二维液相色谱技术在药物分析中的应用
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摘要
二维液相色谱技术以其峰容量大、选择性高、分离能力强等突出优点,逐渐成为解决复杂样品分离难题的重要手段,尤其是在药品、食品、体内外代谢产物等领域的研究应用发展迅猛。笔者旨在论述二维液相色谱不同分离模式在药品质量控制中的应用研究及其发展前景。
Two dimensional liquid chromatography( 2 D-LC) has become an important way to achieve the separation of complex samples due to higher peak capacity,higher selectivity and better separation ability compared with one-dimensional liquid chromatography( 1 D-LC). 2 D-LC has been developing rapidly in many fields,such as medicine,food,metabolites in vivo or in vitro and so on.This review illustrates various separation modes of 2 D-LC and its applications and developments,with emphases on the research of quality control of drugs.
Two dimensional liquid chromatography( 2 D-LC) has become an important way to achieve the separation of complex samples due to higher peak capacity,higher selectivity and better separation ability compared with one-dimensional liquid chromatography( 1 D-LC). 2 D-LC has been developing rapidly in many fields,such as medicine,food,metabolites in vivo or in vitro and so on.This review illustrates various separation modes of 2 D-LC and its applications and developments,with emphases on the research of quality control of drugs.
引文
[1] ERNI F,FREI R W. Two-dimensional column liquid chromatographic technique for resolution of complex mixture[J]. J Chromatogr A,1978,149:561-569.
[2] WANG Z C,ZHANG Q H,ZHAO Z Y,et al. The switching technigue of two-dimensional liguid chromatography and its applications[J]. Chin J Anal Chem(分析化学),2005,33(5):722-728.
[3] DUGO P,CACCIOLA F,KUMM T,et al. Comprehensive multidimensional liquid chromatography:theory and applications[J].J Chromatogr A,2008,1184(1):353-368.
[4] GILAR M,DALY A E,KELE M,et al. Implications of column peak capacity on the separation of complex peptide mixtures in single-and two-dimensional high-performance liquid chromatography[J]. J Chromatogr A,2004,1061(2):183-192.
[5] LIU Z Y,PATTERSON D G,LEE M L. Geometric approach to factor analysis for the estimation of orthogonality and practical peak capacity in comprehensive two-dimensional separations[J].Anal Chem,1995,67(21):3840-3845.
[6]ˇCESLA P,HAJEK T,JANDERA P. Optimization of two-dimensional gradient liquid chromatography separations[J]. J Chromatogr A,2009,1216(16):3443-3457.
[7] LIU Z Y,PATTERSON D G,LEE M L. Geometric approach to factor analysis for the estimation of orthogonality and practical peak capacity in comprehensive two-dimensional separations[J].Anal Chem,1995,67(21):3840-3845.
[8] BAKAIN R A,RIVALS I,SASSIAT P,et al. Comparison of different statistical approaches to evaluate the orthogonality of chromatographic separations:application to reverse phase systems[J]. J Chromatogr A,2011,1218(20):2963-2975.
[9] GILAR M,FRIDRICH J,SCHURE M R,et al. Comparison of orthogonality estimation methods for the two-dimensional separations of peptides[J]. Anal Chem,2012,84(20):8722-8732.
[10] POURHAGHIGHI M R,KARZAND M,GIRAULT H H. Orthogonality of two-dimensional separations based on conditional entropy[J]. Anal Chem,2011,83(20):7676-7681.
[11] SLONECKERP J,LI X,RIDGWAYT H,et al. Informational orthogonality of two-dimensional chromatographic separations[J].Anal Chem,1996,68(4):682-689.
[12] GILAR M,OLIVOVA P,DALY A E,et al. Orthogonality of separation in two-dimensional liquid chromatography[J]. Anal Chem,2005,77(19):6426-6434.
[13] GYSEGHEM E V,JIMIDAR M,SNEYERS R,et al. Orthogonality and similarity within silica-based reversed-phased chromatographic systems[J]. J Chromatogr A,2005,1074(1-2):117-131.
[14] FORLAY-FRICK P,GYSEGHEM E V,HEBERGER K,et al. Selection of orthogonal chromatographic systems based on parametric and non-parametric statistical tests[J]. Anal Chim Acta,2005,539(1):1-10.
[15] FAN W Z,ZHANG Y,CARR P W,et al. Application of snyderdolan classification scheme to the selection of"orthogonal"columns for fast screening of illicit drugs and impurity profiling of pharmaceuticals--I. Isocratic elution[J]. J Chromatogr A,2009,1216(38):6587-6599.
[16] TIAN D,ZHU D L,XU Z Q,et al. Separation and characterization of phenolic compounds in Chuju by two-dimensional hydrophilic interaction/reversed phase liquid chromatography coupled to diode array detection[J]. J Instr Anal(分析测试学报),2015,34(8):917-922.
[17] MATEJICEK D. Multi heart-cutting two-dimensional liquid chromatography-atmospheric pressure photoionization-tandem mass spectrometry method for the determination of endocrine disrupting compounds in water[J]. J Chromatogr A,2012,1231:52-58.
[18] NEUE U D. Theory of peak capacity in gradient elution[J]. J Chromatogr A,2005,1079(1-2):153-161.
[19] LAN T,JIAO F L,TANG T. Establishment and application of a two-dimensional liquid chromatographic system(NPLC×RPLC)[J]. Chin J Chromatogr(色谱),2008,26(3):374-377.
[20] JANDERA P,HAJEK T,STANKOVA M,et al. Optimization of comprehensive two-dimensional gradient chromatography coupling in-line hydrophilic interaction and reversed phase liquid chromatography[J]. J Chromatogr A,2012,1268:91-101.
[21] JANDERA P,HAJEK T,CESLA P. Effects of the gradient profile,sample volume and solvent on the separation in very fast gradients,with special attention to the second-dimension gradient in comprehensive two-dimensional liquid chromatography[J]. J Chromatogr A,2011,1218(15):1995-2006.
[22] DUGO P,FAVOINO O,LUPPINO R,et al. Comprehensive twodimensional normal-phase(adsorption)-reversed-phase liquid chromatography[J]. Anal Chem,2004,76(9):2525-2530.
[23] ZHANG Y H,ZHANG D W,CAO Y,et al. Simultaneous determination of vitamins A,D in vitamin A and D pharmaceutical by online two-dimensional reverse-phase liquid chromatography[J]. J Instr Anal(分析测试学报),2016,35(1):28-34.
[24] MURPHY R E,SCHURE M R,FOLEY J P. Effect of sampling rate on resolution in comprehensive two-dimensional liquid chromatography[J]. Anal Chem,1998,70(8):1585-1594.
[25] LIU Y M,GUO Z M,JIN Y,et al."Click oligo(ethylene glycol)":an excellent orthogonal stationary phase to C18 for two-dimensional reversed-phase/reversed-phase liquid chromatography[J]. J Chromatogr A,2008,1206(2):153-159.
[26] FRANCOIS I,CABOOTER D,SANDRA K,et al. Tryptic digest analysis by comprehensive reversed phasextwo reversed phase liquid chromatography(RP-LC×2RP-LC)at different pH's[J]. J Sep Sci,2009,32(8):1137-1144.
[27] QIAO X,SONG W,JI S,et al. Separation and characterization of phenolic compounds andtriterpenoid saponins in licorice(Glycyrrhiza uralensis)using mobilephase-dependent reversed-phase×reversed-phase comprehensivetwo-dimensional liquid chromatography coupled with massspectrometry[J]. J Chromatogr A,2015,1402:36-45.
[28] QIAO X,WANG Q,SONG W,et al. A chemical profiling solution for Chinese medicine formulas using comprehensive and loopbased multiple heart-cutting two-dimensional liquid chromatography coupled with quadrupole time-of-flight mass spectrometry[J]. J Chromatogr A,2016,1438:198-204.
[29] GILAR M,OLIVOVA P,DALY A E,et al. Two-dimensional separation of peptides using RP-RP-HPLC system with different pH in first and second separation dimensions[J]. J Sep Sci,2015,28(14):1694-1703.
[30] YAO C L,YANG W Z,WU W Y,et al. Simultaneous quantitation of five Panax notoginseng,saponins by multi heart-cutting two-dimensional liquid chromatography:method development and application to the quality control of eight notoginseng containing Chinese patent medicines[J]. J Chromatogr A,2015,1402:71-81.
[31] MINSHULL T C,COLE J,DOCKRELL D H,et al. Analysis of histone post translational modifications in primary monocyte derived macrophages using reverse phase×reverse phase chromatography in conjunction with porous graphitic carbon stationary phase[J]. J Chromatogr A,2016,1453:43-53.
[32] MENA-BRAVO A,PRIEGO-CAPOTE F,CASTRO L D.Two-dimensional liquid chromatography coupled to tandem mass spectrometry for vitamin D metabolite profiling including the C3-epimer-25-monohydroxyvitamin D3[J]. J Chromatogr A,2016,1451:50-57.
[33] ZHANG Y,JIN H L,LI X L,et al. Separation and characterization of bufadienolides in toad skin using two-dimensional normalphase liquid chromatography A reversed-phase liquid chromatography coupled with mass spectrometry[J]. J Chromatogr B Analyt Technol Biomed Life Sci,2016,1026:67-74.
[34] WANG X Y,LI J F,JIAN Y M,et al. On-line comprehensive twodimensional normal-phase liquidchromatography×reversed-phase liquid chromatography forpreparative isolation of Peucedanumpraeruptorum[J]. J Chromatogr A,2015,1387:60-68.
[35] LI J F,FANG H,YAN X,et al. On-line comprehensive two-dimensional normal-phase liquid chromatography×reversed-phase liquid chromatography for preparative isolation of toad venom[J].J Chromatogr A,2016,1456:169-175.
[36] CACCIOLA F,DELMONTE P,JAWORSKA K,et al. Employing ultra high pressure liquid chromatography as the second dimension in a comprehensive two-dimensional system for analysis of Stevia rebaudiana extracts[J]. J Chromatogr A,2011,1218(15):2012-2018.
[37] YANG W Z,ZHANG J X,YAO C L,et al. Method development and application of offline two-dimensional liquid chromatography/quadrupole time-of-flight mass spectrometry-fast data directed analysis for comprehensive characterization of the saponins from Xueshuantong Injection[J]. J Pharm Biomed Anal,2016,128:322-332.
[38] SUN W Y,TONG L,MIAO J Z,et al. Separation and analysis of phenolic acids from Salvia miltiorrhiza and its related preparations by off-line two-dimensional hydrophilicinteraction chromatography×reversed-phase liquid chromatographycoupled with ion trap timeof-flight mass spectrometry[J]. J Chromatogr A,2016,1431:79-88.
[39] GOLIZEH M,GEIB T,SLENO L. Identification of 4-hydroxynonenal protein targets in rat,mouse and human liver microsomes by two-dimensional liquid chromatography/tandem mass spectrometry[J].Rapid Commun Mass Spectrom,2016,30(13):1488-1494.
[40] LI Y,GU C,GRUENHAGEN J,et al. A size exclusion-reversed phase two dimensional-liquid chromatography methodology for stability and small molecule related species in antibody drug conjugates[J]. J Chromatogr A,2015,1393:81-88.
[41] LI Y,STELLA C,ZHENG L,et al. Investigation of low recovery in the free drug assay for antibody drug conjugates by size exclusion—reversed phase two dimensional-liquid chromatography[J].J Chromatogr B,2016,1032:112-118.
[42] WANG Y,KONG L,HU L H,et al. Biological fingerprinting analysis of the traditional Chinese prescription Longdan Xiegan Decoction by on/off-linecomprehensive two-dimensional biochromatography[J]. J Chromatogr B,2007,860(2):185-194.
[43] CHEN X F,CAO Y,ZHANG H,et al. Comparative normal/failing rat myocardium cell membrane chromatographic analysis system for screening specific components that counteract doxorubicininduced heart failure from Acontium carmichaeli[J]. Anal Chem,2014,86(10):4748-4757.
[44] JIA D,CHEN X F,CAO Y,et al. On-line comprehensive twodimensional HepG2 cell membrane chromatographic analysis system for charactering anti-hepatoma components from rat serum after oral administration of Radix Scutellariae:a strategy for rapid screening active compounds in vivo[J]. J Pharm Biomed Anal,2016,118:27-33.
[45] YANG Y,ROSALES-CONRADO N,GUILLEN-CASLA V,et al. Chiral determination of salbutamol,salmeterol and atenolol by two-dimensional LC-LC:application to urine samples[J]. Chromatographia,2012,75(23-24):1365-1375.
[46] VVENKATRAMANI C J,WIGMAN L,MISTRY K,et al. Simultaneous,sequential quantitative achiral-chiral analysis by twodimensional liquid chromatography[J]. J Sep Sci,2015,35(14):1748-1754.
[47] SONG Y L,JING W H,DU G,et al. Qualitative analysis and enantiospecific determination of angular-type pyranocoumarins in Peucedani Radix using achiral and chiral liquid chromatography coupled with tandem mass spectrometry[J]. J Chromatogr A,2014,1338:24-37.
[2] WANG Z C,ZHANG Q H,ZHAO Z Y,et al. The switching technigue of two-dimensional liguid chromatography and its applications[J]. Chin J Anal Chem(分析化学),2005,33(5):722-728.
[3] DUGO P,CACCIOLA F,KUMM T,et al. Comprehensive multidimensional liquid chromatography:theory and applications[J].J Chromatogr A,2008,1184(1):353-368.
[4] GILAR M,DALY A E,KELE M,et al. Implications of column peak capacity on the separation of complex peptide mixtures in single-and two-dimensional high-performance liquid chromatography[J]. J Chromatogr A,2004,1061(2):183-192.
[5] LIU Z Y,PATTERSON D G,LEE M L. Geometric approach to factor analysis for the estimation of orthogonality and practical peak capacity in comprehensive two-dimensional separations[J].Anal Chem,1995,67(21):3840-3845.
[6]ˇCESLA P,HAJEK T,JANDERA P. Optimization of two-dimensional gradient liquid chromatography separations[J]. J Chromatogr A,2009,1216(16):3443-3457.
[7] LIU Z Y,PATTERSON D G,LEE M L. Geometric approach to factor analysis for the estimation of orthogonality and practical peak capacity in comprehensive two-dimensional separations[J].Anal Chem,1995,67(21):3840-3845.
[8] BAKAIN R A,RIVALS I,SASSIAT P,et al. Comparison of different statistical approaches to evaluate the orthogonality of chromatographic separations:application to reverse phase systems[J]. J Chromatogr A,2011,1218(20):2963-2975.
[9] GILAR M,FRIDRICH J,SCHURE M R,et al. Comparison of orthogonality estimation methods for the two-dimensional separations of peptides[J]. Anal Chem,2012,84(20):8722-8732.
[10] POURHAGHIGHI M R,KARZAND M,GIRAULT H H. Orthogonality of two-dimensional separations based on conditional entropy[J]. Anal Chem,2011,83(20):7676-7681.
[11] SLONECKERP J,LI X,RIDGWAYT H,et al. Informational orthogonality of two-dimensional chromatographic separations[J].Anal Chem,1996,68(4):682-689.
[12] GILAR M,OLIVOVA P,DALY A E,et al. Orthogonality of separation in two-dimensional liquid chromatography[J]. Anal Chem,2005,77(19):6426-6434.
[13] GYSEGHEM E V,JIMIDAR M,SNEYERS R,et al. Orthogonality and similarity within silica-based reversed-phased chromatographic systems[J]. J Chromatogr A,2005,1074(1-2):117-131.
[14] FORLAY-FRICK P,GYSEGHEM E V,HEBERGER K,et al. Selection of orthogonal chromatographic systems based on parametric and non-parametric statistical tests[J]. Anal Chim Acta,2005,539(1):1-10.
[15] FAN W Z,ZHANG Y,CARR P W,et al. Application of snyderdolan classification scheme to the selection of"orthogonal"columns for fast screening of illicit drugs and impurity profiling of pharmaceuticals--I. Isocratic elution[J]. J Chromatogr A,2009,1216(38):6587-6599.
[16] TIAN D,ZHU D L,XU Z Q,et al. Separation and characterization of phenolic compounds in Chuju by two-dimensional hydrophilic interaction/reversed phase liquid chromatography coupled to diode array detection[J]. J Instr Anal(分析测试学报),2015,34(8):917-922.
[17] MATEJICEK D. Multi heart-cutting two-dimensional liquid chromatography-atmospheric pressure photoionization-tandem mass spectrometry method for the determination of endocrine disrupting compounds in water[J]. J Chromatogr A,2012,1231:52-58.
[18] NEUE U D. Theory of peak capacity in gradient elution[J]. J Chromatogr A,2005,1079(1-2):153-161.
[19] LAN T,JIAO F L,TANG T. Establishment and application of a two-dimensional liquid chromatographic system(NPLC×RPLC)[J]. Chin J Chromatogr(色谱),2008,26(3):374-377.
[20] JANDERA P,HAJEK T,STANKOVA M,et al. Optimization of comprehensive two-dimensional gradient chromatography coupling in-line hydrophilic interaction and reversed phase liquid chromatography[J]. J Chromatogr A,2012,1268:91-101.
[21] JANDERA P,HAJEK T,CESLA P. Effects of the gradient profile,sample volume and solvent on the separation in very fast gradients,with special attention to the second-dimension gradient in comprehensive two-dimensional liquid chromatography[J]. J Chromatogr A,2011,1218(15):1995-2006.
[22] DUGO P,FAVOINO O,LUPPINO R,et al. Comprehensive twodimensional normal-phase(adsorption)-reversed-phase liquid chromatography[J]. Anal Chem,2004,76(9):2525-2530.
[23] ZHANG Y H,ZHANG D W,CAO Y,et al. Simultaneous determination of vitamins A,D in vitamin A and D pharmaceutical by online two-dimensional reverse-phase liquid chromatography[J]. J Instr Anal(分析测试学报),2016,35(1):28-34.
[24] MURPHY R E,SCHURE M R,FOLEY J P. Effect of sampling rate on resolution in comprehensive two-dimensional liquid chromatography[J]. Anal Chem,1998,70(8):1585-1594.
[25] LIU Y M,GUO Z M,JIN Y,et al."Click oligo(ethylene glycol)":an excellent orthogonal stationary phase to C18 for two-dimensional reversed-phase/reversed-phase liquid chromatography[J]. J Chromatogr A,2008,1206(2):153-159.
[26] FRANCOIS I,CABOOTER D,SANDRA K,et al. Tryptic digest analysis by comprehensive reversed phasextwo reversed phase liquid chromatography(RP-LC×2RP-LC)at different pH's[J]. J Sep Sci,2009,32(8):1137-1144.
[27] QIAO X,SONG W,JI S,et al. Separation and characterization of phenolic compounds andtriterpenoid saponins in licorice(Glycyrrhiza uralensis)using mobilephase-dependent reversed-phase×reversed-phase comprehensivetwo-dimensional liquid chromatography coupled with massspectrometry[J]. J Chromatogr A,2015,1402:36-45.
[28] QIAO X,WANG Q,SONG W,et al. A chemical profiling solution for Chinese medicine formulas using comprehensive and loopbased multiple heart-cutting two-dimensional liquid chromatography coupled with quadrupole time-of-flight mass spectrometry[J]. J Chromatogr A,2016,1438:198-204.
[29] GILAR M,OLIVOVA P,DALY A E,et al. Two-dimensional separation of peptides using RP-RP-HPLC system with different pH in first and second separation dimensions[J]. J Sep Sci,2015,28(14):1694-1703.
[30] YAO C L,YANG W Z,WU W Y,et al. Simultaneous quantitation of five Panax notoginseng,saponins by multi heart-cutting two-dimensional liquid chromatography:method development and application to the quality control of eight notoginseng containing Chinese patent medicines[J]. J Chromatogr A,2015,1402:71-81.
[31] MINSHULL T C,COLE J,DOCKRELL D H,et al. Analysis of histone post translational modifications in primary monocyte derived macrophages using reverse phase×reverse phase chromatography in conjunction with porous graphitic carbon stationary phase[J]. J Chromatogr A,2016,1453:43-53.
[32] MENA-BRAVO A,PRIEGO-CAPOTE F,CASTRO L D.Two-dimensional liquid chromatography coupled to tandem mass spectrometry for vitamin D metabolite profiling including the C3-epimer-25-monohydroxyvitamin D3[J]. J Chromatogr A,2016,1451:50-57.
[33] ZHANG Y,JIN H L,LI X L,et al. Separation and characterization of bufadienolides in toad skin using two-dimensional normalphase liquid chromatography A reversed-phase liquid chromatography coupled with mass spectrometry[J]. J Chromatogr B Analyt Technol Biomed Life Sci,2016,1026:67-74.
[34] WANG X Y,LI J F,JIAN Y M,et al. On-line comprehensive twodimensional normal-phase liquidchromatography×reversed-phase liquid chromatography forpreparative isolation of Peucedanumpraeruptorum[J]. J Chromatogr A,2015,1387:60-68.
[35] LI J F,FANG H,YAN X,et al. On-line comprehensive two-dimensional normal-phase liquid chromatography×reversed-phase liquid chromatography for preparative isolation of toad venom[J].J Chromatogr A,2016,1456:169-175.
[36] CACCIOLA F,DELMONTE P,JAWORSKA K,et al. Employing ultra high pressure liquid chromatography as the second dimension in a comprehensive two-dimensional system for analysis of Stevia rebaudiana extracts[J]. J Chromatogr A,2011,1218(15):2012-2018.
[37] YANG W Z,ZHANG J X,YAO C L,et al. Method development and application of offline two-dimensional liquid chromatography/quadrupole time-of-flight mass spectrometry-fast data directed analysis for comprehensive characterization of the saponins from Xueshuantong Injection[J]. J Pharm Biomed Anal,2016,128:322-332.
[38] SUN W Y,TONG L,MIAO J Z,et al. Separation and analysis of phenolic acids from Salvia miltiorrhiza and its related preparations by off-line two-dimensional hydrophilicinteraction chromatography×reversed-phase liquid chromatographycoupled with ion trap timeof-flight mass spectrometry[J]. J Chromatogr A,2016,1431:79-88.
[39] GOLIZEH M,GEIB T,SLENO L. Identification of 4-hydroxynonenal protein targets in rat,mouse and human liver microsomes by two-dimensional liquid chromatography/tandem mass spectrometry[J].Rapid Commun Mass Spectrom,2016,30(13):1488-1494.
[40] LI Y,GU C,GRUENHAGEN J,et al. A size exclusion-reversed phase two dimensional-liquid chromatography methodology for stability and small molecule related species in antibody drug conjugates[J]. J Chromatogr A,2015,1393:81-88.
[41] LI Y,STELLA C,ZHENG L,et al. Investigation of low recovery in the free drug assay for antibody drug conjugates by size exclusion—reversed phase two dimensional-liquid chromatography[J].J Chromatogr B,2016,1032:112-118.
[42] WANG Y,KONG L,HU L H,et al. Biological fingerprinting analysis of the traditional Chinese prescription Longdan Xiegan Decoction by on/off-linecomprehensive two-dimensional biochromatography[J]. J Chromatogr B,2007,860(2):185-194.
[43] CHEN X F,CAO Y,ZHANG H,et al. Comparative normal/failing rat myocardium cell membrane chromatographic analysis system for screening specific components that counteract doxorubicininduced heart failure from Acontium carmichaeli[J]. Anal Chem,2014,86(10):4748-4757.
[44] JIA D,CHEN X F,CAO Y,et al. On-line comprehensive twodimensional HepG2 cell membrane chromatographic analysis system for charactering anti-hepatoma components from rat serum after oral administration of Radix Scutellariae:a strategy for rapid screening active compounds in vivo[J]. J Pharm Biomed Anal,2016,118:27-33.
[45] YANG Y,ROSALES-CONRADO N,GUILLEN-CASLA V,et al. Chiral determination of salbutamol,salmeterol and atenolol by two-dimensional LC-LC:application to urine samples[J]. Chromatographia,2012,75(23-24):1365-1375.
[46] VVENKATRAMANI C J,WIGMAN L,MISTRY K,et al. Simultaneous,sequential quantitative achiral-chiral analysis by twodimensional liquid chromatography[J]. J Sep Sci,2015,35(14):1748-1754.
[47] SONG Y L,JING W H,DU G,et al. Qualitative analysis and enantiospecific determination of angular-type pyranocoumarins in Peucedani Radix using achiral and chiral liquid chromatography coupled with tandem mass spectrometry[J]. J Chromatogr A,2014,1338:24-37.