A fluorescent calixarene-based dimeric capsule constructed via a M(II)-terpyridine interaction: cage structure, inclusion properties and drug release.
A fluorescent calixarene-based dimeric capsule constructed via a M(II)-terpyridine interaction: cage structure, inclusion properties and drug release.
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DOI：
10.1039/c8ra02146e
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发表时间：
2018-06-19
期刊：
影响因子：
3.9
通讯作者：
Su, Cheng-Yong
中科院分区：
文献类型：
--
作者：
Wang, Jun-Fang;Huang, Li-Yuan;Bu, Jian-Hua;Li, Shao-Yong;Qin, Su;Xu, Yao-Wei;Liu, Jun-Min;Su, Cheng-Yong
利用联吡啶(M=Zn和Cd)的相互作用，通过联吡啶与杯芳烃的二聚反应，合成了两种类似的胶囊状荧光笼。~1H核磁共振波谱研究表明，自组装分子胶囊Zn4L12和Cd4L12具有高度对称的D4H结构。核磁共振、电喷雾飞行时间质谱仪、荧光开关和分子模拟等方法证实了抗癌药物硫代嘌呤在其空腔中的包封性，表明药物与CAGE之间强烈的S-π和π-π相互作用对主客体结合具有重要意义。纳米笼子在pH=7.4的磷酸盐缓冲盐水溶液中表现出良好的控制硫代嘌呤释放的行为。这些结果进一步突出了自组装的Zn4L12笼在药物载体应用中的潜力。基于杯芳烃的荧光二聚体胶囊通过三联吡啶相互作用构建，可以捕获溶液和结晶态的硫代嘌呤，并控制药物在PBS中的释放，并伴随着荧光恢复。
Two analogues of capsule-like fluorescent cages have been constructed by dimerization of terpyridine-containing calixarene derivatives utilizing a MII–terpyridine (M = Zn and Cd) interaction. 1H NMR spectral studies show that the self-assembled molecular capsules Zn4L12 and Cd4L12 have a highly symmetrical D4h-structure. The encapsulation of the anticancer drug mercaptopurine in their cavities has been documented by NMR, ESI-TOF-MS, fluorescence switching, and molecular simulation, indicating that strong S–π and π–π interactions between drug and cage are of importance for the host–guest binding. The nanoscale cages exhibit excellent behaviors to control the release of mercaptopurine in phosphate buffered saline solution (pH = 7.4). These results further highlight the potential of self-assembled Zn4L12 cages for drug-carrier applications. A fluorescent calixarene-based dimeric capsule has been constructed via a MII–terpyridine interaction, and can capture mercaptopurine in solution and crystalline state and control drug release in PBS accompanied with fluorescence recovery.
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