Département de Chimie, Université de Montréal , C.P. 6128, Succ. Centre-ville, Montreal, QC H3C 3J7, Canada.
School of Materials Science and Engineering, South China University of Technology , Guangzhou, China.
Biomacromolecules. 2017 Mar 13;18(3):778-786. doi: 10.1021/acs.biomac.6b01640. Epub 2017 Feb 24.
Natural compounds glucosamine and cholic acid have been used to make acrylic monomers which are subsequently used to prepare amphiphilic block copolymers by reversible addition-fragmentation chain transfer (RAFT) polymerization. Despite the striking difference in polarity and solubility, three diblock copolymers consisting of glucosamine and cholic acid pendants with different hydrophilic and hydrophobic chain lengths have been synthesized without the use of protecting groups. They are shown to self-assemble into polymeric micelles with a "bitter" bile acid core and "sweet" sugar shell in aqueous solutions, as evidenced by dynamic light scattering and transmission electron microscopy. The critical micelle concentration varies with the hydrophobic/hydrophilic ratio, ranging from 0.62 to 1.31 mg/L. Longer chains of polymers induced the formation of larger micelles in range of 50-70 nm. These micelles can solubilize hydrophobic compounds such as Nile Red in aqueous solutions. Their loading capacity mainly depends upon the hydrophobic/hydrophilic ratio of the polymers, and may be also related to the length of the hydrophilic block. These polymeric micelles allowed for a 10-fold increase in the aqueous solubility of paclitaxel and showed no cytotoxicity below the concentration of 500 mg/L. Such properties make these polymeric micelles interesting reservoirs for hydrophobic molecules and drugs for biomedical applications.
天然化合物葡萄糖胺和胆酸已被用于制备丙烯酰胺单体，随后通过可逆加成-断裂链转移（RAFT）聚合来制备两亲嵌段共聚物。尽管极性和溶解度有显著差异，但在不使用保护基团的情况下，仍成功合成了由葡萄糖胺和胆酸侧链组成的三种具有不同亲水性和疏水性链长的两嵌段共聚物。通过动态光散射和透射电子显微镜证实，它们在水溶液中自组装成具有“苦”胆酸核和“甜”糖壳的聚合物胶束。临界胶束浓度随疏水性/亲水性比值的变化而变化，范围为 0.62 至 1.31mg/L。聚合物长链诱导形成 50-70nm 的较大胶束。这些胶束可以在水溶液中溶解疏水性化合物，如尼罗红。其载药能力主要取决于聚合物的疏水性/亲水性比值，可能也与亲水链段的长度有关。这些聚合物胶束使紫杉醇在水中的溶解度提高了 10 倍，在 500mg/L 以下浓度时没有细胞毒性。这些特性使这些聚合物胶束成为生物医学应用中疏水分子和药物的有趣储库。
