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Capillary electrophoretic and nuclear magnetic resonance studies on the opposite affinity pattern of propranolol enantiomers towards various cyclodextrins |
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| Authors: | Anne‐Catherine Servais Anne Rousseau Marianne Fillet Ketevan Lomsadze Antonio Salgado Jacques Crommen Bezhan Chankvetadze |
| Affiliation: | 1. Department of Analytical Pharmaceutical Chemistry, Institute of Pharmacy, University of Liège, Liège, Belgium;2. Department of Physical and Analytical Chemistry, School of Exact and Natural Sciences, Tbilisi State University, Tbilisi, Georgia;3. Department of Medicinal Chemistry, Centro Nacional de Investigaciones Oncológicas (CNIO), Madrid, Spain |
| Abstract: | In the present study the migration order of the propranolol enantiomers with various native CDs and neutral and charged CD derivatives was examined in capillary electrophoresis (CE). The reversal of the enantiomer migration order was observed due to sulfation of β‐CD on its primary hydroxy groups. The structures of intermolecular selector‐select and temporary diastereomeric associates in solution were elucidated based on 1D rotating frame nuclear Overhauser effect spectroscopy (1D ROESY) experiments. Major structural differences were observed between the propranolol complexes with native β‐CD and heptakis(6‐O‐sulfo)‐β‐CD. |
| Keywords: | Capillary electrophoresis Cyclodextrins Enantiomer migration order NMR spectroscopy Propranolol Separation mechanisms |