title: Chiral recognition of verapamil by cyclodextrins studied with capillary electrophoresis, NMR spectroscopy, and electrospray ionization mass spectrometry.
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 beta-cyclodextrin (beta-CD) and heptakis(2,3, 6-tri-O-methyl)-beta-CD (TM-beta-CD). In addition, in the presence of beta-CD in the background electrolyte, longer migration times and lower separation factors were observed compared to TM-beta-CD. The binding constants of (+)- and (-)-VP with beta-CD and TM-beta-CD determined using (13)C 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.
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Münster, Hittorfstrasse 58-62, 48149 Münster, Germany.
authors.forename: B
authors.initials: B
authors.lastname: Chankvetadze
authors.forename: N
authors.initials: N
authors.lastname: Burjanadze
authors.forename: G
authors.initials: G
authors.lastname: Pintore
authors.forename: D
authors.initials: D
authors.lastname: Strickmann
authors.forename: D
authors.initials: D
authors.lastname: Bergenthal
authors.forename: G
authors.initials: G
authors.lastname: Blaschke
mesh_terms: D002121:Calcium Channel Blockers / Q000737:chemistry*; D003505:Cyclodextrins / Q000494:pharmacology*; D019075:Electrophoresis, Capillary; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013237:Stereoisomerism; D014700:Verapamil / Q000032:analysis / Q000737:chemistry*; D047392:beta-Cyclodextrins
chemical_list: D002121:Calcium Channel Blockers; D003505:Cyclodextrins; D047392:beta-Cyclodextrins; D014700:Verapamil; C031215:betadex