Genotoxicity of quinolones: Substituents contribution and transformation products QSAR evaluation Using 2D and 3D models

CORC > 生态环境研究中心 > 中国科学院生态环境研究中心 > 环境化学与生态毒理学国家重点实验室

	Genotoxicity of quinolones: Substituents contribution and transformation products QSAR evaluation Using 2D and 3D models
	Li, Min ; Wei, Dongbin ; Zhao, Huimin ; Du, Yuguo
刊名	CHEMOSPHERE
	2014
卷号	95 期号:1 页码:220-226
关键词	Quinolone Genotoxicity QSAR CoMFA
ISSN号	0045-6535
中文摘要	The genotoxicity of 21 quinolones antibiotics was determined using SOS/umu assay. Some quinolones exhibited high genotoxicity, and the chemical substituent on quinolone ring significantly affected genotoxicity. To establish the relationship between genotoxicity and substituent, a 2D-QSAR model based on quantum chemical parameters was developed. Calculation suggested that both steric and electrostatic properties were correlated well with genotoxicity. Furthermore, the specific effect on three key active sites (1-, 7- and 8-positions) of quinolone ring was investigated using a 3D-QSAR (comparative molecular field analysis, CoMFA) method. From our modeling, the genotoxicity increased when substituents had: (1) big volume and/or positive charge at 1-position; (2) negative charge at 7-position; and (3) small volume and/or negative charge at 8-position. The developed QSAR models were applicable to estimate genotoxicity of quinolones antibiotics and their transformation products. It is noted that some of the transformation products exhibited higher genotoxicity comparing to their precursor (e.g., ciprofloxacin). This study provided an alternative way to understand the molecule genotoxicity of quinolones derivatives, as well as to evaluate their potential environmental risks. (C) 2013 Elsevier Ltd. All rights reserved.
WOS记录号	WOS:000328868400031
公开日期	2015-03-24
内容类型	期刊论文
源URL	[http://ir.rcees.ac.cn/handle/311016/9372]
专题	生态环境研究中心_环境化学与生态毒理学国家重点实验室生态环境研究中心_中国科学院环境生物技术重点实验室
推荐引用方式 GB/T 7714	Li, Min,Wei, Dongbin,Zhao, Huimin,et al. Genotoxicity of quinolones: Substituents contribution and transformation products QSAR evaluation Using 2D and 3D models[J]. CHEMOSPHERE,2014,95(1):220-226.
APA	Li, Min,Wei, Dongbin,Zhao, Huimin,&Du, Yuguo.(2014).Genotoxicity of quinolones: Substituents contribution and transformation products QSAR evaluation Using 2D and 3D models.CHEMOSPHERE,95(1),220-226.
MLA	Li, Min,et al."Genotoxicity of quinolones: Substituents contribution and transformation products QSAR evaluation Using 2D and 3D models".CHEMOSPHERE 95.1(2014):220-226.