Inclusion excluded: Chiroptical sensing of the external surface of sulfated cyclodextrins

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Abstract

It is shown that the heparin antagonist bis-aminoquinoline derivative surfen interacts with sulfated cyclodextrins in a unique fashion. Analysis of the UV spectroscopic data revealed exceptionally strong association (Ka ∼ 107 M-1) of several surfen molecules to the external surface of the cyclodextrin hosts. H-bonded to the sulfate groups in 1:1 stoichiometry, the drug molecules form a chiral layer around the macrocycles. Due to the steric proximity, dipole-dipole coupling occurs between the adjacent aminoquinoline rings that accounts for the large UV hypochromism and the induced exciton couplet in the circular dichroism spectra.

Original languageEnglish
Pages (from-to)863-867
Number of pages5
JournalBiochemical and biophysical research communications
Volume460
Issue number3
DOIs
Publication statusPublished - May 2 2015

Keywords

  • Circular dichroism
  • Exciton coupling
  • Hypochromism
  • Sulfated cyclodextrin
  • Surfen

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Molecular Biology
  • Cell Biology

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