超临界流体色谱法在手性药物分离中的应用
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摘要
<正>手性是指化学分子的实物与其镜像不能重叠的现象,在自然界中普遍存在。在某些情况下,手性化合物中不同异构体的活性、毒性、代谢可能会存在差别,因此需要对异构体进行分离,并对杂质异构体的含量进行限定以保证药品的安全性、有效性。随着对手性异构体在体内活性差异的认知,以及手性药物上市数量的增多,人们对手性分离技术的需求愈发迫切。目前可应用于手性分离的技术有高效液相色谱法
引文
[1]Klesper E,Corwin AH,Turner DA.High pressure gas chromatography above critical temperatures.J Org Chem,1962,27:700-701.
[2]Saito M.History of supercritical fluid chromatography:instrumental development.J Bioscie Bioeng,2013,115(6):590-599.
[3]Guiochon G,Tarafder A.Fundamental challenges and opportunities for preparative supercritical fluid chromatography.J Chromatogr A,2011,1218(8):1037-1114.
[4]Poling BE,Prausnitz JM,O'Connell JP.The properties of gases and liquids.5th Ed.New York:McGraw-Hill,2001.
[5]De Klerck K,Mangelings D,Vander Heyden Y.Supercritical fluid chromatography for the enantioseparation of pharmaceuticals.J Pharm Biomed Anal,2012,69:77-92.
[6]Bartle KD.Theory and principles of supercritical fluid chromatography//Smith RM.Supercritical fluid chromatography.Loughborough,UK:The Royal Society of Chemistry,1988:1-28.
[7]Ghinet A,Zehani Y,Lipka E.Supercritical fluid chromatography approach for a sustainable manufacture of new stereoisomeric anticancer agent.J Pharm Biomed Anal,2017,145:845-853.
[8]Desfontaine V,Guillarme D,Francotte E,et al.Supercritical fluid chromatography in pharmaceutical analysis.J Pharm Biomed Anal,2015,113:56-71.
[9]Wang RQ,Ong TT,Ng SC,et al.Recent advances in pharmaceutical separations with supercritical fluid chromatography using chiral stationary phases.Trends Anal Chem,2012,37:83-100.
[10]Zhao Y,Woo G,Thomas S,et al.Rapid method development for chiral separation in drug discovery using sample pooling and supercritical fluid chromatography-mass spectrometry.J Chromatogr A,2003,1003(1-2):157-166.
[11]Zou W,Dorsey JG,Chester TL.Modifier effects on column efficiency in packed-column supercritical luid chromatography.Anal Chem,2000,72(15):3620-3626.
[12]Kalíková K,Slechtová T,Vozka J,et al.Supercritical fluid chromatography as a tool for enantioselective separation;a review.Anal Chim Acta,2014,821:1-33.
[13]Salvador A,Herbreteau B,Dreux M,et al.Chiral supercritical fluid chromatography on porous graphitic carbon using commercial dimethyl beta-cyclodextrins as mobile phase additive.J Chromatogr A,2001,929(1-2):101-112.
[14]Speybrouck D,Doublet C,Cardinael P,et al.The effect of high concentration additive on chiral separations in supercritical fluid chromatography.J Chromatogr A,2017,1510:89-99.
[15]Vander Heyden Y,Mangelings D,Matthijs N,et al.Chiral separations//Ahuja S,Dong M.Handbook of pharmaceutical analysis by HPLC.Oxfrod,UK:Academic Press,2005:447-498.
[16]Chen H,Lv XY,Huang JM,et al.Investigation of retention and chiral recognition mechanism of the derivativeβ-cyclodextrin bonded stationary phase.Chem J Chin Univ,2000,21(4):562-565.(in Chinese)陈慧,吕宪禹,黄君珉,等.衍生化环糊精键合固定相色谱保留和手性识别机理的研究(I).高等学校化学学报,2000,21(4):562-565.
[17]Li X,Li YX,Zhang Y.Recent advances in enantio separating chiral drugs by CSP of HPLC.Appl Chem Ind,2014,43(6):1125-1127,1132.(in Chinese)李雪,李优鑫,张勇.高效液相色谱法手性固定相拆分手性药物研究进展.应用化工,2014,43(6):1125-1127,1132.
[18]Berthod A.Chiral recognition in separation methods--mechanisms and applications.Lyon,France:Springer,2010:1-31.
[19]Ikai T,Okamoto Y.Structure control of polysaccharide derivatives for efficient separation of enantiomers by chromatography.Chem Rev,2009,109(11):6077-6101.
[20]Lou X,Janssen HG,Cramers CA.Temperature and pressure effects on solubility in supercritical carbon dioxide and retention in supercritical fluid chromatography.J Chromatogr A,1997,785(1-2):57-64.
[21]?sberg D,Enmark M,Samuelsson J,et al.Evaluation of co-solvent fraction,pressure and temperature effects in analytical and preparative supercritical fluid chromatography.J Chromatogr A,2014,1374:254-260.
[22]Segawa H,Iwata YT,Yamamuro T,et al.Enantioseparation of methamphetamine by supercritical fluid chromatography with cellulose-based packed column.Forensic Sci Int,2017,273:39-44.
[23]Li L.Direct enantiomer determination of methorphan by HPLC-MSand SFC-MS.Forensic Chemi,2016,2:82-85.
[24]Berger TA,Berger BK.Chromatographic resolution of 7 of 8stereoisomers of vitamin K1 on an amylose stationary phase using supercritical fluid chromatography.Chromatographia,2013,76:549-552.
[25]Yang JF,Xu CL,Zhang J,et al.Determination of the enantiomer of iopmamidol by supercritical fluid chromatography.Chin J Mod Appl Pharm,2016,33(12):1566-1569.(in Chinese)杨杰峰,徐川龙,张洁,等.超临界流体色谱法测定碘帕醇的对映异构体.中国现代应用药学,2016,33(12):1566-1569.
[26]Jin W,Yang XL,Lu D,et al.Chiral separation of levetiracetam and R-enantiomer by supercritical fluid chromatography.Chin J Pharm Anal,2013,33(5):822-826.(in Chinese)金薇,杨新磊,陆丹,等.超临界流体色谱法手性拆分左乙拉西坦及其右旋异构体.药物分析杂志,2013,33(5):822-826.
[27]Chen XL,Li L.Chiral separation and determination of ropivacaine hydrochloride and dextroisomer in ropivacaine hydrochloride injection by SFC.Tianjin Pharm,2017,29(3):4-7.(in Chinese)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.天津药学,2017,29(3):4-7.
[28]Dai HX,Yang X,Lin CM.Enantioseparation of 1,4-dihydropyridines calcium antagonistsby supercritical fluid chromatography.Chin J Pharm Anal,2017,37(8):1513-1519.(in Chinese)戴慧雪,杨雪,林春绵.1,4-二氢吡啶类钙拮抗剂在超临界色谱中的对映体分离.药物分析杂志,2017,37(8):1513-1519.
[29]Chen WZ,Xu PX,Yi RZ,et al.Separation of phenylalanine methylester 5’-phosphoamidates of d4t diastereoisomers by supercritical fluid chromatography.Chin J Anal Chem,2012,40(8):1159-1163.(in Chinese)陈伟珠,许鹏翔,易瑞灶,等.超临界流体色谱法分析非对映异构体d4T-5’-N-磷酰化苯丙氨酸甲酯.分析化学研究报告,2012,40(8):1159-1163.
[30]Jin W,Lin H,Chen Y,et al.Chiral separation of ezetimibe and R-enantiomer by supercritical fluid chromatography.Chin Pharm J,2015,50(1):68-71.(in Chinese)金薇,林华,陈阳,等.依折麦布及其R-对映体的超临界流体色谱手性拆分方法研究.中国药学杂志,2015,50(1):68-71.
[31]Dai T,Huang JJ,Ji H,et al.Enantiomers separation of zileuton by supercritical fluid chromatography.West China J Pharm Sci,2012,27(1):67-69.(in Chinese)戴涛,黄珺珺,季红,等.超临界流体色谱拆分齐留通对映体.华西药学杂志,2012,27(1):67-69.
[32]Luo YH.Chiral separation of naproxen enantiomers by supercritical fluid chromatography.China Pharm,2015,26(24):4789-4791.(in Chinese)罗英豪.超临界流体色谱法拆分萘普生对映体.中国药房,2015,26(24):4789-4791.
[33]Toribio L,del Nozal MJ,Bernal JL,et al.Enantiomeric resolution of bifonazole by supercritical fluid chromatography.J Sep Sci,2015,29(10):1373-1378.
[34]Bao Z,Su B,Xing H,et al.Enantioseparation of racemic paroxol on an amylose-based chiral stationary phase by supercritical fluid chromatography.J Sep Sci,2015,33(20):3256-3262.
[35]Li DY,Wu X,Hao FL,et al.Separation of enantiomers by supercritical fluid chromatography on polysaccharide derivative-based chiral stationary phase.Chin J Chromatogr,2016,34(1):80-84.(in Chinese)李冬艳,吴锡,郝芳丽,等.多糖类手性固定相超临界流体色谱法分离手性化合物.色谱,2016,34(1):80-84.
[36]West C,Konjaria ML,Shashviashvili N,et al.Enantioseparation of novel chiral sulfoxides on chlorinated polysaccharide stationary phases in supercritical fluid chromatography.J Chromatogr A,2017,1499:174-182.
[37]Pokrovskiy OI,Ustinovich KB,Usovich OI,et al.A case of Z/E-isomers elution order inversion caused by cosolvent percentage change in supercritical fluid chromatography.J Chromatogr A,2017,1479:177-184.
[38]KalíkováK,MartínkováM,Schmid MG,et al.Cellulose tris-(3,5-dimethylphenylcarbamate)-based chiral stationary phase for the enantioseparation of drugs in supercritical fluid chromatography:comparison with HPLC.J Sep Sci,2018,41(6):1471-1478.
[39]Yu LJ,Huang HW,Li XM,et al.Determination of stereoisomers in landiolol hydrochloride by ultra performance convergence chromatography.Chin J Anal Chem,2016,44(9):1348-1353.(in Chinese)庾莉菊,黄海伟,李秀梅,等.超高效合相色谱法测定盐酸兰地洛尔中立体异构体的含量.分析化学,2016,44(9):1348-1353.
[40]Li SM,Lu YH,Gao L,et al.Study on the separation of cadotril enantiomers with ultra performance convergence chromatography.Chin J Anal Lab,2018,37(4):441-444.(in Chinese)李士敏,陆永辉,高莉,等.超高效合相色谱法拆分卡多曲对映体研究.分析试验室,2018,37(4):441-444.
[41]Wang B,Yan H,Wang SJ,et al.Separation of linalool enantiomer with ultra performance convergence chromatography and thermodynamic studies.J Instrumental Anal,2015,34(7):824-828.(in Chinese)王波,闫衡,王肃军,等.超高效合相色谱对芳樟醇对映体的拆分及热力学研究.分析测试学报,2015,34(7):824-828.
[2]Saito M.History of supercritical fluid chromatography:instrumental development.J Bioscie Bioeng,2013,115(6):590-599.
[3]Guiochon G,Tarafder A.Fundamental challenges and opportunities for preparative supercritical fluid chromatography.J Chromatogr A,2011,1218(8):1037-1114.
[4]Poling BE,Prausnitz JM,O'Connell JP.The properties of gases and liquids.5th Ed.New York:McGraw-Hill,2001.
[5]De Klerck K,Mangelings D,Vander Heyden Y.Supercritical fluid chromatography for the enantioseparation of pharmaceuticals.J Pharm Biomed Anal,2012,69:77-92.
[6]Bartle KD.Theory and principles of supercritical fluid chromatography//Smith RM.Supercritical fluid chromatography.Loughborough,UK:The Royal Society of Chemistry,1988:1-28.
[7]Ghinet A,Zehani Y,Lipka E.Supercritical fluid chromatography approach for a sustainable manufacture of new stereoisomeric anticancer agent.J Pharm Biomed Anal,2017,145:845-853.
[8]Desfontaine V,Guillarme D,Francotte E,et al.Supercritical fluid chromatography in pharmaceutical analysis.J Pharm Biomed Anal,2015,113:56-71.
[9]Wang RQ,Ong TT,Ng SC,et al.Recent advances in pharmaceutical separations with supercritical fluid chromatography using chiral stationary phases.Trends Anal Chem,2012,37:83-100.
[10]Zhao Y,Woo G,Thomas S,et al.Rapid method development for chiral separation in drug discovery using sample pooling and supercritical fluid chromatography-mass spectrometry.J Chromatogr A,2003,1003(1-2):157-166.
[11]Zou W,Dorsey JG,Chester TL.Modifier effects on column efficiency in packed-column supercritical luid chromatography.Anal Chem,2000,72(15):3620-3626.
[12]Kalíková K,Slechtová T,Vozka J,et al.Supercritical fluid chromatography as a tool for enantioselective separation;a review.Anal Chim Acta,2014,821:1-33.
[13]Salvador A,Herbreteau B,Dreux M,et al.Chiral supercritical fluid chromatography on porous graphitic carbon using commercial dimethyl beta-cyclodextrins as mobile phase additive.J Chromatogr A,2001,929(1-2):101-112.
[14]Speybrouck D,Doublet C,Cardinael P,et al.The effect of high concentration additive on chiral separations in supercritical fluid chromatography.J Chromatogr A,2017,1510:89-99.
[15]Vander Heyden Y,Mangelings D,Matthijs N,et al.Chiral separations//Ahuja S,Dong M.Handbook of pharmaceutical analysis by HPLC.Oxfrod,UK:Academic Press,2005:447-498.
[16]Chen H,Lv XY,Huang JM,et al.Investigation of retention and chiral recognition mechanism of the derivativeβ-cyclodextrin bonded stationary phase.Chem J Chin Univ,2000,21(4):562-565.(in Chinese)陈慧,吕宪禹,黄君珉,等.衍生化环糊精键合固定相色谱保留和手性识别机理的研究(I).高等学校化学学报,2000,21(4):562-565.
[17]Li X,Li YX,Zhang Y.Recent advances in enantio separating chiral drugs by CSP of HPLC.Appl Chem Ind,2014,43(6):1125-1127,1132.(in Chinese)李雪,李优鑫,张勇.高效液相色谱法手性固定相拆分手性药物研究进展.应用化工,2014,43(6):1125-1127,1132.
[18]Berthod A.Chiral recognition in separation methods--mechanisms and applications.Lyon,France:Springer,2010:1-31.
[19]Ikai T,Okamoto Y.Structure control of polysaccharide derivatives for efficient separation of enantiomers by chromatography.Chem Rev,2009,109(11):6077-6101.
[20]Lou X,Janssen HG,Cramers CA.Temperature and pressure effects on solubility in supercritical carbon dioxide and retention in supercritical fluid chromatography.J Chromatogr A,1997,785(1-2):57-64.
[21]?sberg D,Enmark M,Samuelsson J,et al.Evaluation of co-solvent fraction,pressure and temperature effects in analytical and preparative supercritical fluid chromatography.J Chromatogr A,2014,1374:254-260.
[22]Segawa H,Iwata YT,Yamamuro T,et al.Enantioseparation of methamphetamine by supercritical fluid chromatography with cellulose-based packed column.Forensic Sci Int,2017,273:39-44.
[23]Li L.Direct enantiomer determination of methorphan by HPLC-MSand SFC-MS.Forensic Chemi,2016,2:82-85.
[24]Berger TA,Berger BK.Chromatographic resolution of 7 of 8stereoisomers of vitamin K1 on an amylose stationary phase using supercritical fluid chromatography.Chromatographia,2013,76:549-552.
[25]Yang JF,Xu CL,Zhang J,et al.Determination of the enantiomer of iopmamidol by supercritical fluid chromatography.Chin J Mod Appl Pharm,2016,33(12):1566-1569.(in Chinese)杨杰峰,徐川龙,张洁,等.超临界流体色谱法测定碘帕醇的对映异构体.中国现代应用药学,2016,33(12):1566-1569.
[26]Jin W,Yang XL,Lu D,et al.Chiral separation of levetiracetam and R-enantiomer by supercritical fluid chromatography.Chin J Pharm Anal,2013,33(5):822-826.(in Chinese)金薇,杨新磊,陆丹,等.超临界流体色谱法手性拆分左乙拉西坦及其右旋异构体.药物分析杂志,2013,33(5):822-826.
[27]Chen XL,Li L.Chiral separation and determination of ropivacaine hydrochloride and dextroisomer in ropivacaine hydrochloride injection by SFC.Tianjin Pharm,2017,29(3):4-7.(in Chinese)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.天津药学,2017,29(3):4-7.
[28]Dai HX,Yang X,Lin CM.Enantioseparation of 1,4-dihydropyridines calcium antagonistsby supercritical fluid chromatography.Chin J Pharm Anal,2017,37(8):1513-1519.(in Chinese)戴慧雪,杨雪,林春绵.1,4-二氢吡啶类钙拮抗剂在超临界色谱中的对映体分离.药物分析杂志,2017,37(8):1513-1519.
[29]Chen WZ,Xu PX,Yi RZ,et al.Separation of phenylalanine methylester 5’-phosphoamidates of d4t diastereoisomers by supercritical fluid chromatography.Chin J Anal Chem,2012,40(8):1159-1163.(in Chinese)陈伟珠,许鹏翔,易瑞灶,等.超临界流体色谱法分析非对映异构体d4T-5’-N-磷酰化苯丙氨酸甲酯.分析化学研究报告,2012,40(8):1159-1163.
[30]Jin W,Lin H,Chen Y,et al.Chiral separation of ezetimibe and R-enantiomer by supercritical fluid chromatography.Chin Pharm J,2015,50(1):68-71.(in Chinese)金薇,林华,陈阳,等.依折麦布及其R-对映体的超临界流体色谱手性拆分方法研究.中国药学杂志,2015,50(1):68-71.
[31]Dai T,Huang JJ,Ji H,et al.Enantiomers separation of zileuton by supercritical fluid chromatography.West China J Pharm Sci,2012,27(1):67-69.(in Chinese)戴涛,黄珺珺,季红,等.超临界流体色谱拆分齐留通对映体.华西药学杂志,2012,27(1):67-69.
[32]Luo YH.Chiral separation of naproxen enantiomers by supercritical fluid chromatography.China Pharm,2015,26(24):4789-4791.(in Chinese)罗英豪.超临界流体色谱法拆分萘普生对映体.中国药房,2015,26(24):4789-4791.
[33]Toribio L,del Nozal MJ,Bernal JL,et al.Enantiomeric resolution of bifonazole by supercritical fluid chromatography.J Sep Sci,2015,29(10):1373-1378.
[34]Bao Z,Su B,Xing H,et al.Enantioseparation of racemic paroxol on an amylose-based chiral stationary phase by supercritical fluid chromatography.J Sep Sci,2015,33(20):3256-3262.
[35]Li DY,Wu X,Hao FL,et al.Separation of enantiomers by supercritical fluid chromatography on polysaccharide derivative-based chiral stationary phase.Chin J Chromatogr,2016,34(1):80-84.(in Chinese)李冬艳,吴锡,郝芳丽,等.多糖类手性固定相超临界流体色谱法分离手性化合物.色谱,2016,34(1):80-84.
[36]West C,Konjaria ML,Shashviashvili N,et al.Enantioseparation of novel chiral sulfoxides on chlorinated polysaccharide stationary phases in supercritical fluid chromatography.J Chromatogr A,2017,1499:174-182.
[37]Pokrovskiy OI,Ustinovich KB,Usovich OI,et al.A case of Z/E-isomers elution order inversion caused by cosolvent percentage change in supercritical fluid chromatography.J Chromatogr A,2017,1479:177-184.
[38]KalíkováK,MartínkováM,Schmid MG,et al.Cellulose tris-(3,5-dimethylphenylcarbamate)-based chiral stationary phase for the enantioseparation of drugs in supercritical fluid chromatography:comparison with HPLC.J Sep Sci,2018,41(6):1471-1478.
[39]Yu LJ,Huang HW,Li XM,et al.Determination of stereoisomers in landiolol hydrochloride by ultra performance convergence chromatography.Chin J Anal Chem,2016,44(9):1348-1353.(in Chinese)庾莉菊,黄海伟,李秀梅,等.超高效合相色谱法测定盐酸兰地洛尔中立体异构体的含量.分析化学,2016,44(9):1348-1353.
[40]Li SM,Lu YH,Gao L,et al.Study on the separation of cadotril enantiomers with ultra performance convergence chromatography.Chin J Anal Lab,2018,37(4):441-444.(in Chinese)李士敏,陆永辉,高莉,等.超高效合相色谱法拆分卡多曲对映体研究.分析试验室,2018,37(4):441-444.
[41]Wang B,Yan H,Wang SJ,et al.Separation of linalool enantiomer with ultra performance convergence chromatography and thermodynamic studies.J Instrumental Anal,2015,34(7):824-828.(in Chinese)王波,闫衡,王肃军,等.超高效合相色谱对芳樟醇对映体的拆分及热力学研究.分析测试学报,2015,34(7):824-828.