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目的制备具有主动肝靶向作用的低分子量半乳糖化脂肪酰壳聚糖聚合物胶束材料并进行结构表征,对其形成的胶束特性进行研究。方法以甲磺酸为溶剂及反应介质,利用脂肪酰氯(棕榈酰氯及月桂酰氯)与壳聚糖的OH进行酰化反应制备具有不同碳链长度及取代度的脂肪酰壳聚糖,再利用EDC.HCl活化乳糖酸,与所得的脂肪酰壳聚糖的2位氨基反应制备半乳糖化脂肪酰壳聚糖。用红外光谱、1H核磁共振谱对其结构进行表征及取代度的计算,并考察其溶解性能;制备其聚合物胶束,测定临界胶束浓度(CMC)和粒径。结果壳聚糖脂肪酰化的反应条件为20℃、1 h,半乳糖化反应的条件为30℃、24 h;壳聚糖棕榈酰化及月桂酰化反应中酰氯/壳聚糖的合适摩尔比分别为2∶1～8∶1、2∶1～10∶1。此条件下制得的脂肪酰壳聚糖及半乳糖化脂肪酰壳聚糖在二甲基亚砜(DMSO)中有较好的溶解性能;红外光谱、1H核磁共振光谱结果表明,成功合成了半乳糖化脂肪酰壳聚糖;脂肪酰基的取代度范围为0.28～1.13 mol,胶束的CMC约为0.39×10 2～2.82×10 2mg·mL-1,粒径大小119.8～546.0 nm。结论成功制备低分子量半乳糖化脂肪酰壳聚糖聚合物胶束材料。相同碳链长度条件下,脂肪酰氯与壳聚糖摩尔比越大,脂肪酰基的取代度越大,所得胶束的CMC及粒径越小;相同脂肪酰氯与壳聚糖摩尔比时,制得的半乳糖化脂肪酰壳聚糖的粒径小于脂肪酰壳聚糖的粒径。
OBJECTIVE: To prepare low molecular weight galacto-oligosaccharide chitosan polymer micelles with active liver-targeting effect and to characterize the structure of micelles. Methods Methanesulfonic acid was used as solvent and reaction medium. Fatty acid chitosan with different carbon chain length and degree of substitution was prepared by acylation of fatty acid chloride (palmitoyl chloride and lauroyl chloride) with OH of chitosan. EDC .HCl activates lactobionic acid to react with the amino group at the 2-position of the resulting fatty acid chitosan to produce galactosyl fatty acyl chitosan. Its structure was characterized by FTIR and 1H nuclear magnetic resonance spectroscopy, and its solubility was calculated. The polymer micelles were prepared and the critical micelle concentration (CMC) and particle size were determined. Results The reaction conditions for the fatty acylation of chitosan were 20 ℃ for 1 h and the conditions for the galactosylation reaction were 30 ℃ for 24 h. The suitable molar ratio of acid chloride / chitosan in the palmitoylation and lauroylation of chitosan 2: 1 to 8: 1, 2: 1 to 10: 1, respectively. Under these conditions, the fatty acyl chitosan and galactosyl fatty acyl chitosan have better solubility in dimethyl sulfoxide (DMSO). The results of IR and 1H nuclear magnetic resonance show that the The degree of substitution of fatty acyl group ranged from 0.28 to 1.13 mol, the CMC of micelles ranged from 0.39 × 10 2 to 2.82 × 10 2 mg · mL -1, and the size ranged from 119.8 to 546.0 nm. Conclusion Low molecular weight galactosyl fatty chitosan polymer micelles materials were successfully prepared. Under the same carbon chain length, the larger the molar ratio of fatty acid chloride to chitosan, the greater the degree of substitution of fatty acyl groups, the smaller the CMC and particle size of the resulting micelles. When the molar ratio of fatty acid chloride to chitosan is the same, Of the galactosyl fatty acid chitosan has a particle size smaller than that of the fatty acid chitosan.