氰戊菊酯手性拆分及其对扁藻胁迫作用的研究
|
摘要
本研究使用微乳电动毛细管色谱技术建立了一种针对氰戊菊酯对映异构体进行手性拆分的快捷方法。通过探讨氰戊菊酯及其高效体(S,S-氰戊菊酯)对扁藻的胁迫作用,了解到氰戊菊酯对映异构体的拆分可以减少其对环境的施放量,这对保障生物食物链及食品的安全性具有指导意义。
本实验使用微乳电动毛细管色谱方法,采用β-环糊精作为手性选择剂,成功地进行了氰戊菊酯对映异构体的手性拆分。通过优化实验条件如缓冲溶液的组成、浓度、pH,微乳的组成及浓度,环糊精浓度等,得到最佳拆分参数:选用57cm(有效长度50cm)×75μm(内径)的石英毛细管,分离温度为25℃,分离电压为15KV,β-环糊精的浓度为30mmol/L,缓冲溶液pH=6.5(5mmol/L磷酸二氢钠+10mmol/L硼砂溶液),以140mmol/L十二烷基硫酸钠+30mmol/L正庚烷+300mmol/L正丁醇为微乳。在此条件下可使氰戊菊酯的4个对映体基线分离,并通过内标法确定出S,S-氰戊菊酯的峰型归属。
本实验还考察了氰戊菊酯及S,S-氰戊菊酯对扁藻的96h急性毒性实验。结果显示:氰戊菊酯和S,S-氰戊菊酯对扁藻的生长情况,表现为低浓度刺激,高浓度抑制。氰戊菊酯的96hEC_(50)为39.2mg/L,S,S-氰戊菊酯96hEC_(50)为5.9mg/L。两者相差6.6倍,后者对扁藻的毒性作用大于前者。进而测定了在不同浓度氰戊菊酯和S,S-氰戊菊酯胁迫作用下扁藻的各生理指标(叶绿素a,可溶性蛋白质,超氧化物歧化酶(SOD),过氧化物酶(POD)),其中SOD在胁迫前后的下降率最大,说明氰戊菊酯和S,S-氰戊菊酯对扁藻的胁迫作用主要表现在对酶的抑制作用。
This work has developed a quick method for chiral separation of fenvalerate enantiomers using Microemulsion Electrokinetic Chromatography(MEEKC).By investigating the stress effects of fenvalerate and its enantiomer s,s-fenvalerate on Platymonas subcordiformis,it is known that the chiral separation of fenvalerate enantiomers can reduce the emitted amounts of fenvalerate into the environment and is also valuable for the protection of food chain and the food safety.
Four fenvalerate enantiomers were resolved in the baseline separation by MEEKC usingβ-cyclodextrin as a chiral selector.The electrophoretic experiment parameters such as the buffer components,buffer concentration and pH,the components and concentration of microemulsion,and the concentration ofβ-cyclodextrin were optimized.An uncoated fused-silica capillary of 75μm i.d and length of 57cm(effective 50cm) was used.The capillary temperature was maintained at 25℃,and the sample was separated at 15KV.The optimal separation conditions were achieved with a background electrolyte of 5mmol/L NaH_2PO_4+10mmol/L borax (pH6.5),and the microemulsion of 140mmol/LSDS+30mmol/L n-heptane+300 mmol/L.1-butanol.Further,the peaks of s,s-fenvalerate was confirmed by internal standard method in this electrophoresis conditions.
This work also evaluated 96 hours acute toxicity of fenvalerate and s,s-fenvalerate for Platymonas subcordiformis.According to the experimental results, the 96hEC_(50) of fenvalerate was 39.2mg/L and the 96hEC_(50) of s,s-fenvalerate was 5.9mg/L.The former was 6.6 times high than the latter.The toxicity of s,s-fenvalerate was greater than fenvalerate.The physiological indexes of Platymonas subcordiformis such as chlorophyll a,soluble protein,SOD,and POD were determined.Among them, SOD had the maximal reduction rate after stress.It was indicated that the stress effects of fenvalerate and its enantiomer s,s-fenvalerate to Platymonas subcordiformis mainly expressed on the suppression of the enzyme.
本实验使用微乳电动毛细管色谱方法,采用β-环糊精作为手性选择剂,成功地进行了氰戊菊酯对映异构体的手性拆分。通过优化实验条件如缓冲溶液的组成、浓度、pH,微乳的组成及浓度,环糊精浓度等,得到最佳拆分参数:选用57cm(有效长度50cm)×75μm(内径)的石英毛细管,分离温度为25℃,分离电压为15KV,β-环糊精的浓度为30mmol/L,缓冲溶液pH=6.5(5mmol/L磷酸二氢钠+10mmol/L硼砂溶液),以140mmol/L十二烷基硫酸钠+30mmol/L正庚烷+300mmol/L正丁醇为微乳。在此条件下可使氰戊菊酯的4个对映体基线分离,并通过内标法确定出S,S-氰戊菊酯的峰型归属。
本实验还考察了氰戊菊酯及S,S-氰戊菊酯对扁藻的96h急性毒性实验。结果显示:氰戊菊酯和S,S-氰戊菊酯对扁藻的生长情况,表现为低浓度刺激,高浓度抑制。氰戊菊酯的96hEC_(50)为39.2mg/L,S,S-氰戊菊酯96hEC_(50)为5.9mg/L。两者相差6.6倍,后者对扁藻的毒性作用大于前者。进而测定了在不同浓度氰戊菊酯和S,S-氰戊菊酯胁迫作用下扁藻的各生理指标(叶绿素a,可溶性蛋白质,超氧化物歧化酶(SOD),过氧化物酶(POD)),其中SOD在胁迫前后的下降率最大,说明氰戊菊酯和S,S-氰戊菊酯对扁藻的胁迫作用主要表现在对酶的抑制作用。
This work has developed a quick method for chiral separation of fenvalerate enantiomers using Microemulsion Electrokinetic Chromatography(MEEKC).By investigating the stress effects of fenvalerate and its enantiomer s,s-fenvalerate on Platymonas subcordiformis,it is known that the chiral separation of fenvalerate enantiomers can reduce the emitted amounts of fenvalerate into the environment and is also valuable for the protection of food chain and the food safety.
Four fenvalerate enantiomers were resolved in the baseline separation by MEEKC usingβ-cyclodextrin as a chiral selector.The electrophoretic experiment parameters such as the buffer components,buffer concentration and pH,the components and concentration of microemulsion,and the concentration ofβ-cyclodextrin were optimized.An uncoated fused-silica capillary of 75μm i.d and length of 57cm(effective 50cm) was used.The capillary temperature was maintained at 25℃,and the sample was separated at 15KV.The optimal separation conditions were achieved with a background electrolyte of 5mmol/L NaH_2PO_4+10mmol/L borax (pH6.5),and the microemulsion of 140mmol/LSDS+30mmol/L n-heptane+300 mmol/L.1-butanol.Further,the peaks of s,s-fenvalerate was confirmed by internal standard method in this electrophoresis conditions.
This work also evaluated 96 hours acute toxicity of fenvalerate and s,s-fenvalerate for Platymonas subcordiformis.According to the experimental results, the 96hEC_(50) of fenvalerate was 39.2mg/L and the 96hEC_(50) of s,s-fenvalerate was 5.9mg/L.The former was 6.6 times high than the latter.The toxicity of s,s-fenvalerate was greater than fenvalerate.The physiological indexes of Platymonas subcordiformis such as chlorophyll a,soluble protein,SOD,and POD were determined.Among them, SOD had the maximal reduction rate after stress.It was indicated that the stress effects of fenvalerate and its enantiomer s,s-fenvalerate to Platymonas subcordiformis mainly expressed on the suppression of the enzyme.
引文
[1]肖军,赵景波.农药污染对生态环境的影响及防治对策.安徽农业科学,2005,33(12):2376-2377.
[2]华小梅.我国农药环境污染与危害的特点及控制对策.环境科学研究,20003,(13):40-43.
[3]何丽莲,李元.农田土壤农药污染的综合治理.云南农业大学学报,2003,1(84):430-434.
[4]高玉荣.杀虫剂单甲脒对绿藻的毒性研究.环境科学学报,1995,15(1):92-97.
[5]BRADBURY S P,SYMONIK D M,COATS J R et al.Toxicity of Fenvalerate and Its Constituent Isomers to the Fathead Minnow,Pimephales Promelas,and Bluegill,Lepomis Macrochirus.Bull.Environ.Contam.Toxicol.,1987,38(3):727-735.
[6]Zidan Z n,Selim A A,Afifi F A et al.Persistence of chlorpyrifos and fenvalerate insecticides in different soil and water types in laboratory.Bulletin of the Entomological Society of Egypt.Economic Series,1991-1992,(19):121-130.
[7]Leslie A R.Field evaluation of the persistence and efficacy of pesticides used for termite control.American Chemical Society,1993,46-61.
[8]Gold R E,Howell N J,Pawson B Met al.Persistence and bioavailability of term iticides to subteranean term ites(Isoptera:Rhinotermitidae)from five soil types and locations in Texas.Proceedings of the North American termite biology and control conference,Nassau,Bahamas,Sociobiology,1996,28(3):337-363.
[9]甘剑英,孙锦荷.氰戊菊酯在土壤和玉米植株中的归趋.浙江农业大学学报,1989,15(1):21-26.
[10]LIU W P,GANJ Y,SCHLENK D et al.Enantiocelectivity in Environmental Safety of Current Chiral Insecticides.PNAS,2005,102(3):701-706.
[11]YIN Y W,WANG Z H.Ecotoxicollogical study of fenproapthrin.Annual Report of State Key Laboratory for Freshwater Ecology and Biotechnology of China.Beijing:nternational Academic Publishers,1993.
[12]Gil A E,Feibush B,Charles S R.Separation of enantiomers by gas liquid chromatography with an optically active stationary phase.Tetrahedron Letters,1966,7(10):1009-1015.
[13]Oehme M,Muller,L,Karlsson H.High-resolution gas chromatographic test for the characterisation of enantioselective separations of organochlorine compounds:Application to tert.-butyldimethylsilyl β-cyclodextrin,Journal of Chromatography A,1997,775:275-285.
[14]Walter V,Ulrike K.Use of 6-O-tert.-butyldimethylsilylated β-cyclodextrins for the enantioseparation of chiral organochlorine compounds,Journal of Chromatography A,1999(846):375-81.
[15]史雪岩,王敏.几种拟除虫菊酸甲酯对映体的毛细管气相色谱手性拆分.分析化学,2002,(11):1293-1297.
[16]赵春霞,王清海,周良模等.除虫剂二氯菊酸甲酯的手性分离.分析化学,2000,28(2):172-175
[17]董晓渭,许旭.气相色谱法手性拆分氯代和溴代环氧苯乙烷.有机化学,2004,3(24):306-309
[18]Okamoto Y,Kawashima M et al.Chromatographic resolution ⅩⅠ Controlled chiral recognition of cellulose triphenylcarbamate derivatives supported on silica gel.Journal of Chromatography,1986,363:173-186.
[19]William L,Champion J,James Lee.Liquid chromatographic separation of the enantiomers of trans-chlordane,cis-chlordane,heptachlor,heptachlor epoxide and α-hexachlorocyclohexane with application to small-scale preparative separation.Journal of Chromatography A,2004,1024:55-62.
[20]邱静,周志强.高效液相色谱法对氯氟吡氧乙酸1-甲基庚酯对映体的拆分.农药学学报,2004,6(2):84-86.
[21]周志强,王鹏.涂敷型淀粉类液相色谱手性固定相对丙烯菊醇对映体的拆分.色谱,2003,(1):44-45.
[22]侯经国,孟晓荣,何天稀等.农药甲霜灵对映体的高效液相色谱分离及手性拆分热力学研究.分析化学,2003(3):307-310.
[23]塔娜,李想,冯建芳等.拟除虫菊酯类农药的非对映和对映异构体分离.中国环境科学,2006,26(1):87-90.
[24]http://en.wikipedia.org/wiki/Capillary_electrophoresis.html
[25]赵明刚,郝爱友,王建英.环糊精在有机合成中的催化性能.化学通报,2005,68:w086.
[26]Pham T T H,Jos H,Ann V S.Recent advances in pharmaceutical application of chiral capillary electrophoresis.Journal of Pharmaceutical and Biomedical Analysis,2006,41:1-11.
[27]黄宝美,姚程炜,李松等.甲霜灵对映体的高效毛细管电泳拆分.应用化学学报,2007,24:1343-1345.
[28]游静,陆豪杰.杀鼠灵对映体的高效毛细管电泳手性拆分.分析测试学报,2001,3:59-61.
[29]刘玉,顾俊岭.γ-环糊精-SDS胶束电动色谱法分离十八甲基炔诺酮光学异构体.色 谱,1995,9:387-389.
[30]许旭,张梅.用去氧胆酸盐和β-环糊精的毛细管胶束电动色谱拆分手性药物.色谱,1998,9:379-382.
[31]郑妍鹏,宋晓虹.胶束电动毛细管色谱法拆分肾上腺素对映体.应用化学,2004,1:16-19.
[32]Watarai H.Microemulsion Capillary Electrophoresis.Chemistry letters,1991,231(3):391-394.
[33]Promod K,Mittal K L.Handbook of Microemulsion Science and Technology.New York:Marcel Dekker,1999.
[34]蒋雪梅,魏为力.微乳液电动色谱测定油-水分配系数的改进方法研究.高等学校化学学报,2006,8:1424-1429.
[35]Tao B,Zhong L,Li M et al.Separations of Isoquinoline Alkaloids and Saponins by Microemulsion Electrokinetic Chromatography with Anionic and Cationic Surfactant.Chromatographia,2002,56:709-716.
[36]薄涛,贡素萱.微乳电动毛细管色谱分离山酮类化合物的影响因素.色谱,2003,21:439-445.
[37]赵艳芳,罗兴平,明永飞等.微乳液毛细管电动色谱法快速测定消炎利胆片中穿心莲内酯和脱水穿心莲内酯.色谱,2006,24:294-297.
[38]张裕平,李向军,袁倬斌.毛细管电泳法分析西维冈等农药.色谱,2002,20:341-344.
[39]范瑞芳.色谱技术在农药手性拆分中的应用.化学通报,2005,68:w005.
[40]朱文涛,邱静.手性农药立体选择性环境行为研究进展.农药与环境安全国际会议论文集,78-82.
[41]Liu W P,Gan J,Lee S J et al.Isomer Selectivity in Aquatic Toxicity and Biodegradation of Bifenthrin and Permethrin.Environmental Toxicology and Chemistry,2005,24(8):1861-1866.
[42]Liu W P,Gan J.Separation and Aquatic Toxicity of Enantiomers of Four Organophosphorus Insecticides.The 226th Annual Meeting of America Chemical Society.USA,2004:137.
[43]William A M.The levo enantiomer of o,p′-DDT inhibits the binding of 17β-estradiol to the estrogen receptor.Life Sciences,1987,40(2):215-221.
[44]刘维屏,徐超,周珊珊.手性污染物与环境安全.环境化学,2006,3:247-251.
[45]马云,刘维屏.手性污染物环境行为的对映体筹异性.环境污染治理技术与设备,2002,11:4-9.
[46]王宝利,刘丛强.水体内藻类的生物地球化学.矿物岩石地球化学通报,2004,23(1): 79-82.
[47]Kobraei M E,White D S.Effects of 2,4-Dichlorohenoxyacetic acid on Kentucky algae:simultaneous laboratory and field toxicity testings.Arch Environ Contam Toxicol,1996,31:571-580.
[48]Ferrardo M D.Chronic toxicity of fenitrethion to an aglae(Nannchloris oculata),a rotifer(Brachionus calyci-florus) and the cladoceran(Daphnra magna).Ecotoxicol and Environ Safety,1996,35:112-120.
[49]Megharaj M,Venkateswarlu K.Influence of cypermethrin and fenvalerate on a green alga and three cyanobacteria isola-ted from soil.Ecotoxicology and Environmental Safety,1987,14(2):142-146.
[50]陈碧鹃,陈民山.氰戊菊酯、胺菊酯对海洋藻类、贝类的毒性研究.中国水产科学,1997,4(2):51-55.
[51]熊丽,吴振斌,况琪军等.氯氰菊酯对斜生栅藻的毒性研究.水生生物学报,2002,26(1):66-73.
[52]http://baike.baidu.com/view/776011.html
[53]http://www.bio.utexas.edu/research/utex/photogallery/t-z/TetraSelmis_chuii_232.html
[54]陈义编著.毛细管电泳技术及应用(第二版).北京:化学工业出版社,2005,11(4):54.
[55]Kevin D A.Background theory and applications of microemulsion electrokinetic chromatography.Journal of Chromatography A,2000,892:171-186.
[56]Alex M,Brian C.Recent advances in microemulsion electrokinetic chromatography.Electrophoresis,2004,25:3970-3980.
[57]KLOTZ W.L,SCHURE M.R,FOLEY J.P.Determination of octanol-water partition coefficients of pesticides by microemulsion electrokinetic chromatography.Journal of Chromatography A,2001,930:145-154.
[58]Rainer S,Wolfgang B.Systematic investigations of different capillary electrophoretic techniques for separation of methylquinolines.J.Sep.Sci.,2003,26:1247-1252.
[59]GABEL J C,HANSEN S H,PEDERSEN B S.Separation of neutral compounds by microemulsion electrokinetic chromatography:Fundamental studies on selectiveity.Electrophoresis,2001,22(7):1330-1336.
[60]张宣,胡亚男,王义明等.蛋白质的微乳液毛细管电动色谱分离研究.高等学校化学学报,2000,21(8):1183-1186.
[61]Altria K D,Clark B J,Mahuzier P E.The effect of operating variables in microemulsion electrokinetic capillary chromatography.Chromatographia,2000,52:758-768.
[62]Ivanova M,Piunti A,Marziali E.Microemulsion electrokinetic chromatography applied for separation of levetiracetam from other antiepileptic drugs in polypharmacy.Electrophoresis,2003,24:992-998.
[63]塔娜,李想.拟除虫菊酯类农药的非对映和对映异构体分离.中国环境科学,2006,26(1):87-90.
[64]LI G S,QING Y O,WEI L Y et al.Separation of six phenylureas and chlorsulfuron standards by micellar,mixed micellar and microemulsion electrokinetic chromatography.Journal of Chromatography A,1995,699(1):371.
[65]Takashi K,Kazuki K,Totaro I.Detection of 27 Molecules in a Single Injection Volume by Hadamard Transform Capillary Electrophoresis.Analytical Sciences,2003,12(19):1659-1661.
[66]ZHUJ P,,HUC Q,LIU W Y.Study on Factors Affecting Reproducibility of Migration Time in Capillary Electrophoresis.Chinese Journal of Chromatography,2006,24(4):396-401.
[67]Pham T T H,Jos H,Ann V S.Recent advances in pharmaceutical application of chiral capillary electrophoresis.Journal of Pharmaceutical and Biomedical Analysis,2006,41:1-11.
[68]刘润国.产氢扁藻的培养优化:(硕士论文).大连:中国科学院大连化学物理研究所,2004.
[69]赵玉艳,蔡磊明.几种藻类毒性试验统计方法的差异.农药,2004,43(7):298-299.
[70]黄国兰,戴树桂.有机污染物对藻类毒性的测定.环境化学,1994,13(3):259-262.
[71]阎海,叶常明.蛋白核小球藻与单甲脒的相互作用.环境化学,1995,14(4):350-353.
[72]安胜利,莫一心,欧春泉.在SPSS10.0软件上进行概率单位分析.第一军医大学学报,2002,22(11):1019-1021.
[73]张志良.植物生理学实验指导(第3版).北京:高等教育出版社,2003:121-124.
[74]严铁,马建义,王品维.有机溶剂在农药生物测定中对靶标生物的影响.浙江农业科学,2004,2:85-88.
[75]熊丽,吴振斌,况琪军等.氯氰菊酯对斜生栅藻的毒性研究.水生生物学报,2002,26(1):66-73.
[76]唐学玺,颜挺进,李永祺.久效磷对扁藻的损伤作用Ⅰ:扁藻细胞活性氧损伤作用.应用生态学报,1998,9(6):627-630.
[77]褚华东.氰戊菊酯的手性拆分及其对映体的水生毒理学研究:(硕士论文),杭州:浙江大 学,2006.
[78]刘涛,熊丽,生秀梅等.高效氯氰菊酯对斜生栅藻的毒性研究.化学与生物工程,2006,23(7):37-39.
[79]Alberte R S.Waterstress effects on the content and organization of chlorophyll in Mesophyll and bundle sheach chlorolplasts of maize.Plant Physial.,1997,(59):351-353.
[80]陈传红,刘振乾,傅凤等.丁草胺对杜氏盐藻生理生化的影响.生态科学,2007,26(1):18-21.
[81]唐学玺,颜挺进,李永祺等.久效磷对扁藻的损伤作用Ⅱ:叶绿素a降解与活性氧损伤的相关性.应用生态学报,1998,9(6):631-634.
[2]华小梅.我国农药环境污染与危害的特点及控制对策.环境科学研究,20003,(13):40-43.
[3]何丽莲,李元.农田土壤农药污染的综合治理.云南农业大学学报,2003,1(84):430-434.
[4]高玉荣.杀虫剂单甲脒对绿藻的毒性研究.环境科学学报,1995,15(1):92-97.
[5]BRADBURY S P,SYMONIK D M,COATS J R et al.Toxicity of Fenvalerate and Its Constituent Isomers to the Fathead Minnow,Pimephales Promelas,and Bluegill,Lepomis Macrochirus.Bull.Environ.Contam.Toxicol.,1987,38(3):727-735.
[6]Zidan Z n,Selim A A,Afifi F A et al.Persistence of chlorpyrifos and fenvalerate insecticides in different soil and water types in laboratory.Bulletin of the Entomological Society of Egypt.Economic Series,1991-1992,(19):121-130.
[7]Leslie A R.Field evaluation of the persistence and efficacy of pesticides used for termite control.American Chemical Society,1993,46-61.
[8]Gold R E,Howell N J,Pawson B Met al.Persistence and bioavailability of term iticides to subteranean term ites(Isoptera:Rhinotermitidae)from five soil types and locations in Texas.Proceedings of the North American termite biology and control conference,Nassau,Bahamas,Sociobiology,1996,28(3):337-363.
[9]甘剑英,孙锦荷.氰戊菊酯在土壤和玉米植株中的归趋.浙江农业大学学报,1989,15(1):21-26.
[10]LIU W P,GANJ Y,SCHLENK D et al.Enantiocelectivity in Environmental Safety of Current Chiral Insecticides.PNAS,2005,102(3):701-706.
[11]YIN Y W,WANG Z H.Ecotoxicollogical study of fenproapthrin.Annual Report of State Key Laboratory for Freshwater Ecology and Biotechnology of China.Beijing:nternational Academic Publishers,1993.
[12]Gil A E,Feibush B,Charles S R.Separation of enantiomers by gas liquid chromatography with an optically active stationary phase.Tetrahedron Letters,1966,7(10):1009-1015.
[13]Oehme M,Muller,L,Karlsson H.High-resolution gas chromatographic test for the characterisation of enantioselective separations of organochlorine compounds:Application to tert.-butyldimethylsilyl β-cyclodextrin,Journal of Chromatography A,1997,775:275-285.
[14]Walter V,Ulrike K.Use of 6-O-tert.-butyldimethylsilylated β-cyclodextrins for the enantioseparation of chiral organochlorine compounds,Journal of Chromatography A,1999(846):375-81.
[15]史雪岩,王敏.几种拟除虫菊酸甲酯对映体的毛细管气相色谱手性拆分.分析化学,2002,(11):1293-1297.
[16]赵春霞,王清海,周良模等.除虫剂二氯菊酸甲酯的手性分离.分析化学,2000,28(2):172-175
[17]董晓渭,许旭.气相色谱法手性拆分氯代和溴代环氧苯乙烷.有机化学,2004,3(24):306-309
[18]Okamoto Y,Kawashima M et al.Chromatographic resolution ⅩⅠ Controlled chiral recognition of cellulose triphenylcarbamate derivatives supported on silica gel.Journal of Chromatography,1986,363:173-186.
[19]William L,Champion J,James Lee.Liquid chromatographic separation of the enantiomers of trans-chlordane,cis-chlordane,heptachlor,heptachlor epoxide and α-hexachlorocyclohexane with application to small-scale preparative separation.Journal of Chromatography A,2004,1024:55-62.
[20]邱静,周志强.高效液相色谱法对氯氟吡氧乙酸1-甲基庚酯对映体的拆分.农药学学报,2004,6(2):84-86.
[21]周志强,王鹏.涂敷型淀粉类液相色谱手性固定相对丙烯菊醇对映体的拆分.色谱,2003,(1):44-45.
[22]侯经国,孟晓荣,何天稀等.农药甲霜灵对映体的高效液相色谱分离及手性拆分热力学研究.分析化学,2003(3):307-310.
[23]塔娜,李想,冯建芳等.拟除虫菊酯类农药的非对映和对映异构体分离.中国环境科学,2006,26(1):87-90.
[24]http://en.wikipedia.org/wiki/Capillary_electrophoresis.html
[25]赵明刚,郝爱友,王建英.环糊精在有机合成中的催化性能.化学通报,2005,68:w086.
[26]Pham T T H,Jos H,Ann V S.Recent advances in pharmaceutical application of chiral capillary electrophoresis.Journal of Pharmaceutical and Biomedical Analysis,2006,41:1-11.
[27]黄宝美,姚程炜,李松等.甲霜灵对映体的高效毛细管电泳拆分.应用化学学报,2007,24:1343-1345.
[28]游静,陆豪杰.杀鼠灵对映体的高效毛细管电泳手性拆分.分析测试学报,2001,3:59-61.
[29]刘玉,顾俊岭.γ-环糊精-SDS胶束电动色谱法分离十八甲基炔诺酮光学异构体.色 谱,1995,9:387-389.
[30]许旭,张梅.用去氧胆酸盐和β-环糊精的毛细管胶束电动色谱拆分手性药物.色谱,1998,9:379-382.
[31]郑妍鹏,宋晓虹.胶束电动毛细管色谱法拆分肾上腺素对映体.应用化学,2004,1:16-19.
[32]Watarai H.Microemulsion Capillary Electrophoresis.Chemistry letters,1991,231(3):391-394.
[33]Promod K,Mittal K L.Handbook of Microemulsion Science and Technology.New York:Marcel Dekker,1999.
[34]蒋雪梅,魏为力.微乳液电动色谱测定油-水分配系数的改进方法研究.高等学校化学学报,2006,8:1424-1429.
[35]Tao B,Zhong L,Li M et al.Separations of Isoquinoline Alkaloids and Saponins by Microemulsion Electrokinetic Chromatography with Anionic and Cationic Surfactant.Chromatographia,2002,56:709-716.
[36]薄涛,贡素萱.微乳电动毛细管色谱分离山酮类化合物的影响因素.色谱,2003,21:439-445.
[37]赵艳芳,罗兴平,明永飞等.微乳液毛细管电动色谱法快速测定消炎利胆片中穿心莲内酯和脱水穿心莲内酯.色谱,2006,24:294-297.
[38]张裕平,李向军,袁倬斌.毛细管电泳法分析西维冈等农药.色谱,2002,20:341-344.
[39]范瑞芳.色谱技术在农药手性拆分中的应用.化学通报,2005,68:w005.
[40]朱文涛,邱静.手性农药立体选择性环境行为研究进展.农药与环境安全国际会议论文集,78-82.
[41]Liu W P,Gan J,Lee S J et al.Isomer Selectivity in Aquatic Toxicity and Biodegradation of Bifenthrin and Permethrin.Environmental Toxicology and Chemistry,2005,24(8):1861-1866.
[42]Liu W P,Gan J.Separation and Aquatic Toxicity of Enantiomers of Four Organophosphorus Insecticides.The 226th Annual Meeting of America Chemical Society.USA,2004:137.
[43]William A M.The levo enantiomer of o,p′-DDT inhibits the binding of 17β-estradiol to the estrogen receptor.Life Sciences,1987,40(2):215-221.
[44]刘维屏,徐超,周珊珊.手性污染物与环境安全.环境化学,2006,3:247-251.
[45]马云,刘维屏.手性污染物环境行为的对映体筹异性.环境污染治理技术与设备,2002,11:4-9.
[46]王宝利,刘丛强.水体内藻类的生物地球化学.矿物岩石地球化学通报,2004,23(1): 79-82.
[47]Kobraei M E,White D S.Effects of 2,4-Dichlorohenoxyacetic acid on Kentucky algae:simultaneous laboratory and field toxicity testings.Arch Environ Contam Toxicol,1996,31:571-580.
[48]Ferrardo M D.Chronic toxicity of fenitrethion to an aglae(Nannchloris oculata),a rotifer(Brachionus calyci-florus) and the cladoceran(Daphnra magna).Ecotoxicol and Environ Safety,1996,35:112-120.
[49]Megharaj M,Venkateswarlu K.Influence of cypermethrin and fenvalerate on a green alga and three cyanobacteria isola-ted from soil.Ecotoxicology and Environmental Safety,1987,14(2):142-146.
[50]陈碧鹃,陈民山.氰戊菊酯、胺菊酯对海洋藻类、贝类的毒性研究.中国水产科学,1997,4(2):51-55.
[51]熊丽,吴振斌,况琪军等.氯氰菊酯对斜生栅藻的毒性研究.水生生物学报,2002,26(1):66-73.
[52]http://baike.baidu.com/view/776011.html
[53]http://www.bio.utexas.edu/research/utex/photogallery/t-z/TetraSelmis_chuii_232.html
[54]陈义编著.毛细管电泳技术及应用(第二版).北京:化学工业出版社,2005,11(4):54.
[55]Kevin D A.Background theory and applications of microemulsion electrokinetic chromatography.Journal of Chromatography A,2000,892:171-186.
[56]Alex M,Brian C.Recent advances in microemulsion electrokinetic chromatography.Electrophoresis,2004,25:3970-3980.
[57]KLOTZ W.L,SCHURE M.R,FOLEY J.P.Determination of octanol-water partition coefficients of pesticides by microemulsion electrokinetic chromatography.Journal of Chromatography A,2001,930:145-154.
[58]Rainer S,Wolfgang B.Systematic investigations of different capillary electrophoretic techniques for separation of methylquinolines.J.Sep.Sci.,2003,26:1247-1252.
[59]GABEL J C,HANSEN S H,PEDERSEN B S.Separation of neutral compounds by microemulsion electrokinetic chromatography:Fundamental studies on selectiveity.Electrophoresis,2001,22(7):1330-1336.
[60]张宣,胡亚男,王义明等.蛋白质的微乳液毛细管电动色谱分离研究.高等学校化学学报,2000,21(8):1183-1186.
[61]Altria K D,Clark B J,Mahuzier P E.The effect of operating variables in microemulsion electrokinetic capillary chromatography.Chromatographia,2000,52:758-768.
[62]Ivanova M,Piunti A,Marziali E.Microemulsion electrokinetic chromatography applied for separation of levetiracetam from other antiepileptic drugs in polypharmacy.Electrophoresis,2003,24:992-998.
[63]塔娜,李想.拟除虫菊酯类农药的非对映和对映异构体分离.中国环境科学,2006,26(1):87-90.
[64]LI G S,QING Y O,WEI L Y et al.Separation of six phenylureas and chlorsulfuron standards by micellar,mixed micellar and microemulsion electrokinetic chromatography.Journal of Chromatography A,1995,699(1):371.
[65]Takashi K,Kazuki K,Totaro I.Detection of 27 Molecules in a Single Injection Volume by Hadamard Transform Capillary Electrophoresis.Analytical Sciences,2003,12(19):1659-1661.
[66]ZHUJ P,,HUC Q,LIU W Y.Study on Factors Affecting Reproducibility of Migration Time in Capillary Electrophoresis.Chinese Journal of Chromatography,2006,24(4):396-401.
[67]Pham T T H,Jos H,Ann V S.Recent advances in pharmaceutical application of chiral capillary electrophoresis.Journal of Pharmaceutical and Biomedical Analysis,2006,41:1-11.
[68]刘润国.产氢扁藻的培养优化:(硕士论文).大连:中国科学院大连化学物理研究所,2004.
[69]赵玉艳,蔡磊明.几种藻类毒性试验统计方法的差异.农药,2004,43(7):298-299.
[70]黄国兰,戴树桂.有机污染物对藻类毒性的测定.环境化学,1994,13(3):259-262.
[71]阎海,叶常明.蛋白核小球藻与单甲脒的相互作用.环境化学,1995,14(4):350-353.
[72]安胜利,莫一心,欧春泉.在SPSS10.0软件上进行概率单位分析.第一军医大学学报,2002,22(11):1019-1021.
[73]张志良.植物生理学实验指导(第3版).北京:高等教育出版社,2003:121-124.
[74]严铁,马建义,王品维.有机溶剂在农药生物测定中对靶标生物的影响.浙江农业科学,2004,2:85-88.
[75]熊丽,吴振斌,况琪军等.氯氰菊酯对斜生栅藻的毒性研究.水生生物学报,2002,26(1):66-73.
[76]唐学玺,颜挺进,李永祺.久效磷对扁藻的损伤作用Ⅰ:扁藻细胞活性氧损伤作用.应用生态学报,1998,9(6):627-630.
[77]褚华东.氰戊菊酯的手性拆分及其对映体的水生毒理学研究:(硕士论文),杭州:浙江大 学,2006.
[78]刘涛,熊丽,生秀梅等.高效氯氰菊酯对斜生栅藻的毒性研究.化学与生物工程,2006,23(7):37-39.
[79]Alberte R S.Waterstress effects on the content and organization of chlorophyll in Mesophyll and bundle sheach chlorolplasts of maize.Plant Physial.,1997,(59):351-353.
[80]陈传红,刘振乾,傅凤等.丁草胺对杜氏盐藻生理生化的影响.生态科学,2007,26(1):18-21.
[81]唐学玺,颜挺进,李永祺等.久效磷对扁藻的损伤作用Ⅱ:叶绿素a降解与活性氧损伤的相关性.应用生态学报,1998,9(6):631-634.
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |