogen receptor   binding affinity of phenolic chemicals

doi:10.1016/S0043-1354(02)00378-0

CORC > 北京大学 > 城市与环境学院

	Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals
	Hu, JY ; Aizawa, T
刊名	水研究
	2003
关键词	QSAR binding affinity phenolic compounds endocrine disruption quantum chemical modeling POLYCHLORINATED HYDROXYBIPHENYLS ALKYLPHENOLIC COMPOUNDS ESTRADIOL XENOESTROGENS SUBSTANCES CELLS
DOI	10.1016/S0043-1354(02)00378-0
英文摘要	The estrogen receptor (ER) binding affinities of 25 compounds including 15 industrial phenolic chemicals, two phytoestrogens, three natural steroids and one man-made steroid were detected by a binding competition assay. The 17 industrial phenolic chemicals were selected as objective compounds because they are possibly released from epoxy and polyester-styrene resins used in lacquer coatings of concrete tank and lining of steel pipe in water supply system. A quantitative structure-activity relationship (QSAR) for structurally diverse phenols, nine alkylphenols with only one alkyl group, four hydroxyl biphenyls, bisphenol A and four natural and man-made estrogens was established by applying a quantum chemical modeling method. Logarithm of octanol-water coefficient (log Pow), molecular volume (V(m)), and energies of the highest occupied molecular orbital (epsilon(HOMO)) and lowest unoccupied molecular orbital (epsilon(LUMO)) were selected as hydrophobic, steric (V(m)), and electronic chemical descriptors, respectively. Chemicals capable of ER binding had large V(m) and high epsilon(HOMO), while the effects of log Pow and epsilon(LUMO) on the binding affinity could not be identified. The QSAR made successful predictions for the three phytoestrogens. Also, the successful prediction of ER-binding affinity for biochanin A, another phytoestrogen, two indicators of pH (phenolphthalin and phenolphthalein) and one alkylphenolic chemical with three alkyl groups (4-methyl-2,6-di-butyl-phenol), by amending the V(m) in the above-mentioned QSAR according to the electron-density distribution (or HOMO density) is an additional step in the elucidation of chemical steric and electronic parameters for predicting the binding affinities of phenolic compounds. (C) 2003 Elsevier Science Ltd. All rights reserved.; Engineering, Environmental; Environmental Sciences; Water Resources; SCI(E); EI; PubMed; 76; ARTICLE; 6; 1213-1222; 37
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/160766]
专题	城市与环境学院
推荐引用方式 GB/T 7714	Hu, JY,Aizawa, T. Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals[J]. 水研究,2003.
APA	Hu, JY,&Aizawa, T.(2003).Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals.水研究.
MLA	Hu, JY,et al."Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals".水研究 (2003).