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

✍ Scribed by Bezhan Chankvetadze; Naira Burjanadze; Giorgio Pintore; Dirk Strickmann; Dieter Bergenthal; Gottfried Blaschke

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 297 KB
• Volume: 11
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/(sici)1520-636x(1999)11:8<635::aid-chir5>3.0.co;2-d

✦ Synopsis

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 ␤-cyclodextrin (␤-CD) and heptakis(2,3,6-tri-Omethyl)-␤-CD (TM-␤-CD). In addition, in the presence of ␤-CD in the background electrolyte, longer migration times and lower separation factors were observed compared to TM-␤-CD. The binding constants of (+)-and (-)-VP with ␤-CD and TM-␤-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. Chirality 11:635-644, 1999.