Article (Scientific journals)
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.
Servais, Anne-Catherine; Rousseau, Anne; Dive, Georges et al.
2012In Journal of Chromatography. A, 1232, p. 59-64
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Abstract :
[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.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Servais, Anne-Catherine  ;  Université de Liège - ULiège > Département de pharmacie > Analyse des médicaments
Rousseau, Anne
Dive, Georges ;  Université de Liège - ULiège > Centre d'ingénierie des protéines
Frederich, Michel  ;  Université de Liège - ULiège > Département de pharmacie > Pharmacognosie
Crommen, Jacques ;  Université de Liège - ULiège > Département de pharmacie > Département de pharmacie
Fillet, Marianne ;  Université de Liège - ULiège > Département de pharmacie > Analyse des médicaments
Language :
English
Title :
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.
Publication date :
2012
Journal title :
Journal of Chromatography. A
ISSN :
0021-9673
eISSN :
1873-3778
Publisher :
Elsevier Science, Amsterdam, Netherlands
Volume :
1232
Pages :
59-64
Peer reviewed :
Peer Reviewed verified by ORBi
Commentary :
Copyright A(c) 2011 Elsevier B.V. All rights reserved.
Available on ORBi :
since 12 December 2011

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