HPLC手性流动相添加剂及其用于药物对映体拆分中的影响因素
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摘要
高效液相色谱手性流动相添加剂法是拆分药物对映体的方法之一。它不需要使用手性柱也能高效分离药物对映体,且具有操作简便、应用范围广和通用性好等特点。本文综述了手性流动相添加剂的种类,其拆分药物对映体的原理及在拆分过程中的影响因素,对药物对映体的拆分具有重要指导意义。
The chiral mobile phase additives method in High performance liquid chromatography(HPLC) is one of the methods of resolving drug enantiomers. This method does not require the use of chiral column, can efficiently separate the drug enantiomers, and has the advantages of simple operation, wide application and universality. This paper summarizes the types of chiral mobile phase additives, the principle of using it to the resolution of drug enantiomers and their influencing factors in the application of resolution, which are of great significance to the resolution of the drug enantiomers.
The chiral mobile phase additives method in High performance liquid chromatography(HPLC) is one of the methods of resolving drug enantiomers. This method does not require the use of chiral column, can efficiently separate the drug enantiomers, and has the advantages of simple operation, wide application and universality. This paper summarizes the types of chiral mobile phase additives, the principle of using it to the resolution of drug enantiomers and their influencing factors in the application of resolution, which are of great significance to the resolution of the drug enantiomers.
引文
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[3]刘育坚,刘智敏,许志刚.萘普生对映体的拆分及其手性药物的测定[J].化学研究与应用,2017,29(1):137-141.
[4]Jiao F P,Huang K L,Ning F R,et al.Chromatographic Separation of Naproxen Enantiomers using Hydroxypropyl-β-Cyclodextrin as Chiral Mobile Phase Additive[J].Separation Science and Technology,2006,41(9):1893-1906.
[5]全思思,陈智,吴学昊,等.3种含氮杂环类药物的手性色谱拆分及其制剂中对映体含量的测定[J].分析测试学报,2016,35(9):1167-1171.
[6]Patel B K,Hanna-brown M,Hadley M R,et al.Enantiomeric Resolution of 2-Arylpropionic Acid Nonsteroidal Anti-inflammatory Drugs by Capillary Electrophoresis:Methods and Applications[J].Elec trophoresis,2004,25(16):2625-2656.
[7]Bhavyasri K,Rambabu D,Prasad PSS,et al.Separation of Enantiomers of Clopidogrel on Chiral Stationary Phases by Packed Column Supercritical Fluid Chromatography[J].American Journal of Analytical Chemistry,2013,4(1):51-55.
[8]陈卓铃,丁国生.聚乙烯亚胺键合涂层毛细管用于改善碱性药物的对映体拆分[J].色谱,2006,24(6):658-658.
[9]Bounoua N,Sekkoum K,Belboukhari N,et al.Achiral and Chiral Separation and Analysis of Antifungal Drugs by HPLC and CE:AComparative Study:Mini Review[J].Journal of Liquid Chromatography&Related Technologies,2016,39(11):513-519.
[10]Chavan M,Sutar M,Deshmukh S.Significance of Various Chromatographic Techniques in Drug Discovery and Development[J].Int J Res Pharmacy Chem,2013,3(2):282-289.
[11]聂桂珍,李来生,程彪平,等.磺丁基醚-β-环糊精修饰毛细管电色谱拆分地平类药物对映体[J].高等学校化学学报,2014,35(7):1414-1422.
[12]罗安,万强,范华均,等.纤维素-三(4-甲基苯甲酸酯)手性固定相拆分5种芳基丙酸类药物对映体及其制剂的含量测定[J].色谱,2014,32(9):1013-1018.
[13]胡艳丽,赵旻,郭雯雯,等.羧甲基-β-环糊精为手性选择剂拆分盐酸尼卡地平等6种药物对映体[J].沈阳药科大学学报,2013,30(2):114-119.
[14]刘静,袁晓薇,马郑,等.羧甲基-β-环糊精为手性选择剂拆分托吡卡胺等4种手性药物对映体[J].沈阳药科大学学报,2013,30(5):374-378.
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[16]Listed N.FDA'S Policy Statement for the Development of New Stereoisomeric Drugs[J].Chirality,2010,4(5):338-340.
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[18]董淑波,杨汉跃,陈学民,等.高效液相色谱法拆分阿雷地平对映异构体[J].药物分析杂志,2017,37(6):1113-1116.
[19]王舒,韦思平,王力,等.高效液相色谱法手性拆分(2-戊基-3-苯基-2,3环氧丙烷基)二苯基磷酸酯对映体[J].分析科学学报,2017,33(2):237-241.
[20]王芳,张莹,颜冬云,等.拟除虫菊酯气相色谱手性拆分方法及其影响因素分析[J].环境科学与技术,2012,35(9):82-85.
[21]左莉华,孙志,郭兴杰,等.高效毛细管电泳法拆分5种手性药物[J].中国医院药学杂志,2016,36(12):983-988.
[22]陈香玲,李丽.超临界流体色谱法手性拆分盐酸罗哌卡因及其右旋异构体[J].天津药学,2017,29(3):4-7.
[23]Brondz I,Brondz A.Review:Isomer Separation,Chiral Resolution,and Structure Elucidation Analyses Are the Future of Analytical Supercritical Fluid Chromatography-Mass Spectrometry[J].International Journal of Analytical Mass Spectrometry&Chromatograp hy,2014,61(2):15-24.
[24]Dorsey JG,Cooper WT.Liquid Chromatography Theory and Methodology[J].Analytical Chemistry,1998,70(12):59l-691.
[25]Ward TJ,Ward KD.Chiral Separations:Fundamental Review 20l0[J].Analytical Chemistry,2010,82(12):4712-4722.
[26]Cavazzini A,Pasti L,Massi A,et al.Recent Applications in Chiral High Performance Liquid Chromatography:a Review[J].Analytica Chimica Acta,2011,706(2):205-222.
[27]Beesley TE,Lee JT,Wang AX.Method Development and Optimization of Enantiomeric Separations using Macrocyclic Glycopeptide Chiral Stationary Phases[M].Second Edition.Chiral Separation Techniques:A Practical Approach,2001:25-54.
[28]Peng Y,He Q S,Cai J,et al.Enantioseparation of Citalopram by RP-HPLC,Using Sulfobutyl Ether-β-Cyclodextrin as a Chiral Mobile Phase Additive[J].International Journal of Analytical Chemistry,2016(3):1231386.
[29]Xie J,Tan Q,Yang L,et al.A Simple and Rapid Method for Chiral Separation of Amlodipine using Dual Chiral Mobile Phase Additives[J].Analytical Methods,2014,6(12):4408-4413.
[30]Tong S,Zhang H,Shen M,et al.Enantioseparation of Mandelic Acid Derivatives by High Performance Liquid Chromatography with Substitutedβ-Cyclodextrin as Chiral Mobile Phase Additive and Evaluation of Inclusion Complex Formation[J].Journal of Chromatography B,2014,962:44-51.
[31]翟明翚,苏立强,王颖,等.HPLC手性流动相添加剂法拆分盐酸地匹福林对映体[J].化学试剂,2013,35(6):555-557.
[32]Yin Y,Qiao L,Zhang Q.HPLC Determination of Tirofiban using Chiral Mobile Phase[J].Chinese Journal of Pharmaceutical Analysis,2013,33(6):1012-1015.
[33]翟明翚,苏立强,王颖,等.HPLC手性流动相添加剂法拆分美索巴莫对映体[J].化学研究与应用,2016,28(3):416-419.
[34]叶祥喜,宋燕西,陈旭涛,等.高效液相色谱手性流动相添加剂法拆分佐匹克隆对映体[J].分析测试学报,2014,33(4):471-474.
[35]Deshpande K,Pillai M,Joshi V,et al.Chiral Separation of Citalopram by Reversed Phase HPLC using Sulfated Beta Cyclodextrin as Chiral Mobile Phase Additive[J].International Journal of Pharmacy&Pharmaceutical Sciences,2015,7(6):306-310.
[36]张虎,沈芒芒,童胜强,等.高效液相色谱手性流动相添加法拆分阿卓乳酸对映体[J].色谱,2014,32(6):612-615.
[37]刘静,董斌,丁红雨.以羧甲基-β-环糊精为HPLC手性流动相添加剂法分离两种手性药物对映体[J].中国药物评价,2014,31(3):134-137.
[38]翟明翚,苏立强,王颖,等.羧甲基-β-环糊精手性流动相添加剂法分离盐酸去甲苯福林对映体[J].化工时刊,2016,30(10):1-3.
[39]周文丽,黄璞,任秀华.高效液相色谱法同时测定莫西沙星及其对映体的含量[J].中国医院药学杂志,2014,34(8):652-655.
[40]Liang X,Zhao L,Deng M,et al.Separation of Ofloxacin and Its Six Related Substances Enantiomers by Chiral Ligand-Exchange Chromatography[J].Chirality,2015,27(11):843-849.
[41]Sa?dat B,Boudah F,Guermouche MH.High Performance Liquid Chromatography Chiral Separation of D,l-Phenylalanine and D,l-Tryptophan with Quaternary Mobile Phase Mixture by Copper Mixed Chelate Complexation[J].Analele Universitatii din Bucuresti:Chimie,2010,19(2):77-82.
[42]王金朝,曾苏.高效液相色谱手性流动相添加剂法分离扁桃酸和邻氯扁桃酸对映体[J].分析化学,2005,33(7):1050.
[43]杨座国,杨远明,许振良.手性流动相高效液相色谱法拆分D,L-色氨酸[J].华东理工大学学报(自然科学版),2005,31(1):1-4.
[44]Zhang Z,Yang G,Wang D,et al.Chiral Separation and Enantiomeric Purity Determination of Pazufloxacin Mesilate by HPLC Using Chiral Mobile Phase Additives[J].Journal of Liquid Chromatography&Related Technologies,2004,27(5):813-827.
[45]王荣,谢景文,贾正平,等.高效液相色谱手性流动相拆分甲状腺素对映体[J].分析化学,2001,29(4):406-409.
[46]李乃瑄,阎秀芳,肖如亭.HPLC手性离子对试剂法拆分普萘洛尔对映体[J].应用化工,2003,32(2):48-50.
[47]徐秀珠,邹莉,胡明华,等.离子对色谱法分离氨基醇类对映体[J].分析化学,2001,29(11):1295-1298.
[48]Pettersson C,Gioeli C.Chiral Separation of Amines using ReversedPhased Ion-Pair Chromatography[J].Chirality,1993,5(4):241-245.
[49]谢升谷,郑国钢,陶巧凤,等.HPLC手性流动相添加剂法测定左旋多巴与左旋多巴片中异构体含量[J].海峡药业,2015,27(2):54-56.
[50]Gyllenhaal O,Karlsson A.Enantiomeric Separations of Amino Alcohols by Packed-Column SFC on Hypercarb with l-(+)-tartaric Acid as Chiral Selector[J].Journal of biochemical and biophysical methods,2002,54(1-3):169-185.
[51]Pettersson C.Liquid Chromatographic Separation of Enantiomers using Chiral Additives in the Mobile Phase[J].TrAC Trends in Analytical Chemistry,1988,7(6):209-217.
[2]Hillier M C,Reider P J.Stereoselective Synthesis from a Process Research Perspective[J].Drug Discovery Today,2002,7(5):303-314.
[3]刘育坚,刘智敏,许志刚.萘普生对映体的拆分及其手性药物的测定[J].化学研究与应用,2017,29(1):137-141.
[4]Jiao F P,Huang K L,Ning F R,et al.Chromatographic Separation of Naproxen Enantiomers using Hydroxypropyl-β-Cyclodextrin as Chiral Mobile Phase Additive[J].Separation Science and Technology,2006,41(9):1893-1906.
[5]全思思,陈智,吴学昊,等.3种含氮杂环类药物的手性色谱拆分及其制剂中对映体含量的测定[J].分析测试学报,2016,35(9):1167-1171.
[6]Patel B K,Hanna-brown M,Hadley M R,et al.Enantiomeric Resolution of 2-Arylpropionic Acid Nonsteroidal Anti-inflammatory Drugs by Capillary Electrophoresis:Methods and Applications[J].Elec trophoresis,2004,25(16):2625-2656.
[7]Bhavyasri K,Rambabu D,Prasad PSS,et al.Separation of Enantiomers of Clopidogrel on Chiral Stationary Phases by Packed Column Supercritical Fluid Chromatography[J].American Journal of Analytical Chemistry,2013,4(1):51-55.
[8]陈卓铃,丁国生.聚乙烯亚胺键合涂层毛细管用于改善碱性药物的对映体拆分[J].色谱,2006,24(6):658-658.
[9]Bounoua N,Sekkoum K,Belboukhari N,et al.Achiral and Chiral Separation and Analysis of Antifungal Drugs by HPLC and CE:AComparative Study:Mini Review[J].Journal of Liquid Chromatography&Related Technologies,2016,39(11):513-519.
[10]Chavan M,Sutar M,Deshmukh S.Significance of Various Chromatographic Techniques in Drug Discovery and Development[J].Int J Res Pharmacy Chem,2013,3(2):282-289.
[11]聂桂珍,李来生,程彪平,等.磺丁基醚-β-环糊精修饰毛细管电色谱拆分地平类药物对映体[J].高等学校化学学报,2014,35(7):1414-1422.
[12]罗安,万强,范华均,等.纤维素-三(4-甲基苯甲酸酯)手性固定相拆分5种芳基丙酸类药物对映体及其制剂的含量测定[J].色谱,2014,32(9):1013-1018.
[13]胡艳丽,赵旻,郭雯雯,等.羧甲基-β-环糊精为手性选择剂拆分盐酸尼卡地平等6种药物对映体[J].沈阳药科大学学报,2013,30(2):114-119.
[14]刘静,袁晓薇,马郑,等.羧甲基-β-环糊精为手性选择剂拆分托吡卡胺等4种手性药物对映体[J].沈阳药科大学学报,2013,30(5):374-378.
[15]Rentsch K M.The Importance of Stereoselective Determination of Drugs in the Clinical Laboratory[J].Journal of Biochemical and biophysical Methods,2002,54(1-3):1-9.
[16]Listed N.FDA'S Policy Statement for the Development of New Stereoisomeric Drugs[J].Chirality,2010,4(5):338-340.
[17]Lu H.Stereoselectivity in Drug Metabolism[J].Expert Opinion on Drug Metabolism&Toxicology,2007,3(2):149-158.
[18]董淑波,杨汉跃,陈学民,等.高效液相色谱法拆分阿雷地平对映异构体[J].药物分析杂志,2017,37(6):1113-1116.
[19]王舒,韦思平,王力,等.高效液相色谱法手性拆分(2-戊基-3-苯基-2,3环氧丙烷基)二苯基磷酸酯对映体[J].分析科学学报,2017,33(2):237-241.
[20]王芳,张莹,颜冬云,等.拟除虫菊酯气相色谱手性拆分方法及其影响因素分析[J].环境科学与技术,2012,35(9):82-85.
[21]左莉华,孙志,郭兴杰,等.高效毛细管电泳法拆分5种手性药物[J].中国医院药学杂志,2016,36(12):983-988.
[22]陈香玲,李丽.超临界流体色谱法手性拆分盐酸罗哌卡因及其右旋异构体[J].天津药学,2017,29(3):4-7.
[23]Brondz I,Brondz A.Review:Isomer Separation,Chiral Resolution,and Structure Elucidation Analyses Are the Future of Analytical Supercritical Fluid Chromatography-Mass Spectrometry[J].International Journal of Analytical Mass Spectrometry&Chromatograp hy,2014,61(2):15-24.
[24]Dorsey JG,Cooper WT.Liquid Chromatography Theory and Methodology[J].Analytical Chemistry,1998,70(12):59l-691.
[25]Ward TJ,Ward KD.Chiral Separations:Fundamental Review 20l0[J].Analytical Chemistry,2010,82(12):4712-4722.
[26]Cavazzini A,Pasti L,Massi A,et al.Recent Applications in Chiral High Performance Liquid Chromatography:a Review[J].Analytica Chimica Acta,2011,706(2):205-222.
[27]Beesley TE,Lee JT,Wang AX.Method Development and Optimization of Enantiomeric Separations using Macrocyclic Glycopeptide Chiral Stationary Phases[M].Second Edition.Chiral Separation Techniques:A Practical Approach,2001:25-54.
[28]Peng Y,He Q S,Cai J,et al.Enantioseparation of Citalopram by RP-HPLC,Using Sulfobutyl Ether-β-Cyclodextrin as a Chiral Mobile Phase Additive[J].International Journal of Analytical Chemistry,2016(3):1231386.
[29]Xie J,Tan Q,Yang L,et al.A Simple and Rapid Method for Chiral Separation of Amlodipine using Dual Chiral Mobile Phase Additives[J].Analytical Methods,2014,6(12):4408-4413.
[30]Tong S,Zhang H,Shen M,et al.Enantioseparation of Mandelic Acid Derivatives by High Performance Liquid Chromatography with Substitutedβ-Cyclodextrin as Chiral Mobile Phase Additive and Evaluation of Inclusion Complex Formation[J].Journal of Chromatography B,2014,962:44-51.
[31]翟明翚,苏立强,王颖,等.HPLC手性流动相添加剂法拆分盐酸地匹福林对映体[J].化学试剂,2013,35(6):555-557.
[32]Yin Y,Qiao L,Zhang Q.HPLC Determination of Tirofiban using Chiral Mobile Phase[J].Chinese Journal of Pharmaceutical Analysis,2013,33(6):1012-1015.
[33]翟明翚,苏立强,王颖,等.HPLC手性流动相添加剂法拆分美索巴莫对映体[J].化学研究与应用,2016,28(3):416-419.
[34]叶祥喜,宋燕西,陈旭涛,等.高效液相色谱手性流动相添加剂法拆分佐匹克隆对映体[J].分析测试学报,2014,33(4):471-474.
[35]Deshpande K,Pillai M,Joshi V,et al.Chiral Separation of Citalopram by Reversed Phase HPLC using Sulfated Beta Cyclodextrin as Chiral Mobile Phase Additive[J].International Journal of Pharmacy&Pharmaceutical Sciences,2015,7(6):306-310.
[36]张虎,沈芒芒,童胜强,等.高效液相色谱手性流动相添加法拆分阿卓乳酸对映体[J].色谱,2014,32(6):612-615.
[37]刘静,董斌,丁红雨.以羧甲基-β-环糊精为HPLC手性流动相添加剂法分离两种手性药物对映体[J].中国药物评价,2014,31(3):134-137.
[38]翟明翚,苏立强,王颖,等.羧甲基-β-环糊精手性流动相添加剂法分离盐酸去甲苯福林对映体[J].化工时刊,2016,30(10):1-3.
[39]周文丽,黄璞,任秀华.高效液相色谱法同时测定莫西沙星及其对映体的含量[J].中国医院药学杂志,2014,34(8):652-655.
[40]Liang X,Zhao L,Deng M,et al.Separation of Ofloxacin and Its Six Related Substances Enantiomers by Chiral Ligand-Exchange Chromatography[J].Chirality,2015,27(11):843-849.
[41]Sa?dat B,Boudah F,Guermouche MH.High Performance Liquid Chromatography Chiral Separation of D,l-Phenylalanine and D,l-Tryptophan with Quaternary Mobile Phase Mixture by Copper Mixed Chelate Complexation[J].Analele Universitatii din Bucuresti:Chimie,2010,19(2):77-82.
[42]王金朝,曾苏.高效液相色谱手性流动相添加剂法分离扁桃酸和邻氯扁桃酸对映体[J].分析化学,2005,33(7):1050.
[43]杨座国,杨远明,许振良.手性流动相高效液相色谱法拆分D,L-色氨酸[J].华东理工大学学报(自然科学版),2005,31(1):1-4.
[44]Zhang Z,Yang G,Wang D,et al.Chiral Separation and Enantiomeric Purity Determination of Pazufloxacin Mesilate by HPLC Using Chiral Mobile Phase Additives[J].Journal of Liquid Chromatography&Related Technologies,2004,27(5):813-827.
[45]王荣,谢景文,贾正平,等.高效液相色谱手性流动相拆分甲状腺素对映体[J].分析化学,2001,29(4):406-409.
[46]李乃瑄,阎秀芳,肖如亭.HPLC手性离子对试剂法拆分普萘洛尔对映体[J].应用化工,2003,32(2):48-50.
[47]徐秀珠,邹莉,胡明华,等.离子对色谱法分离氨基醇类对映体[J].分析化学,2001,29(11):1295-1298.
[48]Pettersson C,Gioeli C.Chiral Separation of Amines using ReversedPhased Ion-Pair Chromatography[J].Chirality,1993,5(4):241-245.
[49]谢升谷,郑国钢,陶巧凤,等.HPLC手性流动相添加剂法测定左旋多巴与左旋多巴片中异构体含量[J].海峡药业,2015,27(2):54-56.
[50]Gyllenhaal O,Karlsson A.Enantiomeric Separations of Amino Alcohols by Packed-Column SFC on Hypercarb with l-(+)-tartaric Acid as Chiral Selector[J].Journal of biochemical and biophysical methods,2002,54(1-3):169-185.
[51]Pettersson C.Liquid Chromatographic Separation of Enantiomers using Chiral Additives in the Mobile Phase[J].TrAC Trends in Analytical Chemistry,1988,7(6):209-217.