取代酚对日本长腿蛙蝌蚪急性毒性的QSAR研究  

QSAR study of substituted phenol compounds'acute toxicities to rana japonica todpoles

作　　者：彭艳芬[1] 刘天宝[1] 严永新[1] 汪新[1] 

机构地区：[1]池州学院,化学材料与工程实验中心,安徽池州247000

出　　处：《计算机与应用化学》2010年第11期1518-1522,共5页Computers and Applied Chemistry

基　　金：安徽省自然科学基金项目(090414190);安徽省高等学校省级优秀青年人才基金项目(2010SQRL133);安徽省教育厅自然科学基金项目(KJ2009A122,KJ2010B135)

摘　　要：用Hartree-Fock(HF)和DFT-B3LYP方法,分别在较高基组6-31G**和6-311G**水平下,全优化计算了21种取代酚化合物。从中获得分子最高占用和最低空轨道能(EHOMO和ELUMO)、前线轨道能级差(ΔE=EHOMO-ELUMO)、分子总能量(ET)、氢原子所带的最高正电荷(QH+)、最负原子的静电荷(Q-)、分子偶极矩(μ)和分子体积(V)等描述符。结合文献中标题化合物对日本长腿蛙蝌蚪的毒性值(-logLC50)和辛醇/水分配系数(logKOW),由线性回归方法成功建立包含logKOW、ELUMO和Q-的三参数QSAR模型。其中,模型(5)的复相关系数R2=0.9448,交叉验证系数Q2=0.9205,标准偏差SE=0.187,Fisher检验值F=98.390,故其预测能力较好。由此推断,标题物对日本长腿蛙蝌蚪的毒性作用分为2步,首先穿过细胞壁在细胞内富集,以logKOW和Q-描述;其次与亲核试剂发生亲电反应,以ELUMO表示。Structural parameters of 21 substituted phenols were computed at four levels using Hartree-Fock（HF）and DFT methods.EHOMO,ELUMO,ΔE,ET,QH^＋,Q^-,μand V were selected as structural descriptors.The acute toxicity（-logLC50）of these compounds to Rana Japonica todpoles along with hydrophobicity described by logKOW,the above eight structural parameters,was used to established the quantitative structure-activity relationships（QSAR）by multiple linear regression.Then,four models established by logKOW,ELUMO and Q-were obtained.The R^2,Q^2,SE and F for model（5） established in this study were 0.9448,0.9205,0.187 and 98.390,respectively.The result indicated that the model had good predictability.In light of the model,the toxic actions of phenols included two steps：one was the collection of the compounds in vivo,which were described by logKOW and Q-;the next was the electronic reactions between the chemicals and macromolecular compounds,which was represented by ELUMO.

关 键 词：取代酚 日本长腿蛙蝌蚪 密度泛函理论 定量构效关系 

分 类 号：O641[理学—物理化学] TQ015.9[理学—化学]