有机污染物的被动采样材料-水分配系数的QSAR研究QSAR Models for Predicting Partition Coefficients of Organic Pollutants between Passive Sampling Materials and Water
杨蕾;罗翔;王雅;张亚南;陈景文;
摘要(Abstract):
污染物的被动采样材料-水分配系数(K_(PW))是衡量被动采样器性能和进行优化的一个重要指标,由于实验方法难以逐个测定众多污染物的K_(PW)值,有必要发展其KP W预测方法。本研究选取聚乙烯(PE)、聚丙烯酸酯(PA)和硅橡胶(SR)3类常用的被动采样材料共7种,采用多元线性回归分析方法构建可用于K_(PW)预测的定量构效关系(QSAR)模型。所构建的QSAR模型具有良好的拟合优度(R2a dj介于0.806~0.989)、稳健性(Q2L O O和Q2B O O T分别介于0.786~0.988和0.773~0.801)和预测能力(R_(ext)~2和Q_(ext)~2分别介于0.769~0.989和0.757~0.982),可以用于预测烷烃、烯烃、芳香类、醇类、酮类、酯类、醚类等多种有机污染物的log KP W值。有机污染物的log KP W与分子Mc Gowan体积(Vx)、氯原子个数(n Cl)、环周长(Rperim)、多重键个数(n BM)、N,O极性贡献的拓扑极性表面积(TPSA(NO))、[-N(=)=]结构个数(Ndds N)和羟基个数(nROH)等参数有关。
关键词(KeyWords): 被动采样材料-水分配系数;聚乙烯;聚丙烯酸酯;硅橡胶;定量构效关系
基金项目(Foundation): 国家自然科学基金(21325729;21661142001)
作者(Author): 杨蕾;罗翔;王雅;张亚南;陈景文;
Email:
DOI:
参考文献(References):
- [1]Booij K,van Bommel R,van Aken H M,et al.Passive sampling of nonpolar contaminants at three deep-ocean sites[J].Environmental Pollution,2014,195:101-108
- [2]Sacks V P,Lohmann R.Development and use of polyethylene passive samplers to detect triclosans and alkylphenols in an urban estuary[J].Environmental Science&Technology,2011,45(6):2270-2277
- [3]Chen C E,Zhang H,Ying G G,et al.Evidence and recommendations to support the use of a novel passive water sampler to quantify antibiotics in wastewaters[J].Environmental Science&Technology,2013,47(23):13587-13593
- [4]Alvarez D A,Cranor W L,Perkins S D,et al.Chemical and toxicologic assessment of organic contaminants in surface water using passive samplers[J].Journal of Environmental Quality,2008,37(3):1024-1033
- [5]Endo S,Droge S T J,Goss K U.Polyparameter linear free energy models for polyacrylate fiber-water partition coefficients to evaluate the efficiency of solid-phase microextraction[J].Analytical Chemistry,2011,83(4):1394-1400
- [6]Choi Y,Cho Y M,Luthy R G.Polyethylene-water partitioning coefficients for parent-and alkylated-polycyclic aromatic hydrocarbons and polychlorinated biphenyls[J].Environmental Science&Technology,2013,47(13):6943-6950
- [7]陈景文,全燮.环境化学[M].大连:大连理工大学出版社,2009:260Chen J W,Quan X.Environmental Chemistry[M].Dalian:Dalian University of Technology P ress,2009:260(in Chinese)
- [8]Lohmann R.Critical review of low-density polyethylene’s partitioning and diffusion coefficients for trace organic contaminants and implications for its use as a passive sampler[J].Environmental Science&Technology,2011,46(2):606-618
- [9]Hale S E,Martin T J,Goss K U,et al.Partitioning of organochlorine pesticides from water to polyethylene passive samplers[J].Environmental P ollution,2010,158(7):2511-2517
- [10]Josefsson S,Arp H P H,Kleja D B,et al.Determination of polyoxymethylene(P OM)-water partition coefficients for oxy-P AHs and P AHs[J].Chemosphere,2015,119:1268-1274
- [11]Perron M M,Burgess R M,Suuberg E M,et al.Performance of passive samplers for monitoring estuarine water column concentrations:1.Contaminants of concern[J].Environmental Toxicology and Chemistry,2013,32(10):2182-2189
- [12]Reitsma P J,Adelman D,Lohmann R.Challenges of using polyethylene passive samplers to determine dissolved concentrations of parent and alkylated P AHs under cold and saline conditions[J].Environmental Science&Technology,2013,47(18):10429-10437
- [13]Sacks V P,Lohmann R.Freely dissolved PBDEs in water and porewater of an urban estuary[J].Environmental P ollution,2012,162:287-293
- [14]Kwon J H,Wuethrich T,Mayer P,et al.Dynamic permeation method to determine partition coefficients of highly hydrophobic chemicals between poly(dimethylsiloxane)and water[J].Analytical Chemistry,2007,79(17):6816-6822
- [15]Booij K,Smedes F,van Weerlee E M,et al.Environmental monitoring of hydrophobic organic contaminants:The case of mussels versus semipermeable membrane devices[J].Environmental Science&Technology,2006,40(12):3893-3900
- [16]Hawthorne S B,Miller D J,Grabanski C B.Measuring low picogram per liter concentrations of freely dissolved polychlorinated biphenyls in sediment pore water using passive sampling with polyoxymethylene[J].Analytical Chemistry,2009,81(22):9472-9480
- [17]OECD.Guidance document on the validation of(Quantitative)Structure-Activity Relationships[(Q)SAR]models[R].P aris:OECD,2007
- [18]Booij K,Hofmans H E,Fischer C V,et al.Temperature-dependent uptake rates of nonpolar organic compounds by semipermeable membrane devices and lowdensity polyethylene membranes[J].Environmental Science&Technology,2003,37(2):361-366
- [19]Adams R G,Lohmann R,Fernandez L A,et al.Polyethylene devices:P assive samplers for measuring dissolved hydrophobic organic compounds in aquatic environments[J].Environmental Science&Technology,2007,41(4):1317-1323
- [20]Paschke A,Popp P.Solid-phase microextraction fibrewater distribution constants of more hydrophobic organic compounds and their correlations with octanol-water partition coefficients[J].Journal of Chromatography A,2003,999(1):35-42
- [21]Yates K,Davies I,Webster L,et al.Passive sampling:P artition coefficients for a silicone rubber reference phase[J].Journal of Environmental Monitoring,2007,9(10):1116-1121
- [22]Smedes F,Geertsma R W,Zande T,et al.Polymer-water partition coefficients of hydrophobic compounds for passive sampling:Application of cosolvent models for validation[J].Environmental Science&Technology,2009,43(18):7047-7054
- [23]Thompson J M,Hsieh C H,Luthy R G.Modeling uptake of hydrophobic organic contaminants into polyethylene passive samplers[J].Environmental Science&Technology,2015,49(4):2270-2277
- [24]Hale S E,Tomaszewski J E,Luthy R G,et al.Sorption of dichlorodiphenyltrichloroethane(DDT)and its metabolites by activated carbon in clean water and sediment slurries[J].Water Research,2009,43(17):4336-4346
- [25]Cornelissen G,Pettersen A,Broman D,et al.Field testing of equilibrium passive samplers to determine freely dissolved native polycyclic aromatic hydrocarbon concentrations[J].Environmental Toxicology and Chemistry,2008,27(3):499-508
- [26]Fernandez L A,Mac Farlane J K,Tcaciuc A P,et al.Measurement of freely dissolved P AH concentrations in sediment beds using passive sampling with low-density polyethylene strips[J].Environmental Science&Technology,2009,43(5):1430-1436
- [27]Bao L J,You J,Zeng E Y.Sorption of PBDE in lowdensity polyethylene film:Implications for bioavailability of BDE-209[J].Environmental Toxicology and Chemistry,2011,30(8):1731-1738
- [28]Jhin C,Hwang K T.Prediction of radical scavenging activities of anthocyanins applying adaptive neuro-fuzzy inference system(ANFIS)with quantum chemical descriptors[J].International Journal of Molecular Sciences,2014,15(8):14715-14727
- [29]Noru2is M J.SPSS Inc.SPSS 7.5 Guide to Data Analysis[M].Upper Saddle River,New Jersey:Prentice Hall,1997:458
- [30]Gramatica P.Principles of QSAR models validation:Internal and external[J].QSAR&Combinatorial Science,2007,26(5):694-701
- [31]Vitha M,Carr P W.The chemical interpretation and practice of linear solvation energy relationships in chromatography[J].Journal of Chromatography A,2006,1126(1):143-194
- [32]Li F,Xie Q,Li X H,et al.Hormone activity of hydroxylated polybrominated diphenyl ethers on human thyroid receptor-β:In vitro and in silico investigations[J].Environmental Health Perspectives,2010,118(5):602-606
- [33]Schüürmann G,Ebert R U,Kühne R.Prediction of the sorption of organic compounds into soil organic matter from molecular structure[J].Environmental Science&Technology,2006,40(22):7005-7011
- [34]Fernández A,Rallo R,Giralt F.Prioritization of in silico models and molecular descriptors for the assessment of ready biodegradability[J].Environmental Research,2015,142:161-168
- [35]Abraham M H,Mc Gowan J C.The use of characteristic volumes to measure cavity terms in reversed phase liquid chromatography[J].Chromatographia,1987,23(4):243-246
- [36]Wang Y,Chen J W,Yang X H,et al.In silico model for predicting soil organic carbon normalized sorption coefficient(KO C)of organic chemicals[J].Chemosphere,2015,119:438-444
- [37]Tang W Z,Wang F.Quantitative structure activity relationship(QSAR)of chlorine effects on ELU M Oof disinfection by-product:Chlorinated alkanes[J].Chemosphere,2010,78(7):914-921
- [38]Edraki N,Hemmateenejad B,Miri R,et al.QSARstudy of phenoxypyrimidine derivatives as potent inhibitors of p38 kinase using different chemometric tools[J].Chemical Biology&Drug Design,2007,70(6):530-539
- [39]Butina D.Performance of Kier-hall E-state descriptors in quantitative structure activity relationship(QSAR)studies of multifunctional molecules[J].Molecules,2004,9(12):1004-1009
- [40]Patel J R,Prajapati L M.Predictive QSAR modeling on tetrahydropyrimidine-2-one derivatives as HIV-1 protease enzyme inhibitors[J].Medicinal Chemistry Research,2013,22(6):2795-2801