A comprehensive study of the enantioseparation of chiral drugs by cyclodextrin using capillary electrophoresis combined with theoretical approaches.

作者: Libo Li , Xia Li , Quan Luo , Tianyan You

DOI: 10.1016/J.TALANTA.2015.04.039

关键词:

摘要: Four chiral drugs were enantioseparated by native beta-cyclodextrin (β-CD) and negatively charged carboxymethyl-beta-cyclodextrin (CM-β-CD) using capillary electrophoresis coupled with electrochemiluminescence detection (CE-ECL). Using 50 mM pH 5.5 Tris-H3PO4 10 CM-β-CD as a running buffer, high resolution efficiency could be obtained. With the help of isothermal titration calorimetry (ITC), nuclear magnetic resonance (NMR) molecular modeling, recognition mechanism was comprehensively investigated. Thermodynamic parameters data from ITC revealed that exhibited stronger binding affinity analytes than β-CD, driving forces responsible for mainly electrostatic interactions between positively analytes. In addition, both macroscopic microscopic point view, results NMR modeling investigation adequately confirm conclusion comparing stereochemical structures complexes. Combination ITC, techniques not only can assist CE to investigate discrimination mechanism, but also predict guide enantioseparation conversely.

参考文章(35)
Despina A. Tsioupi, Raluca-Ioana Stefan-vanStaden, Constantina P. Kapnissi-Christodoulou, Chiral selectors in CE: recent developments and applications. Electrophoresis. ,vol. 34, pp. 178- 204 ,(2013) , 10.1002/ELPS.201200239
Tamás Sohajda, Wen Hui Hu, Li Li Zeng, Hong Li, Lajos Szente, Béla Noszál, Szabolcs Béni, Evaluation of the interaction between sitagliptin and cyclodextrin derivatives by capillary electrophoresis and nuclear magnetic resonance spectroscopy ELECTROPHORESIS. ,vol. 32, pp. 2648- 2654 ,(2011) , 10.1002/ELPS.201000639
Min-Jie Xie, Yu-Qi Feng, Shi-Lu Da, Di-Ya Meng, Li-Wei Ren, Capillary electrophoresis and open tubular capillary electrochromatography using a magnesia–zirconia coated capillary Analytica Chimica Acta. ,vol. 428, pp. 255- 263 ,(2001) , 10.1016/S0003-2670(00)01228-9
FakhrEldin O. Suliman, Abdalla A. Elbashir, Enantiodifferentiation of chiral baclofen by β-cyclodextrin using capillary electrophoresis: A molecular modeling approach Journal of Molecular Structure. ,vol. 1019, pp. 43- 49 ,(2012) , 10.1016/J.MOLSTRUC.2012.03.055
Yanli YANG, Chenfu ZHU, Jian SHEN, Aiyou HAO, Enantioseparation in capillary electrophoresis using 6-oligo-(lactic acid)cyclomaltoheptaose as a chiral selector. Analytical Sciences. ,vol. 25, pp. 1315- 1318 ,(2009) , 10.2116/ANALSCI.25.1315
Mikhail Rekharsky, Yoshihisa Inoue, Chiral Recognition Thermodynamics of β-Cyclodextrin: The Thermodynamic Origin of Enantioselectivity and the Enthalpy−Entropy Compensation Effect Journal of the American Chemical Society. ,vol. 122, pp. 4418- 4435 ,(2000) , 10.1021/JA9921118
Shuye Wang, Yun Dai, Jianhua Wu, Jie Zhou, Jian Tang, Weihua Tang, Methoxyethylammonium monosubstituted β-cyclodextrin as the chiral selector for enantioseparation in capillary electrophoresis. Journal of Chromatography A. ,vol. 1277, pp. 84- 92 ,(2013) , 10.1016/J.CHROMA.2012.12.045
Anne-Catherine Servais, Anne Rousseau, Marianne Fillet, Ketevan Lomsadze, Antonio Salgado, Jacques Crommen, Bezhan Chankvetadze, Separation of propranolol enantiomers by CE using sulfated beta-CD derivatives in aqueous and non-aqueous electrolytes: Comparative CE and NMR study. Electrophoresis. ,vol. 31, pp. 1467- 1474 ,(2010) , 10.1002/ELPS.200900738