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

Zsila, Ferenc (2015) Inclusion excluded: Chiroptical sensing of the external surface of sulfated cyclodextrins. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 460 (3). pp. 863-867. ISSN 0006-291X

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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.

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