Investigation of Binding Behavior between Drug Molecule 5‐Fluoracil and M₄L₄‐Type Tetrahedral Cages: Selectivity, Capture, and Release

Abstract

Two analogous M L -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.

Anticancer Activity and Cisplatin Binding Ability of Bis-Quinoline and Bis-Isoquinoline Derived [Pd2L4]4+ Metallosupramolecular Cages

“…Inspired by the success of cisplatin and other metallodrugs (Mjos and Orvig, 2014 ) there is emerging interest in exploiting MSAs for biomedical purposes (Cook et al, 2013 ; Therrien, 2015 ; Casini et al, 2017 ; Zhou et al, 2017 ). Several groups have examined MSAs as drug delivery vectors (Therrien et al, 2008 ; Schmitt et al, 2012 ; Yi et al, 2012 ; Zheng et al, 2015 ; Samanta et al, 2016 , 2017 ; Bhat et al, 2017 ; Xu et al, 2017 ; Wang J.-F. et al, 2018 ; Yue et al, 2018 ). Additionally, MSAs have been shown to bind DNA (Oleksy et al, 2006 ; Garci et al, 2017 ; Zhao et al, 2017 ) and RNA (Phongtongpasuk et al, 2013 ; Malina et al, 2015 ), interact with proteins (Li et al, 2014 ; Mitchell et al, 2017 ) and have anticancer (Hotze et al, 2008 ; Faulkner et al, 2014 ; Grishagin et al, 2014 ; Dubey et al, 2015 ; Zheng et al, 2016 ; Allison et al, 2018 ) and antibacterial (Richards et al, 2009 ; Howson et al, 2012 ; Wang H. et al, 2018 ) properties.…”

Metal‐Organic Cages for Biomedical Applications

“…In 2017, Su group synthesized and investigated two analogous M 4 L 4 ‐type tetrahedral cages (smaller: MOC‐19 ; larger: MOC‐22 ) for their interactions with the anticancer drug 5‐FU, one of the broad‐spectrum anticancer drugs for malignancies such as glioblastoma and breast cancer . It turns out that 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.…”

Polymeric Systems Containing Supramolecular Coordination Complexes for Drug Delivery

“…For example, numerous two-dimensional (2D) metallacycles and three-dimensional (3D) metallacages with various functions have been synthesized through coordination-driven assemblies, and they have wide applications in catalysis, sensors, amphiphilic self-assembly, supramolecular polymers, host−guest chemistry, and drug delivery [15][16][17][18][19][20][21][22][23][24][25][26][27]. Moreover, SCC-based materials are potential candidates for drug delivery for to the following reasons: first, the unique cavities of SCCs facilitate drug transport owing to the SCC's hydrophobic property and adjustable size [28,29]. Second, the ingestion process of the drugs is realized by rationally designed SCC structures [30,31].…”