Azido-PEG3-SS-PEG3-azide | 1310827-27-0

• 分子结构分类: 有机化合物 - 有机硫化合物
• 英文名称: Azido-PEG3-SS-PEG3-azide
• 英文别名: 1-azido-2-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyldisulfanyl]ethoxy]ethoxy]ethoxy]ethane
• CAS: 1310827-27-0
• 化学式: C₁₆H₃₂N₆O₆S₂
• 分子量: 468.599
• InChiKey: RTXZMZORLYBGQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  30
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  11-叠氮基-3,6,9-三氧杂十一醇 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 55.0h， 生成 Azido-PEG3-SS-PEG3-azide
  参考文献：
  名称：

  Synthesis of a new potential biodegradable disulfide containing poly(ethylene imine)–poly(ethylene glycol) copolymer cross-linked with click cluster for gene delivery

  摘要：

  Poly(ethylene glycol)-grafted-polyethylenimine (PEG-PEI) are promising non-viral gene delivery systems. Herein, we aimed to synthesize a biodegradable disulfide containing PEGylated PEI to attempt to reduce its cytotoxicity and enhance the gene transfer activity. Using click chemistry, low Mw PEI (br. 2 kDa) and short chain length PEG (tetraethylene glycol, TEG) were cross-linked to a high Mw PEG-PEI copolymer (similar to 22 kDa). The chemical structure of the copolymer was characterized using H-1 NMR and GPC The degradation behavior was investigated under in vitro conditions in the presence of 1,4-dithiothreitol (DTT). The gel retardation assay, dynamic light scattering and atomic force microscopy showed good DNA condensation ability by forming polyplexes with small particle size and positive zeta potential. In particular, MTT assay indicated that this PEG-PEI polymer is about 22-fold less toxic than PEI 25k and only 2-fold more toxic than PEI 2k in L929 cell line. After coupling of small PEG chains and cross-linking by disulfide bridges, the transfection efficiency is increased approximately 6-fold in comparison to PEI 2k and still reaches approximately 17% of PEI 25k. Hence, this click cluster cross-linked disulfide containing PEG-PEI copolymer could be an attractive cationic polymer for non-viral gene delivery. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2011.03.038