开管毛细管电色谱在手性药物拆分方面的研究进展
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摘要
手性药物的有效拆分以及优化拆分条件对医药行业有着重大意义。本文就开管毛细管电色谱技术及其对手性药物的拆分研究进行展开简要概述综述,分别对糖类衍生物、金属-有机骨架化合物、大环抗生素、蛋白质等物质作为开管毛细管电色谱柱手性选择剂的制备和应用,以及各自的优缺点进行了简要综述,并对其做出展望,为开管毛细管电色谱技术对手性药物的拆分研究提供理论参考。
The chiral separations and identification of chiral drugs are gaining importance in pharmaceuticals and other fields. The research progress on chiral separations of drugs by using open tubular capillary electrochromatography( OTCE) was discussed. Chiral selective materials used in OTCE,such as derivatives of carbohydrate,metal organic frameworks,macrocyclic antibiotics and protein,were reviewed,their applications,advantages and disadvantages were also discussed. The trends and future challenges of the method were summarized,which would provide theory references for chiral drug separations in OTCE.
The chiral separations and identification of chiral drugs are gaining importance in pharmaceuticals and other fields. The research progress on chiral separations of drugs by using open tubular capillary electrochromatography( OTCE) was discussed. Chiral selective materials used in OTCE,such as derivatives of carbohydrate,metal organic frameworks,macrocyclic antibiotics and protein,were reviewed,their applications,advantages and disadvantages were also discussed. The trends and future challenges of the method were summarized,which would provide theory references for chiral drug separations in OTCE.
引文
[1]焦佳琪,薛燕斌,杨慧珍,等.分子印迹技术在药物提取领域的应用和展望[J].中国药物与临床,2018,18(2):214-218.
[2]卢小泉,张强,贾正平,等.金属卟啉类化合物开管毛细管柱的制备与评价[J].分析化学,2005(7):935-938.
[3]张欢欢,陈继,周孙英.纳米壳聚糖修饰的开管毛细管电色谱柱的制备及对碱性蛋白质的分离[J].高等学校化学学报,2015,36(4):631-637.
[4] Koppenhoefer B,Epperlein U, Christian B, et al. Separation of enatiomers of drugs by capillary electrophoresis III.β-cyclodextrinaschiral solvating agent[J]. Journal of Chromatography A,1996,735(1):333-343.
[5]邢文国,孟宪兴,冯维春,等. N-(2-羟丙基)三甲胺盐-β-环糊精的合成及其在非水毛细管电泳拆分酸性手性药物中的应用[J].分析试验室,2012,31(11):37-40.
[6]初永宝,蒋文强,崔凤霞,等.非水毛细管电泳对9种手性药物的拆分[J].色谱,2003(2):138-142.
[7]周大铮,娄子洋,武向峰,等.羟丙基-β-环糊精-毛细管电泳法分离伪麻黄碱[J].药学实践杂志,2001(1):24-25.
[8]徐婷婷.毛细管电色谱柱的研究进展[J].化工时刊,2017,31(6):15-17.
[9] Pretorius V,Hopkins B J,Schieke J D. Electroosmosis:A new concept for high-speed liquild chromatography[J]. Journal of Chromatography,1974,99:23-30.
[10] Tsuda T,Nomura K,Nakagawa G T. Open-tubular microcapillary liquid Chromatography with electroosmosis flow using a UV detector[J].Journal of Chromtography,1982,248(2):241-247.
[11]寇登民,云希勤.毛细管色谱柱涂渍方法的研究[J].精细石油化工,1992(4):60-63.
[12]颜霞,方智利,林纯,等.环糊精衍生物涂渍毛细管柱的制备及分离性能[J].应用化学,2013,30(8):957-962.
[13]谢敏杰,冯钰!,达世禄,等.β-环糊精键合蚀刻开管毛细管电色谱柱的制备与评价[J].分析测试学报,2003(5):33-36.
[14]王园朝.β-环糊精的溶胶一凝胶法电色谱开管柱的制备及评价[J].咸宁师专学报,2000(3):71-74.
[15]李方,靳慧,顾峻岭,等.用溶胶凝胶技术制备C8开管柱进行电色谱分离[J]. Journal of Beijing Institute of Technology(English Edition),1996(2):122.
[16]郁韵秋,陈燕,李妮,等.盐酸美普他酚的毛细管电泳手性分离[J].中国药学(英文版),2004(3):187-189.
[17]李英杰,吴婧,吕仁江,等.羧甲基-β-环糊精/SiO2/Ti O2毛细管开管柱的制备及其应用于毛细管电色谱[J].理化检验(化学分册),2014,50(2):161-165.
[18]聂桂珍.环糊精在手性电色谱中的应用研究[D].南昌:南昌大学,2014.
[19]韩苗苗.键合型纤维素基手性固定相的制备及其对商品药阿替洛尔的分离//中国化学会高分子学科委员会.中国化学会2017全国高分子学术论文报告会摘要集——主题A:高分子化学(1)[C].中国化学会高分子学科委员会:中国化学会,2017:2.
[20]杨清清,伍蓉,赵敬丹,等.开管型3,5-二氯苯基氨基甲酸酯纤维素衍生物键合手性毛细管电色谱柱的制备及应用[J].药物分析杂志,2011,31(11):2108-2113.
[21]董树清,高瑞斌,张霞,等.纳米纤维素在毛细管电泳手性分离中的应用//第八届全国微全分析系统学术会议、第三届全国微纳尺度生物分离分析学术会议暨第五届国际微化学与微系统学术会议论文集[C].中国科学院兰州化学物理研究所,甘肃中医学院,2013:1-1.
[22]董晓莉.新型手性固定相的制备及其在毛细管电色谱中的应用[D].杭州:浙江大学,2009.
[23]飞志欣.基于金属—有机骨架材料的毛细管电色谱手性分离研究[D].昆明:云南师范大学,2014.
[24]陶勇.金属—有机骨架材料用于毛细管电色谱手性分离的研究[D].昆明:云南师范大学,2015.
[25] Pan C J,Wang W F,Chen X G. In situ rapid preparation of homochiral metal-organic frameworkcoatedcolumn for open tubular capillary electrochromatography[J]. Journal of Chromatography A,2016,1427:125-133.
[26] Chen B,Du Y X,Wang H. Study on enantiomeric separation of basic drugs by NACE in methanol-basedmedium using erythromycin lactobionate as a chiral selector[J]. Electrophoresis,2010,31(2):371-377.
[27] Du Y,Chen B. Evaluation of the enantioseparation capability of the novel chiral selector clindamycin phosphate towards basic drugs by micellar electrokinetic chromatography[J]. J. Chromatogr. A,2010,1217:1806-1812.
[28] Jiang Z,Wang Z,Sussmuth R,et al. Highlighting the possible secondary interactions in the role of balhimycin and its analogues for enantiorecognition in capillary electrophoresis[J]. J. Chromatogr. A,2010,1217:1149-1156.
[29] Kumar A P,Park J H. Azithromycin as a new chiral selector in capillary electrophoresis[J]. Chromatogr. A,2011,1218:1314-1317.
[30] Ha P, Hoogmartens J, Schepdael A V. Recent advances in pharmaceutical applications of chiral capillary electrophoresis[J]. J.Pharm. Biomed. Anal.,2006,41:1-11.
[31] 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].Electrophoresis,2004,25:2625-2656.
[32]勾新磊,苏萍,张春婷,等.微波辅助合成法快速制备替考拉宁开管毛细管电色谱柱[J].分析试验室,2010(10):13-15.
[33]高也,邱百灵,梁启慧,等.卵白素-脂质体复合物作为开管毛细管电色谱的手性选择剂分离盐酸美西律(英文)[J]. Journal of Chinese Pharmaceutical Sciences,2017,26(12):872-880.
[34] Kitagawa F,Inoue K,Hasegawa T,et al. Chiral separation of acidic drug components by open tubular electrochromatography using avidin immobilized capillaries[J]. Journal of Chromatography A,2006,1130(2):219-226.
[35] Fu Q F,Zhang K L,Gao D,et al. Escherichia coli adhesive coating as a chiral stationary phase for open tubular capillary electrochromatography enantioseparation[J]. Analytica Chimica Acta,2017,969:63-71.
[36]郭贺影.聚多巴胺类涂层毛细管的制备及其在毛细管电色谱手性分离中的应用[D].兰州:兰州大学,2017.
[2]卢小泉,张强,贾正平,等.金属卟啉类化合物开管毛细管柱的制备与评价[J].分析化学,2005(7):935-938.
[3]张欢欢,陈继,周孙英.纳米壳聚糖修饰的开管毛细管电色谱柱的制备及对碱性蛋白质的分离[J].高等学校化学学报,2015,36(4):631-637.
[4] Koppenhoefer B,Epperlein U, Christian B, et al. Separation of enatiomers of drugs by capillary electrophoresis III.β-cyclodextrinaschiral solvating agent[J]. Journal of Chromatography A,1996,735(1):333-343.
[5]邢文国,孟宪兴,冯维春,等. N-(2-羟丙基)三甲胺盐-β-环糊精的合成及其在非水毛细管电泳拆分酸性手性药物中的应用[J].分析试验室,2012,31(11):37-40.
[6]初永宝,蒋文强,崔凤霞,等.非水毛细管电泳对9种手性药物的拆分[J].色谱,2003(2):138-142.
[7]周大铮,娄子洋,武向峰,等.羟丙基-β-环糊精-毛细管电泳法分离伪麻黄碱[J].药学实践杂志,2001(1):24-25.
[8]徐婷婷.毛细管电色谱柱的研究进展[J].化工时刊,2017,31(6):15-17.
[9] Pretorius V,Hopkins B J,Schieke J D. Electroosmosis:A new concept for high-speed liquild chromatography[J]. Journal of Chromatography,1974,99:23-30.
[10] Tsuda T,Nomura K,Nakagawa G T. Open-tubular microcapillary liquid Chromatography with electroosmosis flow using a UV detector[J].Journal of Chromtography,1982,248(2):241-247.
[11]寇登民,云希勤.毛细管色谱柱涂渍方法的研究[J].精细石油化工,1992(4):60-63.
[12]颜霞,方智利,林纯,等.环糊精衍生物涂渍毛细管柱的制备及分离性能[J].应用化学,2013,30(8):957-962.
[13]谢敏杰,冯钰!,达世禄,等.β-环糊精键合蚀刻开管毛细管电色谱柱的制备与评价[J].分析测试学报,2003(5):33-36.
[14]王园朝.β-环糊精的溶胶一凝胶法电色谱开管柱的制备及评价[J].咸宁师专学报,2000(3):71-74.
[15]李方,靳慧,顾峻岭,等.用溶胶凝胶技术制备C8开管柱进行电色谱分离[J]. Journal of Beijing Institute of Technology(English Edition),1996(2):122.
[16]郁韵秋,陈燕,李妮,等.盐酸美普他酚的毛细管电泳手性分离[J].中国药学(英文版),2004(3):187-189.
[17]李英杰,吴婧,吕仁江,等.羧甲基-β-环糊精/SiO2/Ti O2毛细管开管柱的制备及其应用于毛细管电色谱[J].理化检验(化学分册),2014,50(2):161-165.
[18]聂桂珍.环糊精在手性电色谱中的应用研究[D].南昌:南昌大学,2014.
[19]韩苗苗.键合型纤维素基手性固定相的制备及其对商品药阿替洛尔的分离//中国化学会高分子学科委员会.中国化学会2017全国高分子学术论文报告会摘要集——主题A:高分子化学(1)[C].中国化学会高分子学科委员会:中国化学会,2017:2.
[20]杨清清,伍蓉,赵敬丹,等.开管型3,5-二氯苯基氨基甲酸酯纤维素衍生物键合手性毛细管电色谱柱的制备及应用[J].药物分析杂志,2011,31(11):2108-2113.
[21]董树清,高瑞斌,张霞,等.纳米纤维素在毛细管电泳手性分离中的应用//第八届全国微全分析系统学术会议、第三届全国微纳尺度生物分离分析学术会议暨第五届国际微化学与微系统学术会议论文集[C].中国科学院兰州化学物理研究所,甘肃中医学院,2013:1-1.
[22]董晓莉.新型手性固定相的制备及其在毛细管电色谱中的应用[D].杭州:浙江大学,2009.
[23]飞志欣.基于金属—有机骨架材料的毛细管电色谱手性分离研究[D].昆明:云南师范大学,2014.
[24]陶勇.金属—有机骨架材料用于毛细管电色谱手性分离的研究[D].昆明:云南师范大学,2015.
[25] Pan C J,Wang W F,Chen X G. In situ rapid preparation of homochiral metal-organic frameworkcoatedcolumn for open tubular capillary electrochromatography[J]. Journal of Chromatography A,2016,1427:125-133.
[26] Chen B,Du Y X,Wang H. Study on enantiomeric separation of basic drugs by NACE in methanol-basedmedium using erythromycin lactobionate as a chiral selector[J]. Electrophoresis,2010,31(2):371-377.
[27] Du Y,Chen B. Evaluation of the enantioseparation capability of the novel chiral selector clindamycin phosphate towards basic drugs by micellar electrokinetic chromatography[J]. J. Chromatogr. A,2010,1217:1806-1812.
[28] Jiang Z,Wang Z,Sussmuth R,et al. Highlighting the possible secondary interactions in the role of balhimycin and its analogues for enantiorecognition in capillary electrophoresis[J]. J. Chromatogr. A,2010,1217:1149-1156.
[29] Kumar A P,Park J H. Azithromycin as a new chiral selector in capillary electrophoresis[J]. Chromatogr. A,2011,1218:1314-1317.
[30] Ha P, Hoogmartens J, Schepdael A V. Recent advances in pharmaceutical applications of chiral capillary electrophoresis[J]. J.Pharm. Biomed. Anal.,2006,41:1-11.
[31] 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].Electrophoresis,2004,25:2625-2656.
[32]勾新磊,苏萍,张春婷,等.微波辅助合成法快速制备替考拉宁开管毛细管电色谱柱[J].分析试验室,2010(10):13-15.
[33]高也,邱百灵,梁启慧,等.卵白素-脂质体复合物作为开管毛细管电色谱的手性选择剂分离盐酸美西律(英文)[J]. Journal of Chinese Pharmaceutical Sciences,2017,26(12):872-880.
[34] Kitagawa F,Inoue K,Hasegawa T,et al. Chiral separation of acidic drug components by open tubular electrochromatography using avidin immobilized capillaries[J]. Journal of Chromatography A,2006,1130(2):219-226.
[35] Fu Q F,Zhang K L,Gao D,et al. Escherichia coli adhesive coating as a chiral stationary phase for open tubular capillary electrochromatography enantioseparation[J]. Analytica Chimica Acta,2017,969:63-71.
[36]郭贺影.聚多巴胺类涂层毛细管的制备及其在毛细管电色谱手性分离中的应用[D].兰州:兰州大学,2017.