N-{2-[N,N-bis(2-aminoethyl)amino]ethyl}-N',2-di[(9Z)-octadec-9-enyl]propane diamide | 1221575-24-1

• 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: N-{2-[N,N-bis(2-aminoethyl)amino]ethyl}-N',2-di[(9Z)-octadec-9-enyl]propane diamide
• 英文别名: N-[bis(2-aminoethyl)amino]ethyl-N',2-di[(9Z)-octadec-9-enyl]propane diamide；N-{2-[N,N-bis(2-aminoethyl)amino]ethyl}-N',2-[(9Z)-octadec-9-enyl]propane diamide
• CAS: 1221575-24-1
• 化学式: C₄₅H₈₉N₅O₂
• 分子量: 732.234
• InChiKey: RZDJAPCMBFZTTB-CLFAGFIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.52
• 重原子数：
  52.0
• 可旋转键数：
  41.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  113.48
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-{2-[N,N-bis(2-aminoethyl)amino]ethyl}-N',2-di[(9Z)-octadec-9-enyl]propane diamide 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 N-[2-(N,N-bis{2-[N-(2,6-diamino-1-oxohexyl)amino]ethyl}amino)ethyl]-N',2-di[(9Z)-octadec-9-enyl]propane diamide
  参考文献：
  名称：

  Synthesis and DNA transfection properties of new head group modified malonic acid diamides

  摘要：

  Malonic acid diamides with two long hydrophobic alkyl chains and a basic polar head group as a new class of non-viral gene transferring compounds have shown high transfection efficiency and moderate toxicity. Based on the results obtained with saturated and unsaturated alkyl residues new derivatives with a more complex head group structure have been synthesized. For this purpose, cationic respectively basic groups were introduced by one or two lysine residues bound via tris(aminoethyl)amine spacer to the malonic acid diamide backbone. By studying in vitro gene delivery an increase of transfection efficacy was observed when using lipids with at least one unsaturated alkyl chain. This leads to cationic lipids exhibiting comparable or even higher transfection efficacies compared to the commercially available transfection agents LipofectAmine (TM) and SuperFect (TM). Phase transitions and phase structures of selected compounds have been analyzed and discussed in terms of transfection abilities. Particle size and zeta potential of liposomes and lipoplexes were also determined. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2011.02.022
• 作为产物：
  描述：

  (9Z)-octadec-9-enyl malonic acid monoethyl ester 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-{2-[N,N-bis(2-aminoethyl)amino]ethyl}-N',2-di[(9Z)-octadec-9-enyl]propane diamide
  参考文献：
  名称：

  Synthesis and DNA transfection properties of new head group modified malonic acid diamides

  摘要：

  Malonic acid diamides with two long hydrophobic alkyl chains and a basic polar head group as a new class of non-viral gene transferring compounds have shown high transfection efficiency and moderate toxicity. Based on the results obtained with saturated and unsaturated alkyl residues new derivatives with a more complex head group structure have been synthesized. For this purpose, cationic respectively basic groups were introduced by one or two lysine residues bound via tris(aminoethyl)amine spacer to the malonic acid diamide backbone. By studying in vitro gene delivery an increase of transfection efficacy was observed when using lipids with at least one unsaturated alkyl chain. This leads to cationic lipids exhibiting comparable or even higher transfection efficacies compared to the commercially available transfection agents LipofectAmine (TM) and SuperFect (TM). Phase transitions and phase structures of selected compounds have been analyzed and discussed in terms of transfection abilities. Particle size and zeta potential of liposomes and lipoplexes were also determined. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2011.02.022

文献信息

• Novel Cationic Lipids Based on Malonic Acid Amides Backbone: Transfection Efficacy and Cell Toxicity Properties
  作者：Martin Heinze、Gerald Brezesinski、Bodo Dobner、Andreas Langner

  DOI：10.1021/bc9004624

  日期：2010.4.21

  Gene delivery using nonviral approaches has been extensively studied as a basic tool for intracellular gene transfer. Despite intensive research activity, the aim of creating a vector which meets all necessary demands has still not been reached. One possibility to solve the nonviral vector associated problem of low transfection efficacy is the development of new cationic amphiphiles. Therefore, the non-glycerol-based cationic lipids 1-9 have been synthesized and tested for in vitro gene delivery experiments. The backbone structure of the lipids consists of a malonic acid diamide with two long hydrophobic chains. The degree of saturation of the hydrophobic chains and the structure of the polar cationic headgroup were varied. The preparation follows an easy process and facilitates the trouble-free insertion of different alkyl chains. By studying in vitro gene delivery an increase of transfection efficacy was observed when using at least one unsaturated alkyl chain in the hydrophobic part and lysine or bis(2-aminoethyl)aminoethylamid as hydrophilic headgroup. This leads to cationic lipids exhibiting comparable or even higher transfection efficacies compared to the commercially available LipolectAmine and Super Feet.