Cyclodextrin-Adamantane Host鈥揋uest Interactions on the Surface of Biocompatible Adamantyl-Modified Glycodendrimers

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• 作者：Marco Paolino ; Franka Ennen ; Stefania Lamponi ; Mihaela Cernescu ; Brigitte Voit ; Andrea Cappelli ; Dietmar Appelhans ; Hartmut Komber
• 刊名：Macromolecules
• 出版年：2013
• 出版时间：May 14, 2013
• 年：2013
• 卷：46
• 期：9
• 页码：3215-3227
• 全文大小：629K
• 年卷期：v.46,no.9(May 14, 2013)
• ISSN：1520-5835

文摘

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 尾-cyclodextrin (尾-CD). Glycosylated fourth generation PPIs showing an average substitution in adamantyl groups of 13% were found to interact with 尾-CD effectively, and were considered as candidates for further complexation studies with a polymeric cyclodextrin derivative (poly-尾-CD). The host鈥揼uest 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.