A fluorescent calixarene-based dimeric capsule constructed via a M-II-terpyridine interaction: cage structure, inclusion properties and drug release

摘要

Two analogues of capsule-like fluorescent cages have been constructed by dimerization of terpyridine-containing calixarene derivatives utilizing a M-II-terpyridine (M = Zn and Cd) interaction. H-1 NMR spectral studies show that the self-assembled molecular capsules Zn(4)L1(2) and Cd(4)L1(2) have a highly symmetrical D-4h-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- and - 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 Zn(4)L1(2) cages for drug-carrier applications.