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. 2017 Mar 13;23(15):3542-3547.
doi: 10.1002/chem.201606060. Epub 2017 Feb 9.

Investigation of Binding Behavior between Drug Molecule 5-Fluoracil and M4 L4 -Type Tetrahedral Cages: Selectivity, Capture, and Release

Wei-Qin Xu  1   2 , Yan-Zhong Fan  1 , Hai-Ping Wang  1 , Jun Teng  1 , Yu-Hao Li  1 , Cheng-Xia Chen  1 , Dieter Fenske  1 , Ji-Jun Jiang  1 , Cheng-Yong Su  1
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Investigation of Binding Behavior between Drug Molecule 5-Fluoracil and M4 L4 -Type Tetrahedral Cages: Selectivity, Capture, and Release

Wei-Qin Xu et al. Chemistry. .

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Abstract

Two analogous M4 L4 -type tetrahedral cages (smaller: MOC-19; larger: MOC-22) were synthesized and investigated for their interactions with the anticancer drug 5-fluoracil (5-FU) by NMR spectroscopy, high-resolution electrospray-ionization mass spectrometry (HR-ESI-MS), and molecular simulation. The cage's size and window are of importance for the host-guest binding, and consequently the smaller MOC-19 with a more suitable size of cavity window was found to have much stronger hydrogen-bond interactions with 5-FU. The porous nanoparticles of MOC-19 exhibited outstanding behavior for the controlled release of 5-FU in a simulated human body with liquid phosphate-buffered saline solution.

Keywords: 5-fluoracil; cage compound; controlled release; selective capture; structural conversion.

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