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Chiral recognition of verapamil by cyclodextrins studied with capillary electrophoresis, NMR spectroscopy, and electrospray ionization mass spectrometry

Chankvetadze, Bezhan and Burjanadze, Naira and Pintore, Giorgio Antonio Mario and Strickmann, Dirk and Bergenthal, Dieter and Blaschke, Gottfried (1999) Chiral recognition of verapamil by cyclodextrins studied with capillary electrophoresis, NMR spectroscopy, and electrospray ionization mass spectrometry. Chirality, Vol. 11 (8), p. 635-644. eISSN 1520-636X. Article.

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DOI: 10.1002/(SICI)1520-636X(1999)11:8<635::AID-CHIR5>3.0.CO;2-D

Abstract

Capillary electrophoresis (CE) allows the observation of the opposite affinities of the enantiomers of (±)-verapamil [2-isopropyl-2,8-bis(3,4-dimethoxyphenyl)-6-methyl-6-azaoctannitrile, VP] toward β-cyclodextrin (β-CD) and heptakis(2,3,6-tri-O-methyl)- β-CD (TM-β-CD). In addition, in the presence of β-CD in the background electrolyte, longer migration times and lower separation factors were observed compared to TM-β-CD. The binding constants of (+)- and (−)-VP with β-CD and TM-β-CD determined using 13C NMR spectroscopy explain the results observed in CE. Electrospray ionization mass spectrometry (ESI-MS) was used as an alternative technique for the characterization of VP-CD complexes.

Item Type:Article
ID Code:4472
Status:Published
Refereed:Yes
Uncontrolled Keywords:Chiral CE, NMR spectroscopy, ESI-MS, cyclodextrins, (±)-verapamil/cyclodextrin complexes, stoichiometry, binding constants
Subjects:Area 05 - Scienze biologiche > BIO/15 Biologia farmaceutica
Divisions:001 Università di Sassari > 01 Dipartimenti > Farmaco, chimico, tossicologico
Publisher:Wiley-Liss
eISSN:1520-636X
Deposited On:02 Sep 2010 12:43

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