T. Kikuchi et al., Synthesis of bis dansyl-modified beta-cyclodextrin liner trimer having multi-recognition sites and high hydrophobic environment, TETRAHEDRON, 57(45), 2001, pp. 9317-9324
Fluorescent beta -cyclodextrin (CyD) trimer linked with amine, which are (6
(A),6(D) -bis-deoxy-dansylamino-beta -CyD)6-deoxy-bis-beta -CyDs (beta -1),
has been synthesized in order to investigate their sensing ability for org
anic compounds such as bile acids. Host beta -1 showed pure monomer fluores
cence, exhibiting a decrement in fluorescence intensity on complexation of
bile acid. The extent of fluorescence variation with a guest was employed t
o evaluate the sensing ability of beta -1. The guest-induced variation in t
he fluorescence (Al) was used to describe the sensing ability of beta -1. H
ost beta -1 could detect ursodeoxycholic acid and chenodeoxycholic acid wit
h remarkable sensitivities, although, could not detect deoxycholic acid and
cholic acid. The behaviors of the appended moieties of beta -1 during a ho
st-guest complexation were studied by induced circular dichroism. (ICD), fl
uorescence and absorption spectra and MM2-energy-minimized structure. The g
uest-induced variations in the absorption, fluorescence, and ICD intensity
suggest that the appended moieties work as a hydrophobic cap to elevate bin
ding ability, and this fact was supported by three-dimension MM2-minimized
structure while a host-guest complexation occurred. (C) 2001 Elsevier Scien
ce Ltd. All rights reserved.