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

GUANG-HUA LU; CHAO WANG; XIAO-LING GUO

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Volume 21 Issue 3

Jun. 2008

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Article Navigation > Biomedical and Environmental Sciences > 2008 > 21(3): 193-196

GUANG-HUA LU, CHAO WANG, XIAO-LING GUO. Prediction of Toxicity of Phenols and Anilines to Algae by Quantitative Structure-activity Relationship[J]. Biomedical and Environmental Sciences, 2008, 21(3): 193-196.

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GUANG-HUA LU, CHAO WANG, XIAO-LING GUO. Prediction of Toxicity of Phenols and Anilines to Algae by Quantitative Structure-activity Relationship[J]. Biomedical and Environmental Sciences, 2008, 21(3): 193-196.

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

State Key Laboratory for Hydrology-water Resources and Hydraulic Engineering, College of Environmental Science and Engineering, Hohai University, Nanjing 210098, Jiangsu, China

Funds: 教育部新世纪优秀人才支持计划(05-0481)%国家重点基础研究发展计划(973计划)(2002CB412303)

Abstract

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 (E<,HOMO>) Were obtained from the ChemOffice 2004 program using the quantum chemical method MOPAC, and the frontier orbital energy gap (ΔE) 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=0.268logKow-1.006ΔE+11.769 (n=20,r2=0.946). This model was stable and satisfactory for predicting toxicity. Conclusion Phenol aniline, and their derivatives axe polar narcotics. Their toxicity is greater than estimated by hydrophobicity only, and addition of the frontier orbital energy gap ΔE can significantly improve the prediction of logKow-dependont models.
- Toxicity,
- QSARs,
- Frontier orbital energy gap,
- Prediction
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

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

State Key Laboratory for Hydrology-water Resources and Hydraulic Engineering, College of Environmental Science and Engineering, Hohai University, Nanjing 210098, Jiangsu, China

Funds: 教育部新世纪优秀人才支持计划(05-0481)%国家重点基础研究发展计划(973计划)(2002CB412303)

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Abstract: 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 (E<,HOMO>) Were obtained from the ChemOffice 2004 program using the quantum chemical method MOPAC, and the frontier orbital energy gap (ΔE) 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=0.268logKow-1.006ΔE+11.769 (n=20,r2=0.946). This model was stable and satisfactory for predicting toxicity. Conclusion Phenol aniline, and their derivatives axe polar narcotics. Their toxicity is greater than estimated by hydrophobicity only, and addition of the frontier orbital energy gap ΔE can significantly improve the prediction of logKow-dependont models.

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