β-环糊精修饰的纳米金粒子在毛细管电色谱手性分离中的应用研究
|
摘要
毛细管电泳以其分离效率高,分离速度快,操作模式多等特点,迅速发展成为一种极其有效的分离技术,在分离分析方面具有十分重要的作用和广泛的应用前景。本论文主要研究了以巯基环糊精修饰的纳米金粒子作为准固定相的毛细管电色谱(CEC)在手性分离中的应用,旨在建立一种高效、灵敏、快速、低耗的毛细管电色谱手性分离的方法。本论文的研究工作主要集中在以下几个部分:
(1)合成水溶性的、分布均匀的、稳定性好的巯基环糊精修饰的纳米金粒子(β-SH-CD modified GNPs),并通过透射电镜(TEM),核磁共振(HNMR),红外(FT-TR)以及紫外光谱(UV)进行表征。
(2)以合成的巯基环糊精修饰的纳米金粒子为准固定相,利用高效毛细管电色谱技术对几种典型的天然手性氨基酸进行拆分。优化缓冲溶液pH值、分离电压、纳米金粒子浓度等实验条件。以极低的纳米金粒子浓度(如1.0mg/mL,仅相当于0.38 mM环糊精)即可达到基线分离。
(3)以合成的巯基环糊精修饰的纳米金粒子为准固定相,利用高效毛细管电色谱技术对几种市售手性药物进行拆分。优化实验条件,同样以极低的纳米金粒子浓度(如0.8mg/mL,仅相当于0.30 mM环糊精)即可达到基线分离。
(4)采用毛细管电泳紫外检测技术分析分离了爆炸残余物无机阴阳离子和一些有机物。通过快速、准确检验鉴定爆炸残余物痕量成份,准确地认定炸药种类,能够为侦破爆炸案件提供线索和证据。
Capillary electrophoresis is a useful separation technology and has been applied to many Fields,owing to its characteristics:high efficiency separation,high speed analysis,more manipulation mode and et al.Applications of thiolated-β-cyclodextrin modified gold nanopar- ticles for chiral separation based on capillary electrochromatography were studied in this article which aimed at establishing an analysis method of efficiency separation,high speed analysis and low consumption.It includes some parts in this research work:
(1)A classics method was introduced in synthesizing thiolated-β-cyclodextrin modified gold nanoparticles of which were water soluble,homogenized and good stability.And they were characterized by TEM,NMR,FT-TR and UV absorption spectroscopy.
(2)Use the synthesized of thiolatedβ-cyclodextrin modified gold nanoparticles as pseudostationary phase for amino acid enantioseparation based on capillary electrochromato- graphy was studied in this chapter.Experimental conditions of buffer pH,separation voltage and concentration of GNPs were optimized.Baseline separation was received at very low concentration of GNPs(such as 1.0mg/mL,to be equivalent to 0.38 mM ofβ-CD).
(3)Use the synthesized of thiolatedβ-cyclodextrin modified gold nanoparticles as pseudostationary phase for drugs enantioseparation based on capillary electrochromatography was studied in this chapter.Experimental conditions were optimized.Baseline separation was received at very low concentration of GNPs(such as 0.8mg/mL,to be equivalent to 0.30 mM ofβ-CD).
(4)Some inorganics and organics in explosives residue were analyzed by capillary electrophoresis.It could be confirmed accurately that the kind of explosives by experiment which could apply clues and evidences for cases of exploding.
(1)合成水溶性的、分布均匀的、稳定性好的巯基环糊精修饰的纳米金粒子(β-SH-CD modified GNPs),并通过透射电镜(TEM),核磁共振(HNMR),红外(FT-TR)以及紫外光谱(UV)进行表征。
(2)以合成的巯基环糊精修饰的纳米金粒子为准固定相,利用高效毛细管电色谱技术对几种典型的天然手性氨基酸进行拆分。优化缓冲溶液pH值、分离电压、纳米金粒子浓度等实验条件。以极低的纳米金粒子浓度(如1.0mg/mL,仅相当于0.38 mM环糊精)即可达到基线分离。
(3)以合成的巯基环糊精修饰的纳米金粒子为准固定相,利用高效毛细管电色谱技术对几种市售手性药物进行拆分。优化实验条件,同样以极低的纳米金粒子浓度(如0.8mg/mL,仅相当于0.30 mM环糊精)即可达到基线分离。
(4)采用毛细管电泳紫外检测技术分析分离了爆炸残余物无机阴阳离子和一些有机物。通过快速、准确检验鉴定爆炸残余物痕量成份,准确地认定炸药种类,能够为侦破爆炸案件提供线索和证据。
Capillary electrophoresis is a useful separation technology and has been applied to many Fields,owing to its characteristics:high efficiency separation,high speed analysis,more manipulation mode and et al.Applications of thiolated-β-cyclodextrin modified gold nanopar- ticles for chiral separation based on capillary electrochromatography were studied in this article which aimed at establishing an analysis method of efficiency separation,high speed analysis and low consumption.It includes some parts in this research work:
(1)A classics method was introduced in synthesizing thiolated-β-cyclodextrin modified gold nanoparticles of which were water soluble,homogenized and good stability.And they were characterized by TEM,NMR,FT-TR and UV absorption spectroscopy.
(2)Use the synthesized of thiolatedβ-cyclodextrin modified gold nanoparticles as pseudostationary phase for amino acid enantioseparation based on capillary electrochromato- graphy was studied in this chapter.Experimental conditions of buffer pH,separation voltage and concentration of GNPs were optimized.Baseline separation was received at very low concentration of GNPs(such as 1.0mg/mL,to be equivalent to 0.38 mM ofβ-CD).
(3)Use the synthesized of thiolatedβ-cyclodextrin modified gold nanoparticles as pseudostationary phase for drugs enantioseparation based on capillary electrochromatography was studied in this chapter.Experimental conditions were optimized.Baseline separation was received at very low concentration of GNPs(such as 0.8mg/mL,to be equivalent to 0.30 mM ofβ-CD).
(4)Some inorganics and organics in explosives residue were analyzed by capillary electrophoresis.It could be confirmed accurately that the kind of explosives by experiment which could apply clues and evidences for cases of exploding.
引文
[1] Dun H J,Song X Q,ChenL R.Preparation of derivatized cellulose coated ZrO2/SiO2 and direct chiral resolution of alpha-biphenyl dicarboxylante compounds by BPLC[J].Acta Chimica Sinica,2003,61(8):1326.
[2] Gross G M,Grate J W,Synovec RE.Monolayer-protected gold nanoparticles as an efficient stationary phase for open tubular gas chromatography using a square capillary model for chip-based gas chromatography in squarecornered microfabricated channels[J].Journal of chromatography A,2004,1029,185.
[3]罗国安,王义明.毛细管电泳的原理及应用第一讲毛细管电泳简介[J].色谱,1995,13(4):254-256.
[4] Walbmehl Y,Jorgenson J W.On-column UV absorption detector for open tubular capillary zone electrophoresis[J].J Chromatogr A,1984,315,135-143.
[5] Mathies R A,Huang X C.Capillary array electrophoresis:an approach to high-speed,high throughput DNA sequencing[J].Nature,1992,359,167-169.
[6]董捷.毛细管电泳在生物分析化学上的应用及进展[J].山东环境,1998,19-20.
[7]黄少平.高效毛细管电泳法在药物分析及体内分析中的应用[J].中华临床医学研究杂志,2006,12(9):1246-1249.
[8]毛煜,徐建明.毛细管电泳技术和应用新进展[J].化学研究与应用,2001,13(1):4-9.
[9] Yan C,Dadoo R,Zare R N,et al.Gradient Elution in Capillary Electrochromatography[J].Anal Chem,1996,68(17):2726-2730.
[10]夏仕文,李树本.酶在光学活性药物合成中的应用[J].合成化学,1996,4(3):201-207.
[11]Laird T.Delelopment chemistry at its best [M].Chem Ind (London),1989,366-367.
[12]继成.我国医药原料和中间体发展动向[J].中国制药信息,1998,14(12):28-31.
[13]肖畴阡,宋光泉.有机化学[M].广州:中山大学出版社,1996,196.
[14]尹国,刘振华,曾姗姗,等.手性异构体拆分方法的研究进展[J].中国药物化学杂志,2001,11(1):57.
[15]姜廷福,陈豪杰,梁冰,等.毛细管电泳分离液相手性药物[J].药物分析杂志,2002,22(3):245-248.
[16]Terabe S,Otsuka K,Nishi H.Separation of enantiomers by capillary electrophoretic techniques[J].J Chromatogr,1994,666,295-319.
[17]陈义.毛细管电泳技术及应用[M].化学工业出版社,2000,103-105.
[18]Tran A D,Blanc T,Leopold E J.Micellar electrokinetic chromatography:methodological and instrumental advances [J].J Chromatogr,1990,516,241.
[19]Lurie I S.Micellar electrokinetic capillary chromatography of the enantiomers of amphetamine,methamphetamine and their hydroxyphenethylamine precursors[J].J Chromatogr,1992,605,269.
[20]Szejtli J.Introduction and General Overview of Cyclodextrin Chemistry[J].Chem Rev,1998,98(5):1743-1754.
[21]Van Eeckhaut A,Michotte Y.Chiral separations by capillary electrophoresis:Recent developments and applications[J].Electrophoresis,2006,27,2880-2895.
[22]Gubitz G,Schmild M G.Chiral separation principles in capillary electrophoresis[J].J Chromatogr A, 1997,792,179-225.
[23]Fanali S.Identification of chiral drug isomers by capillary electrophoresis[J].J Chromatogr A,1996,735,77-121.
[24]Gubltz G , SchmidM G . Recent Progress In Chiral Separation Principles In Capillary Electrophoresis[J].Electrophoresis,2000,21,4112-4135.
[25]Van Eeckhaut A,Deteaevmier M R,J Crommen,et al.Differential effects of organic modifiers on the enantioseparation of dimetindene maleate with carboxymethyl-β-cyclodextrin in capillary Electrophoresis[J].J SeP Sci,2004,27,21-27.
[26]Wang Z Y,Tang Z M,Z H Gu,et al.Enantioseparation of chiral allenic acids by micellar electrokinetic chromatography with cyclodextrins as chiral selector[J].Electrophoresis,2005,26,1001-1006.
[27]杨郁,郭良宏.超分子主体化合物环糊精应用于环境污染物分离分析的研究进展[J].科学通报,2009,54(2):128-137.
[28]刘夺奎,顾振亚,董振礼.环糊精在纺织染整加工中应用的新进展[J].染整技术,2003,25(3):12-15.
[29]刘旭海.中药制备新技术[J].工艺探讨与系统设计,2009,26.
[30]林向成,赵书林.氨基酸和多巴对映体的毛细管电泳手性拆分新体系研究[D].广西师范大学, 2004.
[31]Fanali S.Separation of optical isomers by capillary zone electrophoresis based on host-guest complexation with cyclodextrins[J].J Chromatogr,1989,474,441-446.
[32]Tanaka M,et al.Enantiomeric separation of dansylamino acids by capillary zone electrophoresis based on complexation with cyclodextrins[J].Fresenius J Anal Chem,1992,339,896.
[33]Yamashoji Y,et al.Chiral recognition and enantiomeric separation of alanineβ-naphthylamide by cyclodextrins[J].Anal Chem Acta,1992,268,39.
[34]Schmitt T,Engelhard H.Derivatized cyclodextrins for the separation of enantiomers in capillary electrophoresis[J].HRC,1993,16,525.
[35]Peterson T E,Trowbridge D.Quantitation of l-epinephrine and determination of the d-/l-epinephrine enantionmer ratio in a pharmaceutical formulation by capillary electrophoresis[J].J Chromatogr,1992,603,298.
[36]Peterson T E.Separation of drug stereoisomers by capillary electrophoresis with cyclodextrins[J].J Chromatogy,1993,630,353.
[37]Fanali S,Bocek P.Enantiomer resolution by using capillary zone electrophoresis.Resolution of racemic tryptophan and determination of the enantiomer composition of commercial pharmaceutical epinephrine[J].Electrophoresis,1990,11,757.
[38]Quang C,Khaladi G.Compounds in Capillary Electrophoresis.Using b-cyclodextrin and Tetraalkyl- ammonium Reagents[J].Anal Chem,1993,65,3354.
[39]Quang C,Khalidi G.Direct separation of the enantiomers of -blockers by cyclodextrin-mediated capillary zone electrophoresis[J].HRC,1994,17,99.
[40]Heuermann M,Blaschke G.Chiral separation of basic drugs using cyclodextrins as chiral pseudo- stationary phases in capillary electrophoresis[J].J Chromatogr,1993,648,267.
[41]Nishi H, et al.Chiral separation of drugs using cyclodextrins in capillary zone electrophoresis[J].J Chromatogr,1994,659,449.
[42]Penn S G,et al.Differential binding of tioconazole enantiomers to hydroxypropyl-β-cyclodextrin studied by capillary electrophoresis[J].J Chromatogr,1993,636,149.
[43]Wren S A C,Rowe R C.Theoretical aspects of chiral separation in capillary electrophoresis:III.Application toβ-blockers[J].J Chromatogr A,1993,635,113.
[44]Nielen M W F.Chiral separation of basic drugs using cyclodextrin-modified capillary zone electrophoresis[J].Anal Chem,1993,65,885.
[45]Schutzner W , Fanali S . Enantiomers resolution in capillary zone electrophoresis by using cyclodextrins[J].Electrophoresis,1992,13,687.
[46]Palmarsdottir S,Edholm L E.Capillary zone electrophoresis for separation of drug enantiomers using cyclodextrins as chiral selectors:Influence of experimental parameters on separation[J].J Chromatogr,1994,666,337.
[47]Schneiderman E,Gratz S R,Stalcup A M.Optimization of preparative electrophoretic chiral separation of ritalin enan-tiomers[J].J Pharm Biomed Anal,2002,27(324):639-650.
[48]Awadallah B,Schmidt P C,Holzgrabe U,et al.Quantitation of talinolol and otherβ-CD-blockers by capillary elec-trophoresis for in vitro drug absorption studies[J].Electrophoresis,2003,24(15):2627-2632.
[49]Paias F O,Bondato P S.Enantioselective analysis of hydrox-ymebendazole in plasma by high- performance liquid chro-matography and capillary electrophoresis[J].Electrophoresis,2003,25(15217):1063-1069.
[50]Pham T T H,Schepdael A V,Hauta-aho T,et al.Simultaneous determination of dopa and carbidopa enantiomers by capillary zone electrophoresis[J].Electrophoresis,2003,23(19):3404-3409.
[51]Jabor V A P,Lanchote V L,Bonato P S.Enantioselective analysis of ibuprofen in human plasma by anionic cyclodextrin-modified electrokinetic chromatography [J].Electrophoresis,2003,23(17):3041-3047.
[52]Viberg P,Jornten Karlsson M,Petersson P.Nanoparticles as pseudostationary phase in capillary electrochromatography/ESI-MS[J].Anal Chem,2002,74,4595-4601.
[53]FujimotoY,MuranakaY.Electrokinetic chromatography using nanometer-sized silica particles as the dynamic stationary phase[J].J High Resolut Chromatogr,1997,20,400-402.
[54]Reynold KJ,ColonLA.Submicron sized organo-silica spheres for capillary electrochromatography[J]. J Liq Chromatogr Relat Teehnol,2000,23,161-173.
[55]Luong J H T,BouvretteP,LiuY L,et al.Electrophoretic separation of aniline derivatives using fused silica capillaries coated with acid treated single-walled carbon nanotubes[J].J Chromatogr A,2005,1074,187-194.
[56]Mahony T O , OwensV P , et al . Alkylthiol gold nanparticles in open-tubular capillary eleetrochromatogr-aphy [J].J Chromatogr A,2003,1004,181-193.
[57]Yang L,Guihen E,et al.Gold nanoparticle-modified etched capillary for open-tubular capillary electrochromatography[J].Anal Chem 2005,77,1840-1846.
[58]GrossG M,NelsonD A,Grate J W,etal.Monolayer-protected gold nanoparticles as a stationary phase for open tubular gas chromatography[J].Anal Chem,2003,75,4558-4564.
[1] Frens G.Controlled Nucleation for the Regulation of the Partiele Monodis Perse Gold Suspensions [J].Nature:Phys Sci,1973,241,20-22.
[2] Natan M J,et a1.Morphology-Dependent Electrochemistry of Cytochrome c at Au Colloid-Modified SnO2 Electrodes[J].J Am Chem Soc,1996,118,1154.
[3] Yonezawa T,Sutoh M,Kunitake T.Practieal Preparation of Size-Controlled GoldNano Particles In Water[J].Chem Lett,1997,7,619-620.
[4] Yonezawa T,Kunitake T.Practical Preparationof Anionic Mereapto Ligand-Stabilized Gold Nano- Particles and Their Immobilization[J].Colloids Surf A:Physicochem Eng Aspeets,1999,149,193-199.
[5] Carotenuto G,Nieolais L.Size-controlled sythesis of Thiol-Derivatized Gold Clusters[J].J Mater Chem,2003,13,1038-1041.
[6] Pengo P,Polizzi S,Battagliarin M,et al.Synthes,Characterization and Properties of Water-Soluble Gold Nano Particles withTunable Core Size[J].J Mater Chem,2003,13,2471-2478.
[7] BrownK R,Natan M J.Hydroxylamine Seeding of Colloidal An NanoParticles in Solution and on Surfaces[J].Langmuir,1998,14,726-728.
[8]朱梓华,朱涛,刘忠范.大粒径单分散金纳米粒子的水相合成[J].物理化学报,1999,15,966-970.
[9] SaundersA E,SiglnanM B Jr,KorgelB A.Growth kinetics and Metastability of MonodisPerse Tetraoetylammonium Bromide Capped Gold Nanocrystals[J].J Phys Chem B,2004,108,193-199.
[10]Sayd B,PrashantV K,Surat H.Photoinduced EleetronTransfer between Chlorophylla and Gold Nanoparticles[J].J Phys Chem B,2005,109,16-723.
[11]Jin R,Wu G,Li Z,et al.What Controls the Melting Properties of DNA-Linked Gold NanoParticle Assemblies[J].J Am Chem Soc,2003,125,1643-1654.
[12]Brust M,Walker M,et al.Synthesis of Thiol Derivatised Gold Nanoparticles in a Two Phase Liquid/Liquid System[J].J Chem Soc Chem Commun,1994,7,801.
[13]Fullam S,Rao SN,Fitzmaurice D.Noncovalent Self-Assembly of Silver Nanocrystal Aggregates in Solution[J].J Phys Chem B,2000,104,6164.
[14]Boal A K , Rotello V M . Redox-Modulated Recognition of Flavin by Functionalized Gold Nanoparticles[J].J Am Chem Soc,1999,121,4914-4915.
[15]Liu J,Alvarrez J,et al.Phase Transfer of Hydrophilic,Cyclodextrin-Modified Gold Nanoparticles to Chloroform Solutions[J].J Am Chem Soc,2001,123,11148.
[16]Petter R C,Salek J S,Sikorski C T,etal.Cooperative binding by aggregatedmono-6-(alkylamino) -beta-cyclodextrins [J].J Am Chem Soc,1990,112,3860-3868.
[17]Fujita K,Ueda T,Imoto T,et al.Guest-induced conformational change ofβ-cyclodextrin capped with an environmentally sensitive chromophore[J].Bioorg Chem,1982,11,72-84.
[18]Liu J,Ong W,Roman E,et al.Cyclodextrin-Modified Gold Nanospheres[J].Langmuir,2000,16,3000-3002.
[19]钱琛.β-环糊精的包和作用及其衍生物在金纳米粒子上的修饰特性研究[D].扬州大学,2005.
[20]Gonzalez Gaitano G,Guerrero Matinez A,Ortega F,et al.Thermodynamic and Spectroscopic Study of a Molecular Rotaxane Containing a Bolaform Surfactant andβ-Cyclodextrin[J].Langmuir,2001,17,1392.
[21]Hostetler M,Wingate J,Murray R.Alkanethiolate Gold Cluster Molecules with Core Diameters from 1.5 to 5.2 nm:Core and Monolayer Properties as a Function of Core Size[J].Langmuir,1998,14,17-30.
[1] Marcucci F,Mussini E,Poy F,et a1.Separation of amino acids as their n-trifluoroacetyl-n-butyl esters by gas chromatography[J].Chromatogr A,1965,8,487-491.
[2] Smith J T.Recent advancements in amino acid analysis using capillary electrophoresis[J]. Electrophoresis,1999,20,3078-3083.
[3] Prata C,Bonnafous P,Fraysse N,et al.Recent advances in amino acid analysis by capillary electrophoresis [J].Electrophoresis,2001,22,4129-4138.
[4] Poinsot V,Bayle C,Couderc F.Recent advances in amino acid analysis by capillary electrophoresis [J].Electrophoresis,2003,24,4047-4062.
[5] Yang L,Zhang D,Yuan Z.Enantioseparation of o-phthaldiadehyde derivatized amino acids using CD-modified micellar eleetrokinetie chromatography in the mixed aqueous-organic media[J].Anal Chem Acta,2001,433,23-30.
[6] Koop D R,Morgan E T,Tarr G E,et al.Purification and characterization of a unique isozyme of cytochrome P-450 from liver microsomes of ethanol-treated rabbits[J].J Biol Chem,1982,257,8472-8480.
[7] Bidlingmeyer B A,Cohen S A,Tarvin T L.Rapid analysis of amino acids using pre- column derivatization [J].J Chromatogr,1984,336(1):93-104.
[8] RU Qinhua,YAO J ia,LUO Guo an,et al.Pressurized gradient capillary electrochromatographic separation of eighteen amino acid derivatives[J].J Chromatogr A,2000,894,337-343.
[9]林红,柯丹如.高效毛细管区带电泳快速测定复方氨基酸注射液中三种氨基酸的含量[J].福建医科大学学报,2002,36,105-106.
[10]刘阳,张颖冬,柯晓燕.毛细管电泳快速测定脑脊液中谷氨酰胺含量[J].临床检验杂志,2002,120(6):352-353.
[11]Shen Z J,Sun Z M,Wu L,et al.Rapid method for the determination of amino acids in serum by capillary electrophoresis[J].J Chromatogr A,2002,979,227-232.
[12]陈惜贞.高效毛细管电泳法快速测定血清中游离氨基酸[J].检验医学与临床,2007,4(6):516-517.
[13]Kang J W,Yang Y T,You J M.Fast chiral separation of amino acid derivatives and acidic drugs by co-electroosmotic flow capillary eleetrophoresis with vancomycin as chiral selector[J].J Chromatogr A,1998,825,81-87.
[14]阮宗琴,李菊白,陆豪杰,等.毛细管电动色谱带电环糊精拆分N-FMOC氨基酸对映体[J].色谱,2000,18(2):148-151.
[15]Chen Fang,Zhang Shufeng,Qi L i,et al.Chiral capillary electrophoretic separation of amino acids derivatized with 9-fluorenylmethylchloroformate using mixed chiral selectors ofβ-cyclodextrin and sodium taurodeoxycholate [J].Electrophoresis,2006,27,2896-2904.
[16]Desiderio G,Fanali S.Use of negatively charged sulfobutyl ether-cyclodextrin for enantiomeric separation by capillary electrophoresis[J].J Chromatogr A,1995,716,183-196.
[17]Hernández-Orte P,Ibarz M J,Cacho J, et al.Amino Acid Determination in Grape Juices and Wines by HPLC Using a Modification of the 6-Aminoquinolyl- N-Hydroxysuccinimidyl Carbamate (AQC) Method[J].Chromatographia,2003,58,29-35.
[18]Diaz J,Lliberia J L,Comellas L,et al.Amino acid and amino sugar determination by derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate followed by high-performance liquid chromatography and fluorescence detection[J].J Chromatogr A,1996,719(1):171-179.
[19]林向成,赵书林.氨基酸和多巴对映体的毛细管电泳手性拆分新体系研究[D].广西师范大学,2004.
[20]李芳,史霄燕.2,4-二硝基氯苯衍生化法在反相高效液相色谱测定氨基酸中的应用研究[J].色谱,1995,13(3):200-202.
[21]Na N,Hu Y P,Ouyang J,et al.Use of polystyrene nanoparticles to enhance enantiomeric separation of propranolol by capillary electrophoresis with Hp-beta-CD as chiral selector[J].Analytica Chimica Acta,2004,527,139-147.
[1]Gassmann E,Kuo J E,Zare R N.Electrokinetic Separation of Chiral Compounds[J].Science,1985,230,813-814.
[2]Fanali S.Identification of chiral drug isomers by capillary electrophoresis[J].J Chromatogr,1996,735,77.
[3]Jeff rey N C,Rene H,J ennifer W,et al.Sedative and anxiolytic effects of Zopielone’s enantiomers and metabolite[J].Eur J Pharm,2001,415,181.
[1]Dicinoski G W,Shellie R A,Haddad P R.Forensic Identification of Inorganic Explosives by Ion Chromatography[J].Anal Lett,2006,39,639.
[2]Hewitt A D,Jenkins T F,Ranney T A.On-site gas chromatographic determination of explosives in soils[J].Field Anal Chem Tech,2001,5,228.
[3]Denekamp C,Tsoglin A.Development of Mass Spectrometric Method for Analysis of Cyclic Nitramine Explosives DTIW and HNIW[J].Anal Chem,2005,77,7796.
[4]Kuila D K,Chakrabortty A,Sharma S P,et a1.Composition profile of low explosives from cases in India[J].Forensic Sci Int,2006,159,127.
[5]Sharma S P,Lahiri S C.Characterization and Identification of Explosives and Explosive Residues Using GC-MS,an FTIR Microscope,and HPTLC[J].J Energ Mater,2005,23,239.
[6]Hilmi A,Luong J H T,Nguyen A L.Development of Electrokinetic Capillary Electrophoresis Equipped with Amperometric Detection for Analysis of Explosive Compounds[J].Anal Chem,1999,71,873.
[7]冯俊鹤,郭宝元,林金明,等.毛细管区带电泳技术快速分离检测爆炸残留物中的无机离子[J].色谱,2008,26(6):667-671.
[8]Northop D M,Martire D E, MacCrehan W A.Separation and identification of organic gunshot and explosive constituents by micellar electrokinetic capillary electrophoresis[J].Anal Chem,1991,63, 1038-1042.
[2] Gross G M,Grate J W,Synovec RE.Monolayer-protected gold nanoparticles as an efficient stationary phase for open tubular gas chromatography using a square capillary model for chip-based gas chromatography in squarecornered microfabricated channels[J].Journal of chromatography A,2004,1029,185.
[3]罗国安,王义明.毛细管电泳的原理及应用第一讲毛细管电泳简介[J].色谱,1995,13(4):254-256.
[4] Walbmehl Y,Jorgenson J W.On-column UV absorption detector for open tubular capillary zone electrophoresis[J].J Chromatogr A,1984,315,135-143.
[5] Mathies R A,Huang X C.Capillary array electrophoresis:an approach to high-speed,high throughput DNA sequencing[J].Nature,1992,359,167-169.
[6]董捷.毛细管电泳在生物分析化学上的应用及进展[J].山东环境,1998,19-20.
[7]黄少平.高效毛细管电泳法在药物分析及体内分析中的应用[J].中华临床医学研究杂志,2006,12(9):1246-1249.
[8]毛煜,徐建明.毛细管电泳技术和应用新进展[J].化学研究与应用,2001,13(1):4-9.
[9] Yan C,Dadoo R,Zare R N,et al.Gradient Elution in Capillary Electrochromatography[J].Anal Chem,1996,68(17):2726-2730.
[10]夏仕文,李树本.酶在光学活性药物合成中的应用[J].合成化学,1996,4(3):201-207.
[11]Laird T.Delelopment chemistry at its best [M].Chem Ind (London),1989,366-367.
[12]继成.我国医药原料和中间体发展动向[J].中国制药信息,1998,14(12):28-31.
[13]肖畴阡,宋光泉.有机化学[M].广州:中山大学出版社,1996,196.
[14]尹国,刘振华,曾姗姗,等.手性异构体拆分方法的研究进展[J].中国药物化学杂志,2001,11(1):57.
[15]姜廷福,陈豪杰,梁冰,等.毛细管电泳分离液相手性药物[J].药物分析杂志,2002,22(3):245-248.
[16]Terabe S,Otsuka K,Nishi H.Separation of enantiomers by capillary electrophoretic techniques[J].J Chromatogr,1994,666,295-319.
[17]陈义.毛细管电泳技术及应用[M].化学工业出版社,2000,103-105.
[18]Tran A D,Blanc T,Leopold E J.Micellar electrokinetic chromatography:methodological and instrumental advances [J].J Chromatogr,1990,516,241.
[19]Lurie I S.Micellar electrokinetic capillary chromatography of the enantiomers of amphetamine,methamphetamine and their hydroxyphenethylamine precursors[J].J Chromatogr,1992,605,269.
[20]Szejtli J.Introduction and General Overview of Cyclodextrin Chemistry[J].Chem Rev,1998,98(5):1743-1754.
[21]Van Eeckhaut A,Michotte Y.Chiral separations by capillary electrophoresis:Recent developments and applications[J].Electrophoresis,2006,27,2880-2895.
[22]Gubitz G,Schmild M G.Chiral separation principles in capillary electrophoresis[J].J Chromatogr A, 1997,792,179-225.
[23]Fanali S.Identification of chiral drug isomers by capillary electrophoresis[J].J Chromatogr A,1996,735,77-121.
[24]Gubltz G , SchmidM G . Recent Progress In Chiral Separation Principles In Capillary Electrophoresis[J].Electrophoresis,2000,21,4112-4135.
[25]Van Eeckhaut A,Deteaevmier M R,J Crommen,et al.Differential effects of organic modifiers on the enantioseparation of dimetindene maleate with carboxymethyl-β-cyclodextrin in capillary Electrophoresis[J].J SeP Sci,2004,27,21-27.
[26]Wang Z Y,Tang Z M,Z H Gu,et al.Enantioseparation of chiral allenic acids by micellar electrokinetic chromatography with cyclodextrins as chiral selector[J].Electrophoresis,2005,26,1001-1006.
[27]杨郁,郭良宏.超分子主体化合物环糊精应用于环境污染物分离分析的研究进展[J].科学通报,2009,54(2):128-137.
[28]刘夺奎,顾振亚,董振礼.环糊精在纺织染整加工中应用的新进展[J].染整技术,2003,25(3):12-15.
[29]刘旭海.中药制备新技术[J].工艺探讨与系统设计,2009,26.
[30]林向成,赵书林.氨基酸和多巴对映体的毛细管电泳手性拆分新体系研究[D].广西师范大学, 2004.
[31]Fanali S.Separation of optical isomers by capillary zone electrophoresis based on host-guest complexation with cyclodextrins[J].J Chromatogr,1989,474,441-446.
[32]Tanaka M,et al.Enantiomeric separation of dansylamino acids by capillary zone electrophoresis based on complexation with cyclodextrins[J].Fresenius J Anal Chem,1992,339,896.
[33]Yamashoji Y,et al.Chiral recognition and enantiomeric separation of alanineβ-naphthylamide by cyclodextrins[J].Anal Chem Acta,1992,268,39.
[34]Schmitt T,Engelhard H.Derivatized cyclodextrins for the separation of enantiomers in capillary electrophoresis[J].HRC,1993,16,525.
[35]Peterson T E,Trowbridge D.Quantitation of l-epinephrine and determination of the d-/l-epinephrine enantionmer ratio in a pharmaceutical formulation by capillary electrophoresis[J].J Chromatogr,1992,603,298.
[36]Peterson T E.Separation of drug stereoisomers by capillary electrophoresis with cyclodextrins[J].J Chromatogy,1993,630,353.
[37]Fanali S,Bocek P.Enantiomer resolution by using capillary zone electrophoresis.Resolution of racemic tryptophan and determination of the enantiomer composition of commercial pharmaceutical epinephrine[J].Electrophoresis,1990,11,757.
[38]Quang C,Khaladi G.Compounds in Capillary Electrophoresis.Using b-cyclodextrin and Tetraalkyl- ammonium Reagents[J].Anal Chem,1993,65,3354.
[39]Quang C,Khalidi G.Direct separation of the enantiomers of -blockers by cyclodextrin-mediated capillary zone electrophoresis[J].HRC,1994,17,99.
[40]Heuermann M,Blaschke G.Chiral separation of basic drugs using cyclodextrins as chiral pseudo- stationary phases in capillary electrophoresis[J].J Chromatogr,1993,648,267.
[41]Nishi H, et al.Chiral separation of drugs using cyclodextrins in capillary zone electrophoresis[J].J Chromatogr,1994,659,449.
[42]Penn S G,et al.Differential binding of tioconazole enantiomers to hydroxypropyl-β-cyclodextrin studied by capillary electrophoresis[J].J Chromatogr,1993,636,149.
[43]Wren S A C,Rowe R C.Theoretical aspects of chiral separation in capillary electrophoresis:III.Application toβ-blockers[J].J Chromatogr A,1993,635,113.
[44]Nielen M W F.Chiral separation of basic drugs using cyclodextrin-modified capillary zone electrophoresis[J].Anal Chem,1993,65,885.
[45]Schutzner W , Fanali S . Enantiomers resolution in capillary zone electrophoresis by using cyclodextrins[J].Electrophoresis,1992,13,687.
[46]Palmarsdottir S,Edholm L E.Capillary zone electrophoresis for separation of drug enantiomers using cyclodextrins as chiral selectors:Influence of experimental parameters on separation[J].J Chromatogr,1994,666,337.
[47]Schneiderman E,Gratz S R,Stalcup A M.Optimization of preparative electrophoretic chiral separation of ritalin enan-tiomers[J].J Pharm Biomed Anal,2002,27(324):639-650.
[48]Awadallah B,Schmidt P C,Holzgrabe U,et al.Quantitation of talinolol and otherβ-CD-blockers by capillary elec-trophoresis for in vitro drug absorption studies[J].Electrophoresis,2003,24(15):2627-2632.
[49]Paias F O,Bondato P S.Enantioselective analysis of hydrox-ymebendazole in plasma by high- performance liquid chro-matography and capillary electrophoresis[J].Electrophoresis,2003,25(15217):1063-1069.
[50]Pham T T H,Schepdael A V,Hauta-aho T,et al.Simultaneous determination of dopa and carbidopa enantiomers by capillary zone electrophoresis[J].Electrophoresis,2003,23(19):3404-3409.
[51]Jabor V A P,Lanchote V L,Bonato P S.Enantioselective analysis of ibuprofen in human plasma by anionic cyclodextrin-modified electrokinetic chromatography [J].Electrophoresis,2003,23(17):3041-3047.
[52]Viberg P,Jornten Karlsson M,Petersson P.Nanoparticles as pseudostationary phase in capillary electrochromatography/ESI-MS[J].Anal Chem,2002,74,4595-4601.
[53]FujimotoY,MuranakaY.Electrokinetic chromatography using nanometer-sized silica particles as the dynamic stationary phase[J].J High Resolut Chromatogr,1997,20,400-402.
[54]Reynold KJ,ColonLA.Submicron sized organo-silica spheres for capillary electrochromatography[J]. J Liq Chromatogr Relat Teehnol,2000,23,161-173.
[55]Luong J H T,BouvretteP,LiuY L,et al.Electrophoretic separation of aniline derivatives using fused silica capillaries coated with acid treated single-walled carbon nanotubes[J].J Chromatogr A,2005,1074,187-194.
[56]Mahony T O , OwensV P , et al . Alkylthiol gold nanparticles in open-tubular capillary eleetrochromatogr-aphy [J].J Chromatogr A,2003,1004,181-193.
[57]Yang L,Guihen E,et al.Gold nanoparticle-modified etched capillary for open-tubular capillary electrochromatography[J].Anal Chem 2005,77,1840-1846.
[58]GrossG M,NelsonD A,Grate J W,etal.Monolayer-protected gold nanoparticles as a stationary phase for open tubular gas chromatography[J].Anal Chem,2003,75,4558-4564.
[1] Frens G.Controlled Nucleation for the Regulation of the Partiele Monodis Perse Gold Suspensions [J].Nature:Phys Sci,1973,241,20-22.
[2] Natan M J,et a1.Morphology-Dependent Electrochemistry of Cytochrome c at Au Colloid-Modified SnO2 Electrodes[J].J Am Chem Soc,1996,118,1154.
[3] Yonezawa T,Sutoh M,Kunitake T.Practieal Preparation of Size-Controlled GoldNano Particles In Water[J].Chem Lett,1997,7,619-620.
[4] Yonezawa T,Kunitake T.Practical Preparationof Anionic Mereapto Ligand-Stabilized Gold Nano- Particles and Their Immobilization[J].Colloids Surf A:Physicochem Eng Aspeets,1999,149,193-199.
[5] Carotenuto G,Nieolais L.Size-controlled sythesis of Thiol-Derivatized Gold Clusters[J].J Mater Chem,2003,13,1038-1041.
[6] Pengo P,Polizzi S,Battagliarin M,et al.Synthes,Characterization and Properties of Water-Soluble Gold Nano Particles withTunable Core Size[J].J Mater Chem,2003,13,2471-2478.
[7] BrownK R,Natan M J.Hydroxylamine Seeding of Colloidal An NanoParticles in Solution and on Surfaces[J].Langmuir,1998,14,726-728.
[8]朱梓华,朱涛,刘忠范.大粒径单分散金纳米粒子的水相合成[J].物理化学报,1999,15,966-970.
[9] SaundersA E,SiglnanM B Jr,KorgelB A.Growth kinetics and Metastability of MonodisPerse Tetraoetylammonium Bromide Capped Gold Nanocrystals[J].J Phys Chem B,2004,108,193-199.
[10]Sayd B,PrashantV K,Surat H.Photoinduced EleetronTransfer between Chlorophylla and Gold Nanoparticles[J].J Phys Chem B,2005,109,16-723.
[11]Jin R,Wu G,Li Z,et al.What Controls the Melting Properties of DNA-Linked Gold NanoParticle Assemblies[J].J Am Chem Soc,2003,125,1643-1654.
[12]Brust M,Walker M,et al.Synthesis of Thiol Derivatised Gold Nanoparticles in a Two Phase Liquid/Liquid System[J].J Chem Soc Chem Commun,1994,7,801.
[13]Fullam S,Rao SN,Fitzmaurice D.Noncovalent Self-Assembly of Silver Nanocrystal Aggregates in Solution[J].J Phys Chem B,2000,104,6164.
[14]Boal A K , Rotello V M . Redox-Modulated Recognition of Flavin by Functionalized Gold Nanoparticles[J].J Am Chem Soc,1999,121,4914-4915.
[15]Liu J,Alvarrez J,et al.Phase Transfer of Hydrophilic,Cyclodextrin-Modified Gold Nanoparticles to Chloroform Solutions[J].J Am Chem Soc,2001,123,11148.
[16]Petter R C,Salek J S,Sikorski C T,etal.Cooperative binding by aggregatedmono-6-(alkylamino) -beta-cyclodextrins [J].J Am Chem Soc,1990,112,3860-3868.
[17]Fujita K,Ueda T,Imoto T,et al.Guest-induced conformational change ofβ-cyclodextrin capped with an environmentally sensitive chromophore[J].Bioorg Chem,1982,11,72-84.
[18]Liu J,Ong W,Roman E,et al.Cyclodextrin-Modified Gold Nanospheres[J].Langmuir,2000,16,3000-3002.
[19]钱琛.β-环糊精的包和作用及其衍生物在金纳米粒子上的修饰特性研究[D].扬州大学,2005.
[20]Gonzalez Gaitano G,Guerrero Matinez A,Ortega F,et al.Thermodynamic and Spectroscopic Study of a Molecular Rotaxane Containing a Bolaform Surfactant andβ-Cyclodextrin[J].Langmuir,2001,17,1392.
[21]Hostetler M,Wingate J,Murray R.Alkanethiolate Gold Cluster Molecules with Core Diameters from 1.5 to 5.2 nm:Core and Monolayer Properties as a Function of Core Size[J].Langmuir,1998,14,17-30.
[1] Marcucci F,Mussini E,Poy F,et a1.Separation of amino acids as their n-trifluoroacetyl-n-butyl esters by gas chromatography[J].Chromatogr A,1965,8,487-491.
[2] Smith J T.Recent advancements in amino acid analysis using capillary electrophoresis[J]. Electrophoresis,1999,20,3078-3083.
[3] Prata C,Bonnafous P,Fraysse N,et al.Recent advances in amino acid analysis by capillary electrophoresis [J].Electrophoresis,2001,22,4129-4138.
[4] Poinsot V,Bayle C,Couderc F.Recent advances in amino acid analysis by capillary electrophoresis [J].Electrophoresis,2003,24,4047-4062.
[5] Yang L,Zhang D,Yuan Z.Enantioseparation of o-phthaldiadehyde derivatized amino acids using CD-modified micellar eleetrokinetie chromatography in the mixed aqueous-organic media[J].Anal Chem Acta,2001,433,23-30.
[6] Koop D R,Morgan E T,Tarr G E,et al.Purification and characterization of a unique isozyme of cytochrome P-450 from liver microsomes of ethanol-treated rabbits[J].J Biol Chem,1982,257,8472-8480.
[7] Bidlingmeyer B A,Cohen S A,Tarvin T L.Rapid analysis of amino acids using pre- column derivatization [J].J Chromatogr,1984,336(1):93-104.
[8] RU Qinhua,YAO J ia,LUO Guo an,et al.Pressurized gradient capillary electrochromatographic separation of eighteen amino acid derivatives[J].J Chromatogr A,2000,894,337-343.
[9]林红,柯丹如.高效毛细管区带电泳快速测定复方氨基酸注射液中三种氨基酸的含量[J].福建医科大学学报,2002,36,105-106.
[10]刘阳,张颖冬,柯晓燕.毛细管电泳快速测定脑脊液中谷氨酰胺含量[J].临床检验杂志,2002,120(6):352-353.
[11]Shen Z J,Sun Z M,Wu L,et al.Rapid method for the determination of amino acids in serum by capillary electrophoresis[J].J Chromatogr A,2002,979,227-232.
[12]陈惜贞.高效毛细管电泳法快速测定血清中游离氨基酸[J].检验医学与临床,2007,4(6):516-517.
[13]Kang J W,Yang Y T,You J M.Fast chiral separation of amino acid derivatives and acidic drugs by co-electroosmotic flow capillary eleetrophoresis with vancomycin as chiral selector[J].J Chromatogr A,1998,825,81-87.
[14]阮宗琴,李菊白,陆豪杰,等.毛细管电动色谱带电环糊精拆分N-FMOC氨基酸对映体[J].色谱,2000,18(2):148-151.
[15]Chen Fang,Zhang Shufeng,Qi L i,et al.Chiral capillary electrophoretic separation of amino acids derivatized with 9-fluorenylmethylchloroformate using mixed chiral selectors ofβ-cyclodextrin and sodium taurodeoxycholate [J].Electrophoresis,2006,27,2896-2904.
[16]Desiderio G,Fanali S.Use of negatively charged sulfobutyl ether-cyclodextrin for enantiomeric separation by capillary electrophoresis[J].J Chromatogr A,1995,716,183-196.
[17]Hernández-Orte P,Ibarz M J,Cacho J, et al.Amino Acid Determination in Grape Juices and Wines by HPLC Using a Modification of the 6-Aminoquinolyl- N-Hydroxysuccinimidyl Carbamate (AQC) Method[J].Chromatographia,2003,58,29-35.
[18]Diaz J,Lliberia J L,Comellas L,et al.Amino acid and amino sugar determination by derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate followed by high-performance liquid chromatography and fluorescence detection[J].J Chromatogr A,1996,719(1):171-179.
[19]林向成,赵书林.氨基酸和多巴对映体的毛细管电泳手性拆分新体系研究[D].广西师范大学,2004.
[20]李芳,史霄燕.2,4-二硝基氯苯衍生化法在反相高效液相色谱测定氨基酸中的应用研究[J].色谱,1995,13(3):200-202.
[21]Na N,Hu Y P,Ouyang J,et al.Use of polystyrene nanoparticles to enhance enantiomeric separation of propranolol by capillary electrophoresis with Hp-beta-CD as chiral selector[J].Analytica Chimica Acta,2004,527,139-147.
[1]Gassmann E,Kuo J E,Zare R N.Electrokinetic Separation of Chiral Compounds[J].Science,1985,230,813-814.
[2]Fanali S.Identification of chiral drug isomers by capillary electrophoresis[J].J Chromatogr,1996,735,77.
[3]Jeff rey N C,Rene H,J ennifer W,et al.Sedative and anxiolytic effects of Zopielone’s enantiomers and metabolite[J].Eur J Pharm,2001,415,181.
[1]Dicinoski G W,Shellie R A,Haddad P R.Forensic Identification of Inorganic Explosives by Ion Chromatography[J].Anal Lett,2006,39,639.
[2]Hewitt A D,Jenkins T F,Ranney T A.On-site gas chromatographic determination of explosives in soils[J].Field Anal Chem Tech,2001,5,228.
[3]Denekamp C,Tsoglin A.Development of Mass Spectrometric Method for Analysis of Cyclic Nitramine Explosives DTIW and HNIW[J].Anal Chem,2005,77,7796.
[4]Kuila D K,Chakrabortty A,Sharma S P,et a1.Composition profile of low explosives from cases in India[J].Forensic Sci Int,2006,159,127.
[5]Sharma S P,Lahiri S C.Characterization and Identification of Explosives and Explosive Residues Using GC-MS,an FTIR Microscope,and HPTLC[J].J Energ Mater,2005,23,239.
[6]Hilmi A,Luong J H T,Nguyen A L.Development of Electrokinetic Capillary Electrophoresis Equipped with Amperometric Detection for Analysis of Explosive Compounds[J].Anal Chem,1999,71,873.
[7]冯俊鹤,郭宝元,林金明,等.毛细管区带电泳技术快速分离检测爆炸残留物中的无机离子[J].色谱,2008,26(6):667-671.
[8]Northop D M,Martire D E, MacCrehan W A.Separation and identification of organic gunshot and explosive constituents by micellar electrokinetic capillary electrophoresis[J].Anal Chem,1991,63, 1038-1042.