Comparative enantioseparation of talinolol in aqueous and non-aqueous capillary electrophoresis and study of related selector-selectand interactions by nuclear magnetic resonance spectroscopy.
Aqueous and non-aqueous capillary electrophoresis; Nuclear magnetic resonance spectroscopy; Enantioseparations; Cyclodextrins; Reversal of enantiomer migration order
Abstract :
[en] The enantiomers of the chiral beta-blocker drug talinolol were separated with two single component sulfated beta-cyclodextrin (CD) derivatives, namely heptakis (2,3-di-O-methyl-6-sulfo)-beta-CD) (HDMS-beta-CD) and heptakis (2,3-di-O-acetyl-6-sulfo)-beta-CD) (HDAS-beta-CD), in aqueous and non-aqueous capillary electrophoresis (CE). The enantiomer affinity pattern of talinolol toward these two CDs was opposite in both aqueous and non-aqueous CE. However, the enantiomer affinity pattern for a given CD derivative did not change when aqueous buffer was replaced with non-aqueous background electrolyte. The structures of the analyte-selector complexes in both, aqueous and non-aqueous electrolytes were studied using rotating frame nuclear Overhauser effect (ROESY) NMR spectroscopy. Inclusion complex formation between the enantiomers of talinolol and HDAS-beta-CD was confirmed in aqueous buffer, while the complex between the enantiomers of talinolol and HDMS-beta-CD was of the external type. The complex of the talinolol enantiomers with HDAS-beta-CD in non-aqueous electrolyte was also of the external type. In spite of external complex formation excellent separation of the enantiomers was observed in non-aqueous CE.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Chankvetadze, Lali
Servais, Anne-Catherine ; Université de Liège - ULiège > Département de pharmacie > Analyse des médicaments
Fillet, Marianne ; Université de Liège - ULiège > Département de pharmacie > Analyse des médicaments
Salgado, Antonio
Crommen, Jacques ; Université de Liège - ULiège > Département de pharmacie > Département de pharmacie
Chankvetadze, Bezhan
Language :
English
Title :
Comparative enantioseparation of talinolol in aqueous and non-aqueous capillary electrophoresis and study of related selector-selectand interactions by nuclear magnetic resonance spectroscopy.
Publication date :
2012
Journal title :
Journal of Chromatography. A
ISSN :
0021-9673
eISSN :
1873-3778
Publisher :
Elsevier, Amsterdam, Netherlands
Volume :
1267
Pages :
206-16
Peer reviewed :
Peer Reviewed verified by ORBi
Commentary :
Copyright (c) 2012 Elsevier B.V. All rights reserved.
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