Reference : Combination of capillary electrophoresis, molecular modelling and nuclear magnetic re...
Scientific journals : Article
Human health sciences : Pharmacy, pharmacology & toxicology
http://hdl.handle.net/2268/105158
Combination of capillary electrophoresis, molecular modelling and nuclear magnetic resonance to study the interaction mechanisms between single-isomer anionic cyclodextrin derivatives and basic drug enantiomers in a methanolic background electrolyte.
English
Servais, Anne-Catherine mailto [Université de Liège - ULg > Département de pharmacie > Analyse des médicaments]
Rousseau, Anne []
Dive, Georges mailto [Université de Liège - ULg > > Centre d'ingénierie des protéines]
Frederich, Michel mailto [Université de Liège - ULg > Département de pharmacie > Pharmacognosie >]
Crommen, Jacques mailto [Université de Liège - ULg > Département de pharmacie > Département de pharmacie]
Fillet, Marianne mailto [Université de Liège - ULg > Département de pharmacie > Analyse des médicaments]
2012
Journal of Chromatography. A
Elsevier Science
1232
59-64
Yes (verified by ORBi)
International
0021-9673
1873-3778
Amsterdam
The Netherlands
[en] In order to improve our knowledge of the mechanisms of enantiomer recognition pattern in nonaqueous systems, an approach combining nonaqueous CE (NACE), molecular modelling and NMR was undertaken. Bupivacaine and propranolol were selected as model compounds and their interactions with two single-isomer highly charged beta-CD derivatives, namely heptakis(2,3-di-O-methyl-6-O-sulfo)-beta-CD (HDMS-beta-CD) and heptakis(2,3-di-O-acetyl-6-O-sulfo)-beta-CD (HDAS-beta-CD), were studied. The CD-bupivacaine complexes were evaluated by 2-D Rotating-frame Overhauser Effect SpectroscopY (ROESY) experiments. From these experiments, it can be assumed that inclusion complexes are not formed, whatever the CD derivative used. Molecular modelling was performed at the RHF/MINI-1 or B3LYP/6-31G(d) level. External as well as inclusion type complexes with the alkyl chain of propranolol into both CD cavities were located. Interaction energies calculated for bupivacaine and propranolol correlated with the enantiomer migration order observed in the NACE experiments using both anionic CD derivatives. The interaction of propranolol with HDMS-beta-CD or HDAS-beta-CD gives rise to a family of external and inclusion complexes in which some are more probably obtained.
http://hdl.handle.net/2268/105158
10.1016/j.chroma.2011.10.010
Copyright A(c) 2011 Elsevier B.V. All rights reserved.

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