Preparation of water-soluble glycopolymers derived from five-membered iminosugars
| Autor: | M.-Violante de-Paz, Macarena Martínez-Bailén, Elsa Galbis, Ana T. Carmona, Inmaculada Robina |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Polymers and Plastics Organic Chemistry General Physics and Astronomy 02 engineering and technology Oligosaccharide 010402 general chemistry 021001 nanoscience & nanotechnology Methacrylate 01 natural sciences Combinatorial chemistry Pyrrolidine 0104 chemical sciences chemistry.chemical_compound chemistry Materials Chemistry Copolymer Click chemistry Surface modification Reversible addition−fragmentation chain-transfer polymerization Mitsunobu reaction 0210 nano-technology |
| Zdroj: | European Polymer Journal. 119:213-221 |
| ISSN: | 0014-3057 |
| DOI: | 10.1016/j.eurpolymj.2019.07.027 |
| Popis: | Iminosugars are carbohydrate mimetics that constitute the main group of oligosaccharide processing enzyme inhibitors. They play an important role in cell-cell recognition processes, thereby presenting a wide range of potential therapeutic applications. In this work, we present the first examples of glycopolymers containing five-membered iminosugars. The preparation is carried out by constructing first a biocompatible water-soluble and pH-responsive 2-hydroxyethyl methacrylate (HEMA)-based copolymer by RAFT polymerization with an excellent control on the copolymer composition and low polydispersity (Mn = 19,800; Mw = 23,800; Mw/Mn = 1.2; experimental copolymer mole composition (by 1H NMR): pHEMA49%-co-pDMAEMA51%). One-pot azidation of its primary hydroxyl groups by Mitsunobu reaction led to a full functionalization of the HEMA residues. Subsequently, a selection of alkynyl pyrrolidine iminosugars showing glycosidase inhibition properties, were anchored to the functionalized azido-polymer through CuAAC click reaction furnishing successfully the aimed water-soluble glycopolymers, which were then subjected to biological evaluation as enzyme inhibitors. |
| Databáze: | OpenAIRE |
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