Selective binding of chiral molecules of cinchona alkaloid by β- and γ-cyclodextrins and organoselenium-bridged bis(β-cyclodextrin)s

Yu Liu, Li Li, Heng Yi Zhang, Zhi Fan, Xu Dong Guan

Research output: Contribution to journalArticle

Abstract

The inclusion complexation behavior of chiral members of cinchona alkaloid with β- and γ-cyclodextrins (1 and 2) and 6,6′-trimethylenediseleno-bridged bis(β-cyclodextrin) (3) was assessed by means of fluorescence and 2D-NMR spectroscopy. The spectrofluorometric titrations have been performed in aqueous buffer solution (pH 7.20) at 25.0°C to determine the stability constants of the inclusion complexation of 1-3 with guest molecules (i.e., cinchonine, cinchonidine, quinine, and quinidine) in order to quantitatively investigate the molecular selective binding ability. The stability constants of the resulting complexes of 2 with guest molecules are larger than that of 1. As a result of cooperative binding, the stability constants of inclusion complexation of dimeric β-cyclodextrin 3 with cinchonidine and cinchonine are higher than that of parent 1 by factor of 4.5 and 2.4, respectively. These results are discussed from the viewpoint of the size-fit and geometric complementary relationship between the host and guest.

Original languageEnglish (US)
Pages (from-to)11-23
Number of pages13
JournalBioorganic Chemistry
Volume31
Issue number1
DOIs
StatePublished - Feb 2003
Externally publishedYes

Keywords

  • 2D-NMR
  • Chiral molecule
  • Cinchona alkaloid
  • Cooperative binding
  • Cyclodextrins
  • Fluorescence
  • Inclusion complexation
  • Molecular recognition
  • Organoselenium
  • Stability constants

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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