Sun He-Lue, Zhang Ying-Ming, Chen Yong, Liu Yu
Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P. R. China.
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin, 300071, P. R. China.
Sci Rep. 2016 Dec 23;6(1):27. doi: 10.1038/s41598-016-0026-z.
Ionizable cyclodextrins have attracted increasing attention in host-guest chemistry and pharmaceutical industry, mainly due to the introduction of favorable electrostatic interactions. The ionizable cyclodextrins could not only enhance its own solubility but also induce oppositely charged guests to form more stable complex. However, the aggregation induced by charged cyclodextrins has rarely been reported. In this work, guided by the concept of molecular-induced aggregation, a series of carboxyl modified cyclodextrins were synthesized via "click" and hydrolysis reaction. Then, UV-vis spectrum was used to investigate the aggregating behaviors induced by these cyclodextrins towards the cationic guest molecules. The results showed that only the hepta-carboxyl-β-cyclodextrin could induce the guest molecules to self-assemble into supramolecular spherical nanoparticles. Meanwhile, it could form stable inclusion complex with amantadine, a drug for anti-Parkinson and antiviral. The assembly behaviors were investigated by dynamic light scattering, scanning electron microscope, atomic force microscope, transmission electron microscope and NMR spectroscopy. The supramolecular nanoparticles induced by hepta-carboxyl-β-CD and its inclusion with amantadine could be used to encapsulate the model drug and achieve its controlled releasing behaviors.
可离子化环糊精在主客体化学和制药工业中受到越来越多的关注，主要是由于引入了有利的静电相互作用。可离子化环糊精不仅可以提高自身的溶解度，还能诱导带相反电荷的客体形成更稳定的复合物。然而，关于带电荷环糊精诱导的聚集现象鲜有报道。在这项工作中，以分子诱导聚集的概念为指导，通过“点击”反应和水解反应合成了一系列羧基修饰的环糊精。然后，利用紫外可见光谱研究了这些环糊精对阳离子客体分子的聚集行为。结果表明，只有七羧基-β-环糊精能诱导客体分子自组装成超分子球形纳米颗粒。同时，它能与抗帕金森和抗病毒药物金刚烷形成稳定的包合物。通过动态光散射、扫描电子显微镜、原子力显微镜、透射电子显微镜和核磁共振光谱对组装行为进行了研究。七羧基-β-环糊精诱导形成的超分子纳米颗粒及其与金刚烷的包合物可用于包封模型药物并实现其控释行为。
