根据分子连接性指数和基团校正因子预测有机化合物在鱼体中的生物富集因子

应用生态学报 ›› 2000, Vol. ›› Issue (2): 277-282.

根据分子连接性指数和基团校正因子预测有机化合物在鱼体中的生物富集因子

卢晓霞, 陶澍, 胡海瑛

北京大学城市与环境学系, 北京100871

收稿日期:1998-11-08 修回日期:1999-05-04 出版日期:2000-03-25
通讯作者: 陶澍
基金资助:
国家自然科学基金重点项目(49632060);国家杰出青年基金资助项目(49525102)

Prediction of bioconcentration factors of organic compounds in fish by molecular connectivity indices and function correction factors

LU Xiaoxia, TAO Shu, HU Haiying

Department of Urban and Environmental Sciences, Peking University, Beijing 100871

Received:1998-11-08 Revised:1999-05-04 Online:2000-03-25

摘要/Abstract

摘要： 研究了239种有机化合物的BCF预测模型,结果显示仅根据分子连接性指数 (MCI)的线性模型不能准确计算极性化合物的BCF,也不适用于超疏水性化合物.在模型中引入基团校正因子后,极性化合物的计算误差明显降低.对数据进行曲线拟合,所得模型的估算精度进一步提高.最终确定以 (⁰χ^v) 2 、(²χ^v)^1/2、²χ、³χ_c、⁰χ^v及OH、NH₂ 、NO₂ 、NCOO等 10个基团校正因子为参数建立预测模型,并对研究化合物logBCF计算值与实测值的差异及原因进行了分析.运用Jackknifed法按随机分组和化合物分类两种方式,对预测模型的稳健性进行了检验.

关键词: 有机化合物, 生物富集因子, 分子连接性指数, 基团校正因子

Abstract: Studies on the prediction models of bioconcentration factors(BCF) of 239 organic compounds showed that the BCFs of polar organic compounds could not be accurately predicted solely by the linear model based on molecular connectivity indices.Additionally,the linear model was not suitable for superphilic compounds.By introducing function correction factors to the model,the residual of the prediction model for polar organic compounds was reduced significantly.When the nonlinear estimation was used,the accuracy of the obtained model was further improved.The final prediction model consisted of parameters (⁰χ^v)²,(²χ^v) ^1/2, ²χ,³χ_c, ⁰χ^v and 10 correction factors for function groups OH,NH₂,NO₂,NCOO,etc.The difference between calculated and observed values of logBCF and its causes were analyzed.The robustness of the model was tested by Jackknifed method,based on random grouping and compound classification.

Key words: Organic compounds, Bioconcentration factor, Molecular connectivity indices, Function correction factors

卢晓霞, 陶澍, 胡海瑛. 根据分子连接性指数和基团校正因子预测有机化合物在鱼体中的生物富集因子[J]. 应用生态学报, 2000, (2): 277-282.

LU Xiaoxia, TAO Shu, HU Haiying. Prediction of bioconcentration factors of organic compounds in fish by molecular connectivity indices and function correction factors[J]. Chinese Journal of Applied Ecology, 2000, (2): 277-282.

参考文献

1 Barron MG.1990.Bioconcentration.Environ Sci Technol,24(11):1612～1618
2 Devillers J,Bintein S and Domine D.1996.Comparison of BCF models based on logP.Chemosphere,33(6):1047～1065
3 Dietrich SW,Dreyer ND and Hansch C.1980.Confidence interval estimators for parameters associated with quantitative structure-activity relationships.J Med　Chem,23:1201～1205
4 Donald M.1982.Correlation of bioconcentration factors.Environ　Sci　Technol,16(2):274～278
5 Freitag D,Ballhorn L,and Geyer H.1985.Environmental hazard profile of organic chemicals: An experimental method for the assessment of the behaviour of organic chemicals in the ecosphere by means of simple laboratory tests with 14C Labelled Chemicals.Chemosphere,14(10):1589～1616
6 Gobas FAPC,Clark KE,and Shiu WY et al.1989.Bioconcentration of polybrominated benzenes and biphenyls and related superhydrophobic chemicals in fish: Role of bioavailability and elimination into the feces.Environ　Toxicol　Chem,8:231～245
7 Gobas FAPC.1990.Bioaccumulation of some polychlorinated dibenzo-p-dioxins and octachloro-dibenzofuran in the guppy,Poecilia reticulata.Chemosphere,20(5):495～512
8 Isnard P and Lambert S.1988.Estimating bioconcentration factors from octanol-water partition coefficient and aqueous solubility.Chemosphere,17(1):21～34
9 Kier LB and Hall LH.1986.Molecular Connectivity in Struture-Activity Analysis.Research Studies Press.England.10～20
10 Koch R.1983.Molecular connectivity index for assessing ecotoxicological behaviour of organic compounds.Toxicol Environ Chem,6:87～96
11 Lu X-X(卢晓霞),Tao S(陶　澍).1999.Prediction of bioconcentration factors of organic compounds in fish by molecular connectivity indices and function correction factors.Chin Environ Sci(环境科学),20:9～12(in Chinese)
12 Lyman WJ,Reehl WF,eds.1991.Trans.Xu Zh-H(许志宏).1991.Environmental characters of organic chemicals.In: Handbook of chemical properties estimation.Beijing: Chemical Engineering Press.169～195(in Chinese)
13 Mackay D,Shiu WY and Ma KC eds.1992.Illustrated Handbook of Physical-Chemical Properties and Environmental Fate for Organic Chemicals.Michigan:Lewis Publishers
14 Nendza M.1993.QSAR of bioconcentration: validity assessment of logPow/logBCF correlations.In: Nagel R and Loskill R eds.Bioaccumulation in Aquatic Systems.VCH,Weinheim.43～66
15 Oliver BG and Niimi AJ.1983.Bioconcentration of chlorobenzenes from water by rainbow trout: correlations with partition coefficients and environmental residues.Environ　Sci　Technol,17(5):287～291
16 Oliver BG and Niimi AJ.1984.Rainbow trout bioconcentration of some halogenated aromatics from water at environmental concentrations.Environ Toxicol Chem,3:271～277
17 Oliver BG and Niimi AJ.1985.Bioconcentration factors of some halogenated organics for rainbow trout: limitations in their use for prediction of environmental residues.Environ Sci Technol,19(9):842～849
18 Opperhuizen A,van der Velde EW and Gobas FAPC et al.1985.Relationship between bioconcentration in fish and steric factors of hydrophobic chemicals.Chemosphere,14(11/12):1871～1896
19 Sabljic A and Protic M.1982.Molecular connectivity: A novel method for prediction of bioconcentration factor of hazardous chemicals.Chem　Biol　Interaction,42:301～310
20 Sabljic A 1987.The prediction of fish bioconcentration factors of organic pollutants from the molecular connectivity model.Z.gesamte Hyg,33:493～496
21 Smith AD,Bharath A and Mallard D et al.1990.Bioconcentration kinetics of some chlorinated benzenes and chlorinated phenols in American flagfish,Jordanella floridae.Chemosphere,20(3/4):379～386
22 Tsuda T,Kojima M and Harada H et al.1997.Relationships of bioconcetration factors of organophosphate pesticides among species of fish.Comp Biochem Physiol,116C(3):213～218
23 Veith GD,Macek KJ,Petrocelli SR et al.1980.An evaluation of using partition coefficients and water solubility to estimate bioconcentration factors for organic chemicals in fish.In: Eaton JG,Parrish PR and Hendricks AC eds.Aquatic Toxicology.ASTM STP 707.pp.116～129
24 Voogt P de,Muir DCG and Webster GRB et al.1990.Quantitative structure-activity relationships for the bioconcentration in fish of seven polychlorinated dibenzodioxins.Chemosphere,21(12):1385～1396
25 Watze de Wolf,Eddy SEY and Willem S et al.1994.Bioconcentration kinetics of chlorinated anilines in guppy,Poecilia reticulata.Chemosphere,28(1):159～167

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