物理化学学报 >> 2005, Vol. 21 >> Issue (03): 267-272.doi: 10.3866/PKU.WHXB20050308

研究论文 上一篇    下一篇

多氯联苯的定量结构－性质(活性)关系

邹建卫; 蒋勇军; 胡桂香; 曾敏; 庄树林; 俞庆森   

  1. 浙江大学宁波理工学院分子设计与营养工程市重点实验室,宁波　315104
  • 收稿日期:2004-07-21 修回日期:2004-10-08 发布日期:2005-03-15
  • 通讯作者: 邹建卫 E-mail:jwzou@css.zju.edu.cn

QSPR/QSAR Studies on the Physicochemical Properties and Biological Activities of Polychlorinated Biphenyls

ZOU Jian-Wei; JIANG Yong-Jun; HU Gui-Xiang; ZENG Min; ZHUANG Shu-Lin; YU Qing-Sen   

  1. Key Laboratory for Molecular Design and Nutrition Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo　315104
  • Received:2004-07-21 Revised:2004-10-08 Published:2005-03-15
  • Contact: ZOU Jian-Wei E-mail:jwzou@css.zju.edu.cn

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摘要：

多氯联苯(PCBs)是一类重要的持久性环境污染物.首先对所有209个PCB分子进行了HF/6-31G*水平上的结构优化, 在优化结构上获得了分子的表面静电势分布, 并在此基础上对其统计导出的参数进行了计算．其后, 运用多元线性回归方法对PCBs的水溶性、正辛醇/水分配系数、正辛醇/空气分配系数、土壤吸附性、水溶液活度系数、298 K超冷流体蒸汽压、总分子表面积、色谱保留指数、升华焓、蒸发焓、熔融焓、PCB结合芳烃受体活性数据、生物降解度以及生物降解速率参数等理化性质和生物活性与分子的结构参数进行了关联．结果表明:分子静电势参数结合分子表面积和常规的量子化学参数可以很好地用于表达多氯联苯分子理化性质和生物活性与其分子结构间的定量关系．

关键词: 定量结构－性质关系, 定量结构－活性关系, 分子静电势, 从头算, 多氯联苯

Abstract:

Polychlorinated biphenyls(PCBs), an important kind of toxic pollutant, are persistent in the environment and accumulative in many species. Ab initio calculations have been performed for all 209 PCB congeners at the HF/6-31G* level. Electrostatic potentials and subsequently derived statistically based structural descriptors have been obtained. Linear relationships between aqueous solubility(lgSW), n-octanol/water partition coefficient (lgKOW),n-octanol/air partition coefficient (lgKOA), soil sorption (lgKOC), aqueous activity coefficient(lgYW), 298 K supercooled liquid vapour pressures(lgpL), total molecular surface area (TSA), gas-chromatographic relative retention time (RRT), enthalpy of sublimation (ΔHsubl), enthalpy of vaporization (ΔHvap), enthalpy of fusion (ΔHfus), Aryl hydrocarbon receptor biding affinity (pEC50),biodegradability (Biodeg％) and Microbial elimination rate constant(－lgk) of PCBs and theoretical descriptors have been established by multiple regression method. It appears that the quantities derived from electrostatic potentials, Vmin, Vs,min, Vs,max, Vs, Π,σ2tot,ΣVs+,>,ΣVs-, together with the molecular surface area and some popular quantum chemical descriptors (e.g. EHOMO and ELUMO) can be well used to express the quantitative structure-property (activity) relationships of PCBs. Although the correlation equations for some physicochemical properties and biological activities are not superior to those previously established with other types of structural parameters, the parameter set used in the present systematic quantitative structure-property relationship (QSPR)/quantitative structure-activity relationship (QSAR) study was proven to have more general applicability.

Key words: QSPR, QSAR, Molecular electrostatic potential, Ab initio;　Polychlorinated biphenyl