1,3-dioleoyl-2-(4-iodobutanoyl)glycerol | 195257-58-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,3-dioleoyl-2-(4-iodobutanoyl)glycerol
• 英文别名: [2-(4-iodobutanoyloxy)-3-[(Z)-octadec-9-enoyl]oxypropyl] (Z)-octadec-9-enoate
• CAS: 195257-58-0
• 化学式: C₄₃H₇₇IO₆
• 分子量: 816.985
• InChiKey: FGRYLPUIQJIZAV-CLFAGFIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.5
• 重原子数：
  50
• 可旋转键数：
  41
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-dioleoyl-2-(4-iodobutanoyl)glycerol 、 三甲胺 以 乙醚 为溶剂， 反应 12.0h， 以78%的产率得到YKS-220
  参考文献：
  名称：

  Symmetrical cationic triglycerides

  摘要：

  Some cationic triglycerides 1Aa-1Cb which have a symmetrical structure were effectively synthesized and formulated into cationic liposomes with the co-lipid dioleoylphosphatidylethanolamine (DOPE) and/or dilauroylphosphatidylcholine (DLPC). The plasmid encoding a luciferase was delivered into CHO cells by using these cationic liposomes. Our symmetrical cationic triglycerides showed high transfection activity when DOPE was used as a co-lipid. Among the symmetrical cationic triglycerides synthesized here, 1Ab and 1Ac, which have an oleoyl group at the 1- and 3-position in the glycerol backbone and also have a relatively long linker connecting the 2-hydroxy group in glycerol with the quaternary ammonium head group, were found to be the most suitable for gene delivery into cells. The transfection activity of the symmetrical cationic triglyceride 1Ab was comparable with that of its asymmetrical congener 6 and several times higher than that of Lipofectin(R). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00242-x
• 作为产物：
  描述：

  1,3-dioleoyl-2-(4-chlorobutanoyl)glycerol 在 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 48.0h， 以88%的产率得到1,3-dioleoyl-2-(4-iodobutanoyl)glycerol
  参考文献：
  名称：

  Symmetrical cationic triglycerides

  摘要：

  Some cationic triglycerides 1Aa-1Cb which have a symmetrical structure were effectively synthesized and formulated into cationic liposomes with the co-lipid dioleoylphosphatidylethanolamine (DOPE) and/or dilauroylphosphatidylcholine (DLPC). The plasmid encoding a luciferase was delivered into CHO cells by using these cationic liposomes. Our symmetrical cationic triglycerides showed high transfection activity when DOPE was used as a co-lipid. Among the symmetrical cationic triglycerides synthesized here, 1Ab and 1Ac, which have an oleoyl group at the 1- and 3-position in the glycerol backbone and also have a relatively long linker connecting the 2-hydroxy group in glycerol with the quaternary ammonium head group, were found to be the most suitable for gene delivery into cells. The transfection activity of the symmetrical cationic triglyceride 1Ab was comparable with that of its asymmetrical congener 6 and several times higher than that of Lipofectin(R). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00242-x

文献信息

• A symmetrical and biodegradable cationic lipid. Synthesis and application for efficient gene transfection
  作者：Satoshi Obika、Wei Yu、Atsuko Shimoyama、Takeshi Uneda、Kazuyuki Miyashita、Takefumi Doi、Takeshi Imanishi

  DOI：10.1016/s0960-894x(97)00317-x

  日期：1997.7

  A novel cationic lipid with a symmetrical and biodegradable structure was synthesized, and the transfection efficiency and the cytotoxicity of the cationic liposomes composed of the cationic lipid and dioleoylphosphatidylethanolamine (DOPE) were studied. (C) 1997 Elsevier Science Ltd.