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Glycosylated polyacrylate nanoparticles by emulsion polymerization

机译：乳液聚合制备糖基化聚丙烯酸酯纳米颗粒

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A selection of glycosylated polyacrylate nanoparticles has been prepared by radical-initiated emulsion polymerization in aqueous media. Using ethyl acrylate as a co-monomer, carbohydrate acrylates were incorporated into the poly(ethyl acrylate) framework to give stable emulsions of glyconanoparticles with an average particle size of around 40 nm. Using this technique a variety of glyconanoparticles were prepared from 3-O-acryloyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, 1-O-acryloyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose, 6-O-acryloyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose, 2-N-acryloyl-1,3,4,6-tetra-O-acetyl-β-D-glucosamine, 5-O-acryloyl-2,3-isopropylidene-1-methoxy-β-D-ribofuranose and 4-N-acetyl-5’-O-acryloyl-2’,3’-O-isopropylidene cytidine. Scanning electron microscopy, dynamic light scattering and proton NMR analysis of the emulsions indicated essentially 100% incorporation of the carbohydrate acrylate monomer into the polymer with the exception of O-benzyl- and O-benzoyl-protected carbohydrate acrylates, which gave incomplete incorporation. Formation of larger glyconanoparticles of ~80nm with (unprotected) 3-O-acryloyl-D-glucose and 5-O-acryloyl-1-methoxy-β-D-ribofuranose revealed the influence of free hydroxyl groups in the monomer on the particle size during polymerization, a feature which is also apparently dependent on the amount of carbohydrate in the matrix. This methodology allows for a new, simple route to the synthesis of polymeric glyconanoparticles with potential applications in targeted drug delivery and materials development.
机译：通过在水性介质中自由基引发的乳液聚合反应，已经制备了一些糖基化聚丙烯酸酯纳米颗粒。使用丙烯酸乙酯作为共聚单体，将碳水化合物丙烯酸酯掺入聚（丙烯酸乙酯）骨架中，以得到平均粒径约为40nm的稳定的糖纳米颗粒乳液。使用该技术，由3-O-丙烯酰基-1,2：5,6-二-O-异亚丙基-α-D-葡萄糖呋喃糖，1-O-丙烯酰基-2,3：5,6-制备了多种糖纳米颗粒。二-O-异亚丙基-α-D-呋喃呋喃糖，6-O-丙烯酰基-1,2：3,4-二-O-异亚丙基-α-D-吡喃半乳糖，2-N-丙烯酰基-1,3,4， 6-四-O-乙酰基-β-D-葡糖胺，5-O-丙烯酰基-2,3-异亚丙基-1-甲氧基-β-D-核呋喃糖和4-N-乙酰基-5'-O-丙烯酰基-2 '，3'-O-异亚丙基胞苷。乳液的扫描电子显微镜，动态光散射和质子NMR分析表明，除了O-苄基和O-苯甲酰基保护的碳水化合物丙烯酸酯外，碳水化合物丙烯酸酯单体基本100％掺入聚合物中，这导致掺入不完全。用（未保护的）3-O-丙烯酰基-D-葡萄糖和5-O-丙烯酰基-1-甲氧基-β-D-呋喃呋喃糖形成〜80nm的较大糖纳米颗粒，揭示了单体中游离羟基对粒径的影响在聚合过程中，其特征显然也取决于基质中碳水化合物的量。这种方法学为合成聚合物糖纳米颗粒提供了一条新的简单途径，在靶向药物输送和材料开发中具有潜在的应用前景。

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