文献类型： 外文期刊

作者： Wang Cui-Hua ² ; Jiang Mei ² ; Li Xiao-Lin ³ ; Shen Xin-Qiang ² ; Yu Hong-Xia ³ ; Wu Yang ¹ ;

作者机构： 1.Gen Off Lake Taihu Water Pollut Prevent & Control, Nanjing 210024, Jiangsu, Peoples R China

2.Chinese Acad Fisheries Sci, E China Sea Fisheries Res Inst, Shanghai 200090, Peoples R China

3.Nanjing Univ, State Key Lab Pollut Control & Resources Reuse, Nanjing 210093, Jiangsu, Peoples R China

关键词： aromatic hydrocarbons;larval Sinonvaculina constricta;acute toxicity;CoMSIA;MLR

期刊名称：CHINESE JOURNAL OF STRUCTURAL CHEMISTRY （ 影响因子：0.893； 五年影响因子：0.603 ）

ISSN： 0254-5861

年卷期： 2012 年 31 卷 3 期

页码：

收录情况： SCI

摘要： Aromatic hydrocarbons, one of the persistent organic pollutants (POPs), has been usually found in mussels, accumulated for their hard mobility and activities in harbours and estuaries. In this study, based on the 96 hr-LC50 of 12 aromatic hydrocarbons with larval sinonvaculina constricta, three-dimensional quantitative structure-activity relationship (3D-QSAR) technique: comparative molecular similarity indices analysis (CoMSIA) and 2D-QSAR technique: multiple linear regression (MLR) were described to obtain more detailed insight into the structure-activity relationships between the molecular structure and bio-activity. The results show the MLR model based on density functional theory (DFT) calculation carried out at the B3LYP/6-311** level with Gaussian 03 program yielded a very good correlation with a coefficient squared R-2 of 0.716 and a cross-validated Q(2) of 0.874. The dipole moment and enthalpy, as the thermodynamic parameters, were two important factors influencing pLC(50). Correspondingly, CoMSIA based on the partial least-squares (PLS) methodology with steric, electrostatic, hydrophobic, H-bond donor and acceptor fields contributing simultaneously were employed and the values of R-2 and the cross validation with leave-One-Out (LOO) Q(LOO)(2) were 0.585 and 0.990, respectively, which reveals the structure features, such as the electronegative substituent (nitro-group), hydrophobic groups (the benzene ring) and H-bond (nitro-group), related to the toxicity. The results of 2D-QSAR employing MLR model and 3D-QSAR employing CoMSIA model provide the useful information for predicting the toxicity of other aromatic hydrocarbons by comparing the molecular structures of similar compounds.