Capillary electrophoretic and nuclear magnetic resonance studies on the opposite affinity pattern of propranolol enantiomers towards various cyclodextrins

Servais, Anne-Catherine; Rousseau, Anne; Fillet, Marianne; Lomsadze, Ketevan; Salgado, Antonio; Crommen, Jacques; Chankvetadze, Bezhan

doi:10.1002/jssc.201000040

Article (Scientific journals)

Capillary electrophoretic and nuclear magnetic resonance studies on the opposite affinity pattern of propranolol enantiomers towards various cyclodextrins

Servais, Anne-Catherine; Rousseau, Anne; Fillet, Marianne et al.

2010 • In Journal of Separation Science, 33, p. 1617-1624

Peer Reviewed verified by ORBi

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https://hdl.handle.net/2268/11324

DOI
10.1002/jssc.201000040

PubMed
20437416

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Keywords :

Capillary electrophoresis; NMR spectroscopy; Enantiomer migration order; Separation mechanisms; Cyclodextrins; Propranolol

Abstract :

[en] 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-selectand 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.

Disciplines :

Pharmacy, pharmacology & toxicology

Author, co-author :

Servais, Anne-Catherine ; Université de Liège - ULiège > Département de pharmacie > Analyse des médicaments

Rousseau, Anne ; Université de Liège - ULiège > Département de pharmacie > Analyse des médicaments

Fillet, Marianne ; Université de Liège - ULiège > Département de pharmacie > Analyse des médicaments

Lomsadze, Ketevan; Tbilisi State University

Salgado, Antonio; Centro Nacional de Investigaciones Oncológicas

Crommen, Jacques ; Université de Liège - ULiège > Département de pharmacie > Analyse des médicaments

Chankvetadze, Bezhan; Tbilisi State University

Language :

English

Title :

Capillary electrophoretic and nuclear magnetic resonance studies on the opposite affinity pattern of propranolol enantiomers towards various cyclodextrins

Publication date :

2010

Journal title :

Journal of Separation Science

ISSN :

1615-9306

eISSN :

1615-9314

Publisher :

Wiley-VCH Verlag Gmbh, Weinheim, Germany

Volume :

Pages :

1617-1624

Peer reviewed :

Peer Reviewed verified by ORBi

Funders :

GNSF - Georgian National Science Foundation
MSD - Merck Sharp and Dohme
F.R.S.-FNRS - Fonds de la Recherche Scientifique

Available on ORBi :

since 09 April 2010

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