titoli, abstracts, parole chiave >>>
Mechanistic study of opposite migration order of dimethindene enantiomers in capillary electrophoresis in the presence of native β-cyclodextrin and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin

Chankvetadze, Bezhan and Pintore, Giorgio Antonio Mario and Burjanadze, Naira and Bergenthal, Dieter and Bergander, Klaus and Breitkreuz, Jörg (2000) Mechanistic study of opposite migration order of dimethindene enantiomers in capillary electrophoresis in the presence of native β-cyclodextrin and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin. Journal of Chromatography A, Vol. 875 (1-2), p. 455-469. ISSN 0021-9673. Article.

Full text not available from this repository.

DOI: 10.1016/S0021-9673(00)00146-1

Abstract

The possible mechanisms of the opposite affinity pattern of the enantiomers of dimethindene {(R,S)-N,N-dimethyl-3[1(2-pyridyl)ethyl]indene-2-ethylamine} (DIM) towards native β-cyclodextrin (β-CD) and heptakis(2,3,6-tri-O-methyl-)-β-CD (TM-β-CD) were studied using capillary electrophoresis (CE), NMR spectrometry, electrospray ionization mass spectrometry (ESI-MS) and X-ray crystallography. NMR spectrometry allowed to estimate the stoichiometry of the complex and to determine the binding constants. As found using ESI-MS, together with more abundant 1:1 complex, a complex with 1:2 stoichiometry may also be present in a rather small amount in a solution of DIM and β-CD. One-dimensional ROESY experiments indicated that the geometry of the complexes of DIM with native β-CD depends on the ratio of the components in the solution. In the 1:1 solution of DIM and β-CD the complex may be formed by inclusion of the indene moiety of DIM into the cavity of β-CD on the primary side and into the cavity of TM-β-CD into the secondary side. The most likely structural reason for lower affinity of the enantiomers of DIM towards the cavity of TM-β-CD compared to native β-CD could be elucidated. The indene moiety does not enter the cavity of TM-β-CD as deeply as the cavity of β-CD. This may be the most likely explanation of significantly higher affinity constants of DIM enantiomers towards the latter CD compared to the former one. The marked difference between the structure of the complexes may also be responsible for the opposite affinity pattern of the DIM enantiomers towards β-CD and TM-β-CD. Chankvetadze,1, , a, Giorgio Pintoreb, Naira Burjanadzea, Dieter Bergenthala, Klaus Berganderc, Jorg Breitkreuzd, Christoph Mühlenbrocka and Gottfried Blaschke

Item Type:Article
ID Code:4465
Status:Published
Refereed:Yes
Uncontrolled Keywords:Dimethindene, cyclodextrins
Subjects:Area 05 - Scienze biologiche > BIO/15 Biologia farmaceutica
Divisions:001 Università di Sassari > 01 Dipartimenti > Farmaco, chimico, tossicologico
Publisher:Elsevier Science
ISSN:0021-9673
Copyright Holders:© 2000 Elsevier Science B.V.
Deposited On:01 Sep 2010 15:41

I documenti depositati in UnissResearch sono protetti dalle leggi che regolano il diritto d'autore

Repository Staff Only: item control page