School of Pharmaceutical Sciences, University of Geneva, University of Lausanne, Quai Ernest Ansermet 30, 1211 Geneva, Switzerland; West University of Timisoara, Department of Biology-Chemistry, Pestalozzi 16, Timisoara 300115, Romania; West University of Timisoara, Advanced Environmental Research Laboratories, Oituz 4, Timisoara 300086, Romania.
University Hospital of Lausanne (CHUV-UNIL), Department of Musculoskeletal Medicine, EPCR/02/ch. Croisettes 22, 1066 Epalinges, Switzerland.
Carbohydr Polym. 2015 May 20;122:46-52. doi: 10.1016/j.carbpol.2014.12.014. Epub 2014 Dec 25.
We present here the synthesis of a highly O-carboxymethylated chitosan derivative. First, an improved protocol for the two-step synthesis of N-trimethyl chitosan (TMC) from chitosan was developed, yielding a maximum degree of quaternization (DQ) of up to 46.6%. Successively, the chitosan derivative O-carboxymethyl-N-trimethyl chitosan (CMTMC) was synthesized from the TMC obtained by applying an optimized synthesis pathway. In contrast to previous reports, the optimized protocol was shown to yield very high rates (>85%) of O-carboxymethylation of CMTMC, as shown by (1)H NMR and heteronuclear single quantum correlation ((1)H-(13)C HSQC). Finally, in vitro cytocompatibility (viability >80%) of the polymer was demonstrated using human fibroblasts.
我们在此介绍一种高度 O-羧甲基化壳聚糖衍生物的合成方法。首先，我们改进了两步法从壳聚糖制备 N-三甲基壳聚糖（TMC）的方法，得到的季铵化度（DQ）最高可达 46.6%。然后，我们从通过优化的合成途径获得的 TMC 合成了壳聚糖衍生物 O-羧甲基-N-三甲基壳聚糖（CMTMC）。与之前的报道相比，优化的方案显示出非常高的 CMTMC 的 O-羧甲基化率（>85%），这可以通过（1）H NMR 和异核单量子相关（1）H-（13）C HSQC 得到证明。最后，使用人成纤维细胞证明了该聚合物的体外细胞相容性（存活率>80%）。
