2-O-acryloyloxyethyl-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside) | 634589-71-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-O-acryloyloxyethyl-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside)
• 英文别名: 2-O-acryloyloxyethyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；2-(2',3',4',6'-tetra-O-acetyl-β-D-galactosyloxy)ethyl acrylate；(2-O-acryloyl)2-hydroxyethyl 2,3,4,6-tetra-O-acetyl beta-D-galactopyranoside；2-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyethyl prop-2-enoate
• CAS: 634589-71-2
• 化学式: C₁₉H₂₆O₁₂
• 分子量: 446.408
• InChiKey: XGCVASALBGQZAE-QFACEVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  31
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  丙烯酸羟乙酯 、 beta-D-半乳糖五乙酸酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以50.1%的产率得到2-O-acryloyloxyethyl-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside)
  参考文献：
  名称：

  Synthesis and pH/sugar/salt-sensitivity study of boronate crosslinked glycopolymer nanoparticles

  摘要：

  通过可逆加成片段链转移（RAFT）聚合和原子转移自由基聚合（ATRP）分别成功制备了聚（3-甲基丙烯酰胺基苯基硼酸）均聚物和聚（乙二醇）-嵌段-聚（2-丙烯酰氧基乙基-半乳糖）（PEG-b-PAEG）聚糖。动态光散射（DLS）、热分析和基于茜素红 S（ARS）的比色法和荧光测定证实了基于 PMAPBA 和 PEG-b-PAEG 复合物的硼酸盐交联纳米粒子的形成。纳米颗粒对 pH 值、盐和糖的敏感性很高。在 pH 值为 5.0 和 6.0 时，纳米颗粒出现聚集和沉淀。当 pH 值从 7 升至 11 时，粒径明显增大。在 pH 值为 10 时，纳米粒子对葡萄糖、半乳糖、甘露糖和蔗糖表现出明显的敏感性。由于带负电荷的苯硼酸基团的屏蔽作用，随着盐浓度的增加，硼酸盐交联纳米粒子出现了聚集现象。

  DOI：

  10.1039/c2nj40998d

文献信息

• Synthesis and pH/sugar/salt-sensitivity study of boronate crosslinked glycopolymer nanoparticles
  作者：Yanxia Wang、Xinge Zhang、Jing Mu、Chaoxing Li

  DOI：10.1039/c2nj40998d

  日期：——

  Poly(3-methacrylamido phenylboronic acid) (PMAPBA) homopolymer and poly(ethylene glycol)-block-poly(2-acryloxyethyl-galactose) (PEG-b-PAEG) glycopolymer were prepared successfully by reversible addition fragmentation chain transfer (RAFT) polymerization and atom transfer radical polymerization (ATRP), respectively. The formation of boronate crosslinked nanoparticles based on the complexation of PMAPBA and PEG-b-PAEG was confirmed by dynamic light scattering (DLS), thermal analysis, and Alizarin red S (ARS) based colorimetric and fluorescence assays. The nanoparticles showed significant pH, salt, and sugar sensitivity. At pH 5.0 and 6.0, the aggregation and precipitation of the nanoparticles were observed. The particle size increased significantly as pH increased from 7 to 11. The nanoparticles showed obvious sensitivity to glucose, galactose, mannose, and sucrose at pH 10. Due to shielding of the negatively charged phenylboronic acid groups, the aggregation of the boronate crosslinked nanoparticles was found with increase of the salt concentration.

  通过可逆加成片段链转移（RAFT）聚合和原子转移自由基聚合（ATRP）分别成功制备了聚（3-甲基丙烯酰胺基苯基硼酸）均聚物和聚（乙二醇）-嵌段-聚（2-丙烯酰氧基乙基-半乳糖）（PEG-b-PAEG）聚糖。动态光散射（DLS）、热分析和基于茜素红 S（ARS）的比色法和荧光测定证实了基于 PMAPBA 和 PEG-b-PAEG 复合物的硼酸盐交联纳米粒子的形成。纳米颗粒对 pH 值、盐和糖的敏感性很高。在 pH 值为 5.0 和 6.0 时，纳米颗粒出现聚集和沉淀。当 pH 值从 7 升至 11 时，粒径明显增大。在 pH 值为 10 时，纳米粒子对葡萄糖、半乳糖、甘露糖和蔗糖表现出明显的敏感性。由于带负电荷的苯硼酸基团的屏蔽作用，随着盐浓度的增加，硼酸盐交联纳米粒子出现了聚集现象。
• A Water-Soluble Galactose-Decorated Cationic Photodynamic Therapy Agent Based on BODIPY to Selectively Eliminate Biofilm
  作者：Xiaomei Dai、Xuelei Chen、Yu Zhao、Yunjian Yu、Xiaosong Wei、Xinge Zhang、Chaoxing Li

  DOI：10.1021/acs.biomac.7b01316

  日期：2018.1.8

  Here, a water-soluble galactose-functionalized cationic 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-based photodynamic therapy agent was synthesized for selectively eliminating the bacterial biofilm. These conjugates can capture bacteria to form aggregations through electrostatic interaction and then generate a large number of reactive oxygen species (ROS) under visible light irradiation to

  难以根除的细菌生物膜涉及多种严重的慢性感染。在此，合成了水溶性半乳糖官能化的阳离子4,4-二氟-4-硼-3a，4a-二氮杂-s-茚满二烯（BODIPY）基光动力治疗剂，用于选择性消除细菌生物膜。这些结合物可以通过静电相互作用捕获细菌以形成聚集体，然后在可见光照射下产生大量活性氧（ROS），以杀死细菌而不会出现细菌抗性。同时，该试剂可有效抑制和根除革兰氏阳性和革兰氏阴性细菌生物膜。对抗菌机制的深入分析证实，结合物可以快速结合在细菌表面，不可逆转地破坏细菌膜，并明显抑制细胞内酶活性，最终导致细菌死亡。重要的是，这些缀合物对细菌细胞具有比哺乳动物细胞高的选择性，并且对A549细胞没有细胞毒性，也没有明显的溶血活性。总的来说，这种基于水溶性半乳糖修饰的阳离子BODIPY的光动力疗法剂的设计为开发抗药性细菌的疗法提供了有希望的见识。
• Synthetic Route Effect on Macromolecular Architecture: From Block to Gradient Copolymers Based on Acryloyl Galactose Monomer Using RAFT Polymerization
  作者：Pierre Escalé、S. R. Simon Ting、Abdel Khoukh、Laurent Rubatat、Maud Save、Martina H. Stenzel、Laurent Billon

  DOI：10.1021/ma201208u

  日期：2011.8.9

  Statistical, gradient, and block copolymer containing 2-(2',3',4',6'-tetra-O-acetyl-beta-D-galactosyloxy)ethyl acrylate (AcGalEA) glycomonomer and styrene (S) were synthesized by RAFT polymerization using S-methoxycarbonylphenylmethyl dodecyltrithiocarbonate (MCPDT) as control agent. The block copolymer was synthesized by a two-stage experiment, whereas the statistical and gradient copolymers were obtained in one-pot synthesis. Results obtained from the size exclusion chromatography (SEC) and the nuclear magnetic resonance (NMR) reveal that the polymers synthesized by RAFT were controlled. The kinetic of each synthetic route was investigated, and the reactivity ratio of both monomers was estimated by in situ NMR experiments r(AcGalEA) = 0.07 +/- 0.01 and r(S) = 0.7 +/- 0.1. Moreover the AcGalEA moieties were deacetylated to achieve potential amphiphilic bioactive copolymer. The preparation of three different macromolecular architectures to form honeycomb porous films by breath figure process was investigated using atomic force microscopy (AFM).
• “Bottom-Up” Fabrication of BODIPY-Functionalized Fluorescent Hyperbranched Glycopolymers for Hepatoma-Targeted Imaging
  作者：Pei Sun、Hongping Deng、Linzhu Zhou、Yan Wu、Xin Jin、Gangsheng Tong、Xuemei Yu

  DOI：10.1002/mabi.201700381

  日期：2018.5

  A novel type of multivalent and highly specific fluorescent hyperbranched glycopolymers h‐P(GalEA‐co‐VBPT‐co‐BYMA) (hPGVB) is designed and prepared successfully via a facile “bottom‐up” strategy. The acetylated hPGVB is prepared by one‐pot reversible addition‐fragmentation chain transfer (RAFT) copolymerization of acrylate‐type galactose monomers AcGalEA and methacrylate‐type fluorescent monomers BYMA

  通过简便的“自下而上”策略成功设计并制备了新型的多价且高度特异性的荧光超支化糖聚合物h- P（GalEA- co- VBPT- co- BYMA）（h PGVB）。乙酰化的h PGVB是通过丙烯酸酯型半乳糖单体AcGalEA和甲基丙烯酸酯型荧光单体BYMA在惰性型RAFT链转移剂存在下的一锅可逆加成-断裂链转移（RAFT）共聚制备的。脱乙酰化后，将所得的两亲ħPGVB可以在水性介质中自组装成稳定的纳米粒子，显示出强绿色荧光，具有相对较高的量子产率和良好的光稳定性。细胞活力研究表明h PGVB荧光纳米颗粒（FNP）对HepG2和NIH3T3细胞具有出色的生物相容性。更重要的是，与不含半乳糖的荧光超支化聚合物h- P（OEGMA- co- VBPT- co- BYMA）相比，h PEVB FNPs可以被富含去唾液酸糖蛋白（ASGP）受体的HepG2细胞选择性内化，表明其潜在的应用前景生物成像领域。