Hybrid Molecular Container Based on Glycoluril and Triptycene: Synthesis, Binding Properties, and Triggered Release
Hybrid Molecular Container Based on Glycoluril and Triptycene: Synthesis, Binding Properties, and Triggered Release
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基于甘脲和三蝶烯的混合分子容器：合成、结合特性和触发释放
DOI：
10.1002/chem.201802981
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发表时间：
2018-09-20
影响因子：
4.3
通讯作者：
Isaacs, Lyle
中科院分区：
文献类型：
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作者：
Liu, Wenjin;Lu, Xiaoyong;Isaacs, Lyle
我们设计并合成了一个与葫芦[n]脲（CB[n]）和柱[n]芳烃型受体结构相关的杂化分子容器1。受体1经HNMR-H-1、CNMR-C-13、IR、MS和X-射线单晶衍射进行了表征。通过核磁共振氢谱（HNMR）-H-1和等温滴定量热法（ITC）详细研究了1的自缔合行为、主客体识别性质和K-a的[盐]依赖性。通过透射电镜和透射电镜的研究，证明受体1与两亲性客体C10在水中共组装形成了直径为25.6 ± 2.7nm，壁厚约3.5nm的双层超分子囊泡，并将亲水性抗癌药物阿霉素（DOX）和疏水性染料尼罗红（NR）包裹在囊泡中。包封的DOX或NR从囊泡中的释放可以由六烃季铵（8 c）或精胺（10）触发，这导致超分子囊泡的破坏。
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 (HNMR)-H-1, (CNMR)-C-13, 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 (HNMR)-H-1 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 +/- 2.7nm, wall thickness approximate to 3.5nm) 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 (8c) or spermine (10) which leads to the disruption of the supramolecular vesicles.