Authors Paolino, M. ; Ennen, F. ; Lamponi, S. ; Cernescu, M. ; Voit, B. ; Cappelli, A. ; Appelhans, D. ; Komber, H.
Title Cyclodextrin-adamantane host-guest interactions on the surface of biocompatible adamantyl-modified glycodendrimers
Date 14.05.2013
Number 37642
Abstract A series of adamantyl-modified glycodendrimers (mPPI-Gx-AdaA-C) was prepared in a two-step synthesis using two efficient reactions: (1) urea bond formation from amine and isocyanate and (2) reductive amination. 1H NMR spectroscopy (host guest titration and ROESY experiments) was used to evaluate the graded effect of steric hindrance as a function of the number and type of oligosaccharide molecules and of the number of adamantyl (Ada) units on the complexation with monomeric ß-cyclodextrin (ß-CD). Glycosylated fourth generation PPIs showing an average substitution in adamantyl groups of 13% were found to interact with ß-CD effectively, and were considered as candidates for further complexation studies with a polymeric cyclodextrin derivative (poly-ß-CD). The host–guest interaction features of the maltosylated dense shell glycodendrimer along with the low cytotoxicity provided the rational basis for the use of these adamantyl-functionalized glycodendrimers in the design of supramolecular systems potentially useful as healthcare materials.
Publisher Macromolecules
Citation Macromolecules 46 (2013) 3215-3227
Tags poly(propylene imine) dendrimers beta-cyclodextrin supramolecular polymers hydrophobic molecules starburst dendrimers inclusion complexes in-vivo water nanoparticles size

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