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

TitleInclusion excluded: Chiroptical sensing of the external surface of sulfated cyclodextrins.
Publication TypeJournal Article
Year of Publication2015
AuthorsZsila, F
JournalBiochem Biophys Res Commun
Volume460
Issue3
Pagination863-7
Date Published2015 May 8
ISSN1090-2104
KeywordsCircular Dichroism, Cyclodextrins, Optical Devices, Spectrophotometry, Ultraviolet, Stereoisomerism, Sulfates, Surface Properties
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 (K(a) ∼ 10(7) 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.

DOI10.1016/j.bbrc.2015.03.123
Alternate JournalBiochem. Biophys. Res. Commun.
PubMed ID25827814