[1]李鸣建,陈 艳,冯长君.马来酸酯类化合物结构与抑菌活性 密度泛函理论研究[J].南京理工大学学报(自然科学版),2014,38(05):695-700.
 Li Mingjian,Chen Yan,Feng Changjun.Structure-antibacterial activity relationship of maleic ether compound by density functional theory[J].Journal of Nanjing University of Science and Technology,2014,38(05):695-700.
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马来酸酯类化合物结构与抑菌活性 密度泛函理论研究
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《南京理工大学学报》(自然科学版)[ISSN:1005-9830/CN:32-1397/N]

卷:
38卷
期数:
2014年05期
页码:
695-700
栏目:
出版日期:
2014-10-29

文章信息/Info

Title:
Structure-antibacterial activity relationship of maleic ether compound by density functional theory
作者:
李鸣建陈 艳冯长君
徐州工程学院 化学化工学院,江苏 徐州 221111
Author(s):
Li MingjianChen YanFeng Changjun
School of Chemistry and Chemical Engineering,Xuzhou Institute of Technology,Xuzhou 221111,China
关键词:
计算化学 马来酸酯 抑菌活性 油菜菌核病菌 密度泛函理论 构效关系
Keywords:
computational chemistry maleic ether antibacterial activity sclerotinia sclerotiorum density functional theory quantitative structure-activity relationship
分类号:
S482.2; O6-051
摘要:
采用量子化学密度泛函理论(DFT)研究马来酸酯类化合物对油菜菌核病菌抗菌活性EM50的构效关系(QSAR)。在DFT-B3LYP方法及基组6-31G(d)水平下,对14种马来酸酯类化合物分子进行几何及电子结构全优化,选择最高占据轨道能EHOMO,次最高占据轨道能ENHOMO,最低空轨道能ELUMO,次最低空轨道能ENLUMO,分子中原子的净电荷QZ,偶极矩μ,零点振动能Ev,分子总能量E,热容Cv和熵Sm等作为量子化学描述符qL通过最佳变量子集回归分析筛选出影响EM50的主要因素,并建立了QSAR模型。通过留一法交叉分析和方差膨胀因子法检测发现,模型具有良好的稳定性及预测能力。拟合的判定系数R2及交叉验证系数R2cv分别为0.910,0.818。分析结果表明,EHOMO和O7原子上净电荷QO7是影响油菜菌核病菌抗菌活性的主要因素。EHOMO越高,抑菌活性越强; QO7越大,抑菌活性越弱。该文QSAR模型可为设计具有高抑菌活性的马来酸酯类化合物提供理论参考。
Abstract:
The density functional theory(DFT)method of quantum chemistry is used to study the quarititative structure-activity relationship(QSAR)of the antibacterial activities EM50 of 14 maleic ether compounds to sclerotinia sclerotiorum.The DFT-B3LYP method with the basic set 6-31G(d)is employed to calculate the molecular geometries and electronic structures of 14 maleic ether molecules.The energy of the highest occupied molecular orbital EHOMO,the energy of the lowest unoccupied molecular orbital ELUMO,the energy of the next lowest unoccupied molecular orbital ENHOMO,the energy of the next highest occupied molecular orbital ENLUMO,the net charge of atoms in molecules QZ,the dipole moment μ,the vibrational energy at OK Ev,the total energy E,the heat capacity Cv and the entropy Sm are selected as structural descriptors qL.The main independent factors affecting the antibacterial activities EM50 is determined by leaps-and-bounds regression analysis,and then satisfactory QSAR model is established.The good stability and predictive ability of the model are examined by the leave-one-out(LOO)cross-validation method and variance inflation factors VIF.The fitting correlation coefficient R2 and the cross-validation coefficient R2cv are 0.910 and 0.818,respectively.The result suggests that the energy of highest occupied molecular orbital EHOMO and the net charge QO7 of O7 atom are the predominant factors affecting the antibacterial activity against sclerotinia sclerotiorum.The antibacterial activity of the compounds increase with the increase of the EHOMO; however,the higher the QO7 is,the lower the antibacterial activity is.The models may be used as the theoretical reference for the design of new maleic ether compounds with high antibacterial activities.

参考文献/References:

[1] 胡辰尧,王涛,居学海,等.杂环芳胺结构与致癌性和致突性的密度泛函研究[J].南京理工大学学报,2012,36(2):348-352. Hu Chenyao,Wang Tao,Ju Xuehai,et al.Density functional study of relationship between structure and carcinogenicity/mutagenicity of heterocyclic aromatic amines[J].Journal of Nanjing University of Science and Technology,2012,36(2):348-352.
[2]石文艳,吕志敏,雷武,等.两种荧光染料的合成及其量子化学研究[J].南京理工大学学报,2011,35(6):867-872. Shi Wenyan,Lv Zhimin,Lei Wu,et al.Synthesis and quantum chemistry study of two fluorescent dyes[J].Journal of Nanjing University of Science and Technology,2011,35(6):867-872.
[3]Levet A,Bordes C,Clément Y,et al.Quantitative structure-activity relationship to predict acute fish toxicity of organic solvents[J].Chemosphere,2013,93(6):1094-1103.
[4]Bhaarathi Natarajan,Luigi Genovese,Mark E Casida,et al.Wavelet-based linear-response time-dependent density-functional theory[J].Chemical Physics,2012,402(19):29-40.
[5]Feng Changjun,Yang Weihua.Linear QSAR regression models for the prediction of bioconcentration factors of chloroanitines in fish by density functional theory[J].Chin J Struct Chem,2014,33(6):830-834.
[6]冯长君,堵锡华,沐来龙.用新型连接性指数与神经网络预测取代苯酚和取代苯甲酸生物降解性[J].南京理工大学学报,2009,33(5):700-706. Feng Changjun,Du Xihua,Mu Lailong.Prediction of biodegradability of substituted phenols and benzoic acids with novel molecular connectivity index and artificial neural network[J].Journal of Nanjing University of Science and Technology,2009,33(5):700-706.
[7]冯长君,杨伟华,沐来龙.硝基芳烃对呆鲦鱼急性毒性的CoMFA研究[J].南京理工大学学报,2008,32(1):642-645. Feng Changjun,Yang Weihua,Mu Lailong.Acute toxicity of nitroaromatic compounds to pimephales with CoMFA[J].Journal of Nanjing University of Science and Technology,2008,32(1):642-645.
[8]李鸣建,冯长君,蔡可迎.电性距离矢量预测有机污染物的生物富集因子[J].北京理工大学学报,2011,31(12):1469-1474. Li Mingjian,Feng Changjun,Cai Keying.Estimation and prediction of bioconcentration factors of nonionic organic compounds in fish by electronegativity-distance vector[J].Transactions of Beijing Institute of Technology,2011,31(12):1469-1474.
[9]陈艳,堵锡华.Dragon软件用于黄酮类化合物抗氧化活性的预测[J].科技通报,2012,28(1):30-33. Chen Yan,Du Xihua.Predicting antioxidant activity of flavonoids with Dragon software[J].Bulletin of Science and Technology,2012,28(1):30-33.
[10]李鸣建,冯长君.新三取代嘧啶苯磺酰脲衍生物除草活性的QSAR[J].华中科技大学学报(自然科学版),2011,39(3):128-132. Li Mingjian,Feng Changjun.Study of the QSAR of the herbicidal activity of new trisubstituted pyrimidine phenylsulfonylurea derivatives[J].J Huazhong Univ of Sci & Tech(Natural Science Edition),2011,39(3):128-132.
[11]陶婉君,李沉纹,尹宗宁.基于定量构效关系设计自乳化系统[J].物理化学学报,2011,27(1):71-77. Tao Wangjun,Li Chenwen,Yin Zongning.Design of self-emulsifying system based on QSAR[J].Acta Phys Chim Sin,2011,27(1):71-77.
[12]芮云锋,陈小龙,熊智强,等.马来酸酯类物质的合成及其抑菌活性研究[J].浙江农业科学,2011,4:871-874. Rui Yunfeng,Chen Xiaolong,Xiong Zhiqiang,et al.Study on synthesis and antifungal activity of maleic ether compounds[J].J Zhejiang Agric Sci,2011,4:871-874.
[13]Douglas M H,Subhash C B,Denise M.Assessing model fit by cross-validation[J].J Chem Inf Comput Sci,2003,43:579-586.
[14]Winkler D A,Burden F R.Holographic QSAR of benzodiazepines[J].Quant Struct-act Relat,1998,17:224-231.
[15]Wei Dongbin,Zhang Aiqian,Wu Chunde,et al.Rogressive study and robustness test of QSAR model based on quantum chemical parameters for predicting BCF of selected polychlorinated organic compounds[J].Chemosphere,2001,44(6):1421-1428.
[16]Urra L S,Gonza'lez M P,Teijeira M.2D-autocorrelation descriptors for predicting cytotoxicity of naphthoquinone ester derivatives against oral human epidermoid carcinoma[J].Bioorganic and Medicinal Chemistry,2007,15(10):3565-3571.
[17]Urra L S,Gonza'lez M P,Teijeira M.QSAR studies about cytotoxicity of benzophenazines with dual inhibition toward both topoisomerasesⅠand Ⅱ:3D-MoRSE descriptors and statistical considerations about variable selection[J].Bioorganic & Medicinal Chemistry,2006,14(21):7347-7358.
[18]Yao S W,Lopes V H C,Fernández F,et al.Synthesis and QSAR study of the anticancer activity of some novel indane carbocyclic nucleosides[J].Bioorg Med Chem,2003,11(23):4999-5006.

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备注/Memo

备注/Memo:
收稿日期:2012-07-28 修回日期:2014-04-17
基金项目:国家自然科学基金(21075138); 环境模拟与污染控制国家重点联合实验室开放基金(13K02ESPCT); 徐州市科技局计划项目(XM13B111)
作者简介:李鸣建(1957-),女,副教授,主要研究方向:物质构效关系,E-mail:lmj@xzit.edu.cn; 通讯作者:冯长君(1954-),教授,主要研究方向:物质构效学,E-mail:fengcjxznu@xznu.edu.cn。
引文格式:李鸣建,陈艳,冯长君.马来酸酯类化合物结构与抑菌活性密度泛函理论研究[J].南京理工大学学报,2014,38(5):695-700.
投稿网址:http://zrxuebao.njust.edu.cn
更新日期/Last Update: 2014-10-31