2-deoxy-2-methacrylamido-1,3,4,6-tetra(O-trimethylsilyl)-α-D-glucopyranose | 151666-30-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-deoxy-2-methacrylamido-1,3,4,6-tetra(O-trimethylsilyl)-α-D-glucopyranose
• 英文别名: 2-methyl-N-[(2R,3R,4R,5R,6R)-2,4,5-tris(trimethylsilyloxy)-6-(trimethylsilyloxymethyl)oxan-3-yl]prop-2-enamide
• CAS: 151666-30-7
• 化学式: C₂₂H₄₉NO₆Si₄
• 分子量: 535.976
• InChiKey: JPPZBJMPEUZLSO-CDVBAKLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-amino-2-deoxy-1,3,4,6-tetra-O-(trimethylsilyl)-α-D-glucopyranose 、 甲基丙烯酰氯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-deoxy-2-methacrylamido-1,3,4,6-tetra(O-trimethylsilyl)-α-D-glucopyranose
  参考文献：
  名称：

  Glucose-Functionalized, Serum-Stable Polymeric Micelles from the Combination of Anionic and RAFT Polymerizations

  摘要：

  Poly(ethylene-alt-propylene)-poly[(N,N-dimethylacrylamide)-grad-(2-methacrylamido glucopyranose)] (PEP-poly(DMA-grad-MAG), or PG) diblock terpolymers were synthesized by combining anionic and reversible addition-fragmentation chain transfer (RAFT) polymerizations. An omega-trithiocarbonate-functionalized PEP homopolymer served as the macromolecular chain transfer agent (macroCTA), and RAFT copolymerizations of DMA and a trimethylsilyl-protected MAG (TMS-MAG) monomer gave a family of PG diblock terpolymers after hydrolysis. The terpolymers had similar degrees of polymerization, and the MAG content ranged from 3.5 to 39 mol % in the hydrophilic block. At 70 degrees C, the reactivity ratios of DMA (1) and TMS-MAG (2) were determined to be r(1) = 1.86 +/- 0.07 and r(2) = 0.16 +/- 0.01, and thus the poly(meth)acrylamide blocks in the PG diblock terpolymers were likely to be gradient copolymers. Micellar dispersions from PG diblock polymers in water were examined by cryogenic transmission electron microscopy (cryo-TEM) and dynamic light scattering (DLS). Spherical micelles with core radii of ca. 7 nm and overall hydrodynamic radii of ca. 15 nm were the predominant morphologies observed in all samples prepared by sequential nanoprecipitation and dialysis. The electron-dense MAG moieties greatly increased the native contrast of the micellar coronae, which were clearly viewed as gray halos around the micellar cores in samples with relatively large MAG content. The stability of the glucose-installed micelles was tested in four biologically relevant media, from simple phosphate-buffered saline (PBS) to fetal bovine serum (FBS), using a combination of DLS and cryo-TEM measurements. Micellar dispersions from a PG diblock terpolymer with 16 mol % of MAG of the hydrophilic block were stable in 100% FBS over at least 14 h, suggesting their minimal interactions with serum proteins. Control experiments suggested that micelles composed of PDMA alone in the corona had similar serum stabilities. These sugar-functionalized micelles hold promise as in vivo drug delivery vehicles to possibly prolong circulation time after intravenous administration.

  DOI：

  10.1021/ma300218n

文献信息

• Glucose-Functionalized, Serum-Stable Polymeric Micelles from the Combination of Anionic and RAFT Polymerizations
  作者：Ligeng Yin、Molly C. Dalsin、Antons Sizovs、Theresa M. Reineke、Marc A. Hillmyer

  DOI：10.1021/ma300218n

  日期：2012.5.22

  Poly(ethylene-alt-propylene)-poly[(N,N-dimethylacrylamide)-grad-(2-methacrylamido glucopyranose)] (PEP-poly(DMA-grad-MAG), or PG) diblock terpolymers were synthesized by combining anionic and reversible addition-fragmentation chain transfer (RAFT) polymerizations. An omega-trithiocarbonate-functionalized PEP homopolymer served as the macromolecular chain transfer agent (macroCTA), and RAFT copolymerizations of DMA and a trimethylsilyl-protected MAG (TMS-MAG) monomer gave a family of PG diblock terpolymers after hydrolysis. The terpolymers had similar degrees of polymerization, and the MAG content ranged from 3.5 to 39 mol % in the hydrophilic block. At 70 degrees C, the reactivity ratios of DMA (1) and TMS-MAG (2) were determined to be r(1) = 1.86 +/- 0.07 and r(2) = 0.16 +/- 0.01, and thus the poly(meth)acrylamide blocks in the PG diblock terpolymers were likely to be gradient copolymers. Micellar dispersions from PG diblock polymers in water were examined by cryogenic transmission electron microscopy (cryo-TEM) and dynamic light scattering (DLS). Spherical micelles with core radii of ca. 7 nm and overall hydrodynamic radii of ca. 15 nm were the predominant morphologies observed in all samples prepared by sequential nanoprecipitation and dialysis. The electron-dense MAG moieties greatly increased the native contrast of the micellar coronae, which were clearly viewed as gray halos around the micellar cores in samples with relatively large MAG content. The stability of the glucose-installed micelles was tested in four biologically relevant media, from simple phosphate-buffered saline (PBS) to fetal bovine serum (FBS), using a combination of DLS and cryo-TEM measurements. Micellar dispersions from a PG diblock terpolymer with 16 mol % of MAG of the hydrophilic block were stable in 100% FBS over at least 14 h, suggesting their minimal interactions with serum proteins. Control experiments suggested that micelles composed of PDMA alone in the corona had similar serum stabilities. These sugar-functionalized micelles hold promise as in vivo drug delivery vehicles to possibly prolong circulation time after intravenous administration.