title: Comparative enantioseparation of talinolol in aqueous and non-aqueous capillary electrophoresis and study of related selector-selectand interactions by nuclear magnetic resonance spectroscopy.
abstract: The enantiomers of the chiral β-blocker drug talinolol were separated with two single component sulfated β-cyclodextrin (CD) derivatives, namely heptakis (2,3-di-O-methyl-6-sulfo)-β-CD) (HDMS-β-CD) and heptakis (2,3-di-O-acetyl-6-sulfo)-β-CD) (HDAS-β-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-β-CD was confirmed in aqueous buffer, while the complex between the enantiomers of talinolol and HDMS-β-CD was of the external type. The complex of the talinolol enantiomers with HDAS-β-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.
authors.affiliation: Institute of Physical and Analytical Chemistry, School of Exact and Natural Sciences, Tbilisi State University, Tbilisi, Georgia.
authors.forename: Lali
authors.initials: L
authors.lastname: Chankvetadze
authors.forename: Anne-Catherine
authors.initials: AC
authors.lastname: Servais
authors.forename: Marianne
authors.initials: M
authors.lastname: Fillet
authors.forename: Antonio
authors.initials: A
authors.lastname: Salgado
authors.forename: Jacques
authors.initials: J
authors.lastname: Crommen
authors.forename: Bezhan
authors.initials: B
authors.lastname: Chankvetadze
mesh_terms: D019075:Electrophoresis, Capillary / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D011412:Propanolamines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D011412:Propanolamines; C011550:talinolol