Hybrid Molecular Container Based on Glycoluril and Triptycene: Synthesis, Binding Properties, and Triggered Release,Chemistry - A European Journal

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Hybrid Molecular Container Based on Glycoluril and Triptycene: Synthesis, Binding Properties, and Triggered Release
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2018-08-20 , DOI: 10.1002/chem.201802981
Wenjin Liu _{1,

2} , Xiaoyong Lu ₂ , Weijian Xue ₂ , Soumen K. Samanta ₂ , Peter Y. Zavalij ₂ , Zihui Meng ₁ , Lyle Isaacs ₂

Affiliation

We designed and synthesized a “hybrid” molecular container 1, which is structurally related to both cucurbit[n]uril (CB[n]) and pillar[n]arene type receptors. Receptor 1 was fully characterized by ¹H NMR, ¹³C NMR, IR, MS and X‐ray single crystal diffraction. The self‐association behavior, host–guest recognition properties of 1, and the [salt] dependence of K_a were investigated in detail by ¹H NMR and isothermal titration calorimetry (ITC). Optical transmittance and TEM measurements provide strong evidence that receptor 1 undergoes co‐assemble with amphiphilic guest C10 in water to form supramolecular bilayer vesicles (diameter 25.6±2.7 nm, wall thickness ≈3.5 nm) that can encapsulate the hydrophilic anticancer drug doxorubicin (DOX) and the hydrophobic dye Nile red (NR). The release of encapsulated DOX or NR from the vesicles can be triggered by hexamethonium (8 c) or spermine (10) which leads to the disruption of the supramolecular vesicles.

更新日期：2018-08-20

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