6-iodo-6-deoxy-2,3,4,5,2',3',4',5',6'-O-acetyl-α,α-D-trehalose | 25227-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-iodo-6-deoxy-2,3,4,5,2',3',4',5',6'-O-acetyl-α,α-D-trehalose
• 英文别名: 6-Desoxy-6-iod-hepta-O-acetyl-α,α-trehalose；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-(iodomethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 25227-12-7
• 化学式: C₂₆H₃₅IO₁₇
• 分子量: 746.458
• InChiKey: GDGJJQBHGXJTEY-PCIRLDFKSA-N

物化性质

• 沸点：
  663.1±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.04
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  211.79
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  6-iodo-6-deoxy-2,3,4,5,2',3',4',5',6'-O-acetyl-α,α-D-trehalose 生成 Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  JEZO, I.;ZEMEK, J., CHEM. PAP., 42,(1988) N 2, C. 271-278

  摘要：

  DOI：
• 作为产物：
  描述：

  海藻糖 、 乙酸酐 在 碘 、 三苯基膦 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 为溶剂， 反应 5.0h， 以22.3 g的产率得到6-iodo-6-deoxy-2,3,4,5,2',3',4',5',6'-O-acetyl-α,α-D-trehalose
  参考文献：
  名称：

  Poly(trehalose): Sugar-Coated Nanocomplexes Promote Stabilization and Effective Polyplex-Mediated siRNA Delivery

  摘要：

  When nanoparticles interact with their environment, the nature of that interaction is governed largely by the properties of its outermost surface layer. Here, we exploit the exceptional properties of a common disaccharide, trehalose, which is well-known for its unique biological stabilization effects. To this end, we have developed a synthetic procedure that readily affords a polymer of this disaccharide, poly-(methacrylamidotrehalose) or "poly(trehalose)" and diblock copolycations containing this polymer with 51 repeat units chain extended with aminoethylmethacrylamide (AEMA) at three degrees of polymerization (n = 34, 65, and 84). Two series of experiments were conducted to study these diblock copolymers in detail and to compare their properties to two control polymers [PEG-P(AEMA) and P(AEMA)]. First, we demonstrate that the poly(trehalose) coating ensures colloidal stability of polyplexes containing siRNA in the presence of high salt concentrations and serum proteins. Poly(trehalose) retains the ability of trehalose to lower the phase transition energy associated with water freezing and can protect siRNA polyplexes during freeze-drying, allowing complete nanoparticle resuspension without loss of biological function. Second, we show that siRNA polyplexes coated with poly(trehalose) have exceptional cellular internalization into glioblastoma cells that proceeds with zero-order kinetics. Moreover, the amount of siRNA delivered by poly(trehalose) block copolycations can be controlled by the siRNA concentration in cell culture media. Using confocal microscopy we show that trehalose-coated polyplexes undergo active trafficking in cytoplasm upon internalization and significant siRNA-induced target gene down-regulation was achieved with an IC50 of 19 nM. These findings coupled with a negligible cytotoxicity suggests that poly(trehalose) has the potential to serve as an important component of therapeutic nanoparticle formulations of nucleic acids and has great promise to be extended as a new coating for other nanobased technologies and macromolecules, in particular, those related to nanomedicine applications.

  DOI：

  10.1021/ja404941p