Solution-to-Surface Molecular-Delivery System Using a Macrocyclic Sugar Cluster. Sugar-Directed Adsorption of Guests in Water on Polar Solid Surfaces
Solution-to-Surface Molecular-Delivery System Using a Macrocyclic Sugar Cluster. Sugar-Directed Adsorption of Guests in Water on Polar Solid Surfaces
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使用大环糖簇的溶液到表面分子递送系统。
DOI：
10.1021/ja9709536
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发表时间：
1997
影响因子：
15
通讯作者：
Y. Aoyama
中科院分区：
文献类型：
--
作者：
T. Fujimoto;Chikao Shimizu;O. Hayashida;Y. Aoyama
细胞表面寡糖以簇的形式存在。它们在各种细胞识别过程中发挥重要作用，其中糖-受体相互作用通常被认为是多价的。2所谓的簇效应2已经导致许多工作者研究各种多触角合成糖衍生物（聚合物和低聚物，3树枝状聚合物，4表面活性剂聚集体，5和金属络合物6）的受体结合特性。本工作涉及一个明确的大环糖簇与非生物极性固体表面作为一个简化的多价受体位点的相互作用。我们在这里报告，在水中的聚类糖部分可以不可逆地吸附或组装在二氧化硅表面上。再加上作为宿主的大环的客体结合能力，这导致了一种新的糖导向的溶液至表面的分子递送系统。7以杯[4]间苯二酚（1f; R）（CH 2）10 CH 3）8为原料，经四步反应制得八胺1 e，再与内酯（2）反应制得杯[4]间苯二酚的八乳糖衍生物。化合物If高度溶于水（> 0.1M）。然而，它很容易吸附在石英板（石英玻璃）的表面浸渍在前者的水溶液。10回收的印版10的电子吸收光谱表明了以下情况。(1)的
Cell-surface oligosaccharides occur as clusters. They play essential roles in various cell-recognition processes, 1 where saccharide-receptor interactions are often claimed to be multivalent. 2 The so-called cluster effect2 has led many workers to investigate the receptor-binding properties of a variety of multiantennal synthetic saccharide derivatives (polymers and oligomers, 3 dendrimers, 4 surfactant aggregates, 5 and metal complexes6). The present work is concerned with the interaction of a well-defined macrocyclic sugar cluster with a nonbiological polar solid surface as a simplified multivalent receptor site. We report here that the clustering sugar moieties in water can be irreversibly adsorbed or assembled on the silica surface. Coupled with the guest-binding ability of the macrocycle as a host, this leads to a novel sugar-directed solution-to-surface molecular delivery system. 7An octagalactose derivative of calix [4] resorcarene (1f; R)(CH2) 10CH3) 8 was obtained by the reaction of lactonolactone (2) with octaamine 1e, which was prepared in four steps from the parent macrocycle 1a. 9 Compound 1f is highly soluble in water (> 0.1 M). Nevertheless, it is readily adsorbed on the surface of quartz plate (silica glass) dipped in an aqueous solution of the former. 10 Electronic absorption spectroscopy for the recovered plates10 indicates the following.(1) The