A new quantitative structure-property relationship model to predict bioconcentration factors of polychlorinated biphenyls (PCBs) in fishes using E-state index and topological descriptors

被引:26
作者
de Melo, Eduardo Borges [1 ]
机构
[1] Western Parana State Univ Unioeste, Theoret Med & Environm Chem Lab LQMAT, Dept Pharm, BR-85819110 Cascavel, Parana, Brazil
关键词
QSPR; Polychlorinated biphenyls; Bioconcentration factor; PLS; OPS; OECD principles; QSAR MODELS; FACTOR BCF; VALIDATION; QSPR; CHEMISTRY; SELECTION; DIOXINS; SYSTEM;
D O I
10.1016/j.ecoenv.2011.08.026
中图分类号
X [环境科学、安全科学];
学科分类号
08 ; 0830 ;
摘要
A quantitative structure-property relationship (QSPR) study for predicting the logarithm of bioconcentration factors (Log BCF) of polychlorinated biphenyls (PCBs) is presented in this work. For this, the descriptors were obtained using only the Simplified Molecular Input Line Entry System (SMILES) strings in the free web server Parameter Client. The model was built using the Partial Least Squares (PLS) regression method. The best model presented five descriptors (one E-state index and four topological descriptors) and a high quality for fit, internal, and external predictions. The leave-N-out (LNO) cross validation and the y-randomization test showed the model is robust and has no shown chance correlation. With a second test set, the model was compared to other models and presented a root mean square error (RMSE) very close to the best model. The mechanistic interpretation was corroborated by other works in the literature and by the descriptors' theory. Thus, the results meet the five Organization for Economic Co-operation and Development (OECD) principles for validation of QSA(P)R models, and it is expected the model can effectively predict the BCF values in fishes of the PCB congeners without highly reliable experimental BCF. (C) 2011 Elsevier Inc. All rights reserved.
引用
收藏
页码:213 / 222
页数:10
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