化工进展 ›› 2016, Vol. 35 ›› Issue (03): 879-883.DOI: 10.16085/j.issn.1000-6613.2016.03.035

• 精细化工 • 上一篇    下一篇

反丁烯二酸酯类物质结构与抑菌性能关系

邱松山, 姜翠翠, 周如金, 刘杰凤   

  1. 广东石油化工学院果蔬加工与贮藏工程中心, 广东 茂名 525000
  • 收稿日期:2015-06-17 修回日期:2015-09-01 出版日期:2016-03-05 发布日期:2016-03-05
  • 通讯作者: 周如金,博士,教授。E-mail:tustqss@163.com.
  • 作者简介:邱松山(1978-),男,博士,副教授
  • 基金资助:

    广东省部产学研结合项目(2013B090600032)、茂名市科技计划(2014007)及果蔬加工与贮藏工程中心开放基金(2015A005)项目

Relationship between antibacterial activity and structure of fumaric acid esters

QIU Songshan, JIANG Cuicui, ZHOU Rujin, LIU Jiefeng   

  1. Development Centre of Technology for Fruit & Vegetables Storage and Processing Engineering, Guangdong University of Petrochemical Technology, Maoming 525000, Guangdong, China
  • Received:2015-06-17 Revised:2015-09-01 Online:2016-03-05 Published:2016-03-05

摘要: 采用密度泛函理论(DFT)考察反丁烯二酸酯类化合物结构与抑菌活性之间的定量构效关系(QSAR).在B3LYP/6-311++ G(d)基组下对13种反丁烯二酸酯类化合物进行几何构型优化和频率计算,选取最高占据轨道能量EHOMO、最低空轨道能量ELUMO及两者的绝对差值DE、偶极矩(μ)、零点能、平均分子极化率(p)等量化参数作为量子化学描述符,通过多元逐步回归分析筛选影响抑菌活性的主要因素并建立化合物量化参数和抑菌活性之间的QSAR模型方程,并用留一法交叉验证模型的稳定性及预测能力。结果表明反丁烯二酸酯类化合物抑制枯草芽孢杆菌性能与其结构参数DEμ、ZPE之间存在着较高的线性关系,DEμ越大,抑菌活性越大,相关系数R=0.957,此类化合物抑制枯草芽孢杆菌活性的理论值与实验值的相关性良好,表明该模型能较好的预测此类具有α,β-不饱和羰基母体结构的反丁烯二酸酯类化合物的抑菌活性。

关键词: 反丁烯二酸酯类化合物, 构效关系, 抗菌活性, 计算机模拟, 构型优化, 外部预测

Abstract: The quantitative structure-activity relationship (QSAR) between molecular structures and antibacterial activity of fumaric acid esters was studied using the density functional theory (DFT) at the B3LYP functional at the level of 6-311++G(d) basis set. The energy of the highest occupied molecular orbital EHOMO,the energy of the lowest unoccupied molecular orbital ELUMO,the difference of energy DE,the dipole moment μ,the zero-point energy (ZPE) and the average molecular polarizability (p) were selected as the structural descriptors. The geometries and the QSAR model of the samples were optimized and the stable complexes were obtained. The stability and predictive ability of the model were examined by the “leave-one-out” cross-validation method.The results suggest that the dipole moment μ,DE and zero-point energy are the predominant factors affecting the antibacterial activity against B. subtilis. The antifungal activity increases with the increase of DE and μ. The obtained QSAR model has a good stability and predictive ability for such inhibitors.

Key words: fumaric acid esters, structure-activity relationship, antibacterial activity, computer simulation, structure optimization, outer prediction

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