1,2-bis(octadec-4-ynoyloxy)-3-(dimethylamino)propane | 873917-96-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,2-bis(octadec-4-ynoyloxy)-3-(dimethylamino)propane
• 英文别名: [3-(Dimethylamino)-2-octadec-4-ynoyloxypropyl] octadec-4-ynoate
• CAS: 873917-96-5
• 化学式: C₄₁H₇₃NO₄
• 分子量: 644.035
• InChiKey: NYTJVJJGPYKXRN-UHFFFAOYSA-N

物化性质

• 沸点：
  682.7±55.0 °C(Predicted)
• 密度：
  0.938±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.9
• 重原子数：
  46
• 可旋转键数：
  33
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-bis(octadec-4-ynoyloxy)-3-(dimethylamino)propane 、 硫酸二甲酯 以 丙酮 为溶剂， 反应 24.0h， 以75%的产率得到2,3-Di(octadec-4-ynoyloxy)propyl-trimethylazanium;methyl sulfate
  参考文献：
  名称：

  In Vivo Studies of Dialkynoyl Analogues of DOTAP Demonstrate Improved Gene Transfer Efficiency of Cationic Liposomes in Mouse Lung

  摘要：

  A novel set of dialkynoyl analogues of the cationic, gene delivery lipid DOTAP (1) was synthesized. Structure-activity studies demonstrate that replacement of the cis-double bonds of DOTAP with triple bonds in varying positions alters both the physical properties of the resultant cationic liposome-DNA complexes and their biological functionalities, both in vitro and in vivo. Particularly, in vivo studies demonstrate that pDNA transfection of mouse lung endothelial cells with lead analogue DS(14-yne)TAP (4):cholesterol lipoplexes exhibits double the transfection level with less associated toxicity relative to the well-established DOTAP:cholesterol system. In fact, 4:cholesterol delivers up to 3 times the dose of pDNA in mice than can be tolerated by DOTAP, leading to nearly 3 times greater marker-gene expression. X-ray diffraction studies suggest that lipoplexes containing analogue 4 display increased stability at physiological temperatures. Our results thus suggest that analogue 4 is a potentially strong candidate for the gene therapy of lung tumors.

  DOI：

  10.1021/jm0507227
• 作为产物：
  描述：

  2-(4-戊炔氧基)四氢-2H-吡喃 在 甲醇 、 正丁基锂 、 Jones's reagent 、 对甲苯磺酸 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 、 丙酮 为溶剂， 反应 42.0h， 生成 1,2-bis(octadec-4-ynoyloxy)-3-(dimethylamino)propane
  参考文献：
  名称：

  In Vivo Studies of Dialkynoyl Analogues of DOTAP Demonstrate Improved Gene Transfer Efficiency of Cationic Liposomes in Mouse Lung

  摘要：

  A novel set of dialkynoyl analogues of the cationic, gene delivery lipid DOTAP (1) was synthesized. Structure-activity studies demonstrate that replacement of the cis-double bonds of DOTAP with triple bonds in varying positions alters both the physical properties of the resultant cationic liposome-DNA complexes and their biological functionalities, both in vitro and in vivo. Particularly, in vivo studies demonstrate that pDNA transfection of mouse lung endothelial cells with lead analogue DS(14-yne)TAP (4):cholesterol lipoplexes exhibits double the transfection level with less associated toxicity relative to the well-established DOTAP:cholesterol system. In fact, 4:cholesterol delivers up to 3 times the dose of pDNA in mice than can be tolerated by DOTAP, leading to nearly 3 times greater marker-gene expression. X-ray diffraction studies suggest that lipoplexes containing analogue 4 display increased stability at physiological temperatures. Our results thus suggest that analogue 4 is a potentially strong candidate for the gene therapy of lung tumors.

  DOI：

  10.1021/jm0507227