Ethyl 2-carbonochloridoyloctadecanoate | 41433-76-5

• 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: Ethyl 2-carbonochloridoyloctadecanoate
• 英文别名: ethyl 2-carbonochloridoyloctadecanoate
• CAS: 41433-76-5
• 化学式: C₂₁H₃₉ClO₃
• 分子量: 374.992
• InChiKey: UQTKIUOUOLFZNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  25
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  十六胺 、 Ethyl 2-carbonochloridoyloctadecanoate 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 生成 2-[(hexadecylamino)carbonyl]octandecanoic acid ethyl ester
  参考文献：
  名称：

  Novel Cationic Lipids Based on Malonic Acid Amides Backbone: Transfection Efficacy and Cell Toxicity Properties

  摘要：

  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.

  DOI：

  10.1021/bc9004624
• 作为产物：
  描述：

  2-(ethoxycarbonyl)octadecanoic acid 在 氯化亚砜 作用下， 生成 Ethyl 2-carbonochloridoyloctadecanoate
  参考文献：
  名称：

  Novel Cationic Lipids Based on Malonic Acid Amides Backbone: Transfection Efficacy and Cell Toxicity Properties

  摘要：

  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.

  DOI：

  10.1021/bc9004624

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.