Prediction of Toxicity of Phenols and Anilines to Algae by Quantitative Structure-activity Relationship  

作　　者：GUANG-HUA LU CHAO WANG XIAO-LING GUO 

机构地区：[1]State Key Laboratory for Hydrology-water Resources and Hydraulic Engineering, College of Environmental Science and Engineering, Hohai University, Nanjing 210098, Jiangsu, China

出　　处：《Biomedical and Environmental Sciences》2008年第3期193-196,共4页生物医学与环境科学（英文版）

基　　金：This work was supported by the Program for New Century Excellent Talents in University (No. 05-0481);National "973" Great Foundation Research Items of China (No. 2002CB412303)

摘　　要：Objective To measure the toxicity of phenol, aniline, and their derivatives to algae and to assess, model, and predict the toxicity using quantitative structure-activity relationship （QSAR） method. Methods Oxygen production was used as the response endpoint for assessing the toxic effects of chemicals on algal photosynthesis. The energy of the lowest unoccupied molecular orbital （ELUMO） and the energy of the highest occupied molecular orbital （EHOMO） were obtained from the ChemOffice 2004 program using the quantum chemical method MOPAC, and the frontier orbital energy gap （△E） was obtained. Results The compounds exhibited a reasonably wide range of algal toxicity. The most toxic compound was α-naphthol, whereas the least toxic one was aniline. A two-descriptor model was derived from the algal toxicity and structural parameters： logl/EC50=0.2681ogKow-1.006△E＋11.769 （n=20, r^2=0.946）. This model was stable and satisfactory for predicting toxicity. Conclusion Phenol, aniline, and their derivatives are polar narcotics. Their toxicity is greater than estimated by hydrophobicity only, and addition of the frontier orbital energy gap AE can significantly improve the prediction of logKow-dependent models.Objective To measure the toxicity of phenol, aniline, and their derivatives to algae and to assess, model, and predict the toxicity using quantitative structure-activity relationship （QSAR） method. Methods Oxygen production was used as the response endpoint for assessing the toxic effects of chemicals on algal photosynthesis. The energy of the lowest unoccupied molecular orbital （ELUMO） and the energy of the highest occupied molecular orbital （EHOMO） were obtained from the ChemOffice 2004 program using the quantum chemical method MOPAC, and the frontier orbital energy gap （△E） was obtained. Results The compounds exhibited a reasonably wide range of algal toxicity. The most toxic compound was α-naphthol, whereas the least toxic one was aniline. A two-descriptor model was derived from the algal toxicity and structural parameters： logl/EC50=0.2681ogKow-1.006△E＋11.769 （n=20, r^2=0.946）. This model was stable and satisfactory for predicting toxicity. Conclusion Phenol, aniline, and their derivatives are polar narcotics. Their toxicity is greater than estimated by hydrophobicity only, and addition of the frontier orbital energy gap AE can significantly improve the prediction of logKow-dependent models.

关 键 词：TOXICITY QSARS Frontier orbital energy gap PREDICTION 

分 类 号：Q949.2[生物学—植物学]