Abeylath Sampath C, Turos Edward
Center for Molecular Diversity in Drug Design, Discovery, and Delivery, Department of Chemistry, CHE 207, 4202 East Fowler Avenue, University of South Florida, Tampa, FL 33620, USA.
Carbohydr Polym. 2007 Aug 2;70(1):32-37. doi: 10.1016/j.carbpol.2007.02.027.
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-alpha-D-glucofuranose, 1-O-acryloyl-2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranose, 6-O-acryloyl-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose, 2-N-acryloyl-1,3,4,6-tetra-O-acetyl-beta-D-glucosamine, 5-O-acryloyl-2,3-isopropylidene-1-methoxy-beta-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-beta-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.
通过在水介质中进行自由基引发的乳液聚合反应，制备了一系列糖基化聚丙烯酸酯纳米颗粒。以丙烯酸乙酯作为共聚单体，将碳水化合物丙烯酸酯引入到聚（丙烯酸乙酯）骨架中，得到了平均粒径约为40 nm的稳定糖纳米颗粒乳液。利用该技术，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 - 二 - O - 异亚丙基 - α - D - 甘露糖呋喃糖、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 - 葡萄糖胺、5 - O - 丙烯酰基 - 2,3 - 异亚丙基 - 1 - 甲氧基 - β - D - 核糖呋喃糖和4 - N - 乙酰基 - 5'- O - 丙烯酰基 - 2',3'- O - 异亚丙基胞苷制备了多种糖纳米颗粒。乳液的扫描电子显微镜、动态光散射和质子核磁共振分析表明，除了O - 苄基和O - 苯甲酰基保护的碳水化合物丙烯酸酯的掺入不完全外，碳水化合物丙烯酸酯单体基本上100%掺入到聚合物中。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 - 核糖呋喃糖形成约80nm的较大糖纳米颗粒，揭示了单体中游离羟基在聚合过程中对粒径的影响，这一特征显然也取决于基质中碳水化合物的含量。这种方法为合成具有靶向药物递送和材料开发潜在应用的聚合物糖纳米颗粒提供了一种新的、简单的途径。
