Globular Carbohydrate Macromolecule “Sugar Balls” IV. Synthesis of Dendritic Nanocapsules with Molecular Recognition Sites on Periphery
Globular Carbohydrate Macromolecule “Sugar Balls” IV. Synthesis of Dendritic Nanocapsules with Molecular Recognition Sites on Periphery
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球状碳水化合物大分子“糖球”IV. 外围具有分子识别位点的树枝状纳米胶囊的合成
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发表时间：
1999
期刊：
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通讯作者：
M. Okada
中科院分区：
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作者：
K. Tsutsumiuchi;K. Aoi;M. Okada
摘要 8-苯胺基-1-萘磺酸钠盐 (ANS) 封装的 [O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-L-丝氨酸]-全取代聚酰胺基胺 (PAMAM) 树枝状聚合物（G=6.0、7.0 和 8.0）和 ANS 封装[O-(β-D-吡喃半乳糖基)-L-丝氨酸]-全取代PAMAM树枝状聚合物(G=7.0和8.0)是通过PAMAM树枝状聚合物与糖NCA之间的聚合物反应合成的(即O-(2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖基)-L-丝氨酸N-羧酸酐) (NCA) 和 O-(四-O-乙酰基-β-d-吡喃半乳糖基)-L-丝氨酸 NCA) 在 ANS 存在下于氯仿中进行，然后用甲醇中的一水合肼进行脱乙酰化。通过在碱性条件下对胶囊的水解产物进行定量UV分析来测定每个单(糖肽)型糖球胶囊的ANS分子数。结果表明，包封效率取决于糖残基的表面密度。胶囊的紫外和荧光分析以及凝胶过滤色谱表明ANS存在于单（糖肽）型糖球胶囊的相对中空的内腔中。小麦胚芽凝集素（WGA）凝集素血凝活性的抑制试验表明，该胶囊由于糖残基而具有高度特异性的分子识别能力。
Abstract8-Anilino-1-naphthalenesulfonic acid sodium salt (ANS)-encapsulated [O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-serine]-persubstituted poly(amido amine) (PAMAM) dendrimers (G=6.0, 7.0, and 8.0) and ANS-encapsulated [O-(β-D-galactopyranosyl)-L-serine]-persubstituted PAMAM dendrimers (G=7.0 and 8.0) were synthesized by polymer reaction between PAMAM dendrimers and glycoNCAs (i.e., O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine N-carboxyanhydride (NCA) and O-(tetra-O-acetyl-β-d-galactopyranosyl)-L-serine NCA) in the presence of ANS in chloroform, followed by deacetylation with hydrazine monohydrate in methanol. Number of ANS molecules per the mono(glycopeptide)-type sugar ball capsule was determined by quantitative UV analysis of the hydrolysis product of the capsule under a basic condition. The results suggested that the encapsulation efficiency depended on the surface density of sugar residues. UV and fluorescent analyses and gel filtration chromatography of the capsule indicated the existence of ANS in a relatively hollow internal cavity of the mono(glycopeptide)-type sugar ball capsule. An inhibition test of hemagglutinating activity of wheat germ agglutinin (WGA) lectin demonstrated that the capsule has a highly specific molecular recognition ability owing to the sugar residues.