Mechanistic study on the opposite migration order of clenbuterol enantiomers in capillary electrophoresis with beta-cyclodextrin and single-isomer heptakis(2,3-diacetyl-6-sulfo)-beta-cyclodextrin |
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Authors: | Chankvetadze B Lomsadze K Bergenthal D Breitkreutz J Bergander K Blaschke G |
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Institution: | Institute of Pharmaceutical Chemistry, University of Münster, Germany. |
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Abstract: | Opposite migration order was observed for the enantiomers of the chiral beta2-adrenergic drug clenbuterol (CL) in capillary electrophoresis (CE) when resolved with native beta-cyclodextrin (beta-CD) and heptakis (2,3-diacetyl-6-sulfo)-beta-CD (HDAS-beta-CD). The possible mechanisms of the affinity reversal of the CL enantiomers depending on the structure of the CD were studied using 1H-nuclear magnetic resonance (1H-NMR) spectrometry and one-dimensional rotating frame nuclear Overhauser and exchange spectrometry (1-D ROESY). Significant differences were observed between the structure of the (+/-)-CL complexes with beta-CD and HDAS-beta-CD. |
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