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通过甲磺酰化和区域选择性 Cu(I)催化环加成合成壳聚糖-PEO 水凝胶。

Synthesis of chitosan-PEO hydrogels via mesylation and regioselective Cu(I)-catalyzed cycloaddition.

机构信息

Institute for Polymers, Composites and Biomaterials, CNR, Via Campi Flegrei 34, 80078 Pozzuoli (Naples), Italy.

Department of Chemistry "Paolo Corradini", University of Naples "Federico II", Via Cinthia, Naples, Italy.

出版信息

Carbohydr Polym. 2014 Nov 4;112:736-45. doi: 10.1016/j.carbpol.2014.06.026. Epub 2014 Jun 18.

DOI:10.1016/j.carbpol.2014.06.026
PMID:25129803
Abstract

In this work, a well-defined hydrogel was developed by coupling chitosan with PEO through "click chemistry". Azide functionalities were introduced onto chitosan, through mesylation of C-6 hydroxyl groups, and reacted with a di-alkyne PEO by a regioselective Cu(I)-catalyzed cycloaddition. This synthetic approach allowed us to obtain a hydrogel with a controlled crosslinking degree. In fact, the extent of coupling is strictly dependent on the amount of azido groups on chitosan, which in turn can be easily modulated. The obtained hydrogel, with a crosslinking degree of around 90%, showed interesting swelling properties. With respect to chitosan hydrogels reported in literature, a considerably higher equilibrium uptake was reached (940%). The possibility to control the crosslinking degree of hydrogel and its capability to rapidly absorb high amounts of water make this material suitable for several applications, such as controlled drug release and wound healing.

摘要

在这项工作中,通过“点击化学”将壳聚糖与 PEO 偶联,开发出一种结构明确的水凝胶。通过 C-6 羟基的甲磺酸酯化,在壳聚糖上引入叠氮基团,并通过区域选择性 Cu(I)催化的环加成与二炔 PEO 反应。这种合成方法使我们能够获得具有受控交联度的水凝胶。实际上,偶联的程度严格取决于壳聚糖上叠氮基团的数量,而这又可以很容易地进行调节。所得到的水凝胶的交联度约为 90%,表现出有趣的溶胀性能。与文献中报道的壳聚糖水凝胶相比,达到了更高的平衡吸水量(940%)。控制水凝胶交联度的可能性及其快速吸收大量水的能力使这种材料适用于多种应用,如控制药物释放和伤口愈合。

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