Issue 40, 2018

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

Abstract

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.

Graphical abstract: A fluorescent calixarene-based dimeric capsule constructed via a MII–terpyridine interaction: cage structure, inclusion properties and drug release

Supplementary files

Article information

Article type
Paper
Submitted
11 Cig 2018
Accepted
08 Qas 2018
First published
20 Qas 2018
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2018,8, 22530-22535

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

J. Wang, L. Huang, J. Bu, S. Li, S. Qin, Y. Xu, J. Liu and C. Su, RSC Adv., 2018, 8, 22530 DOI: 10.1039/C8RA02146E

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