(9Z)-octadec-9-enyl malonic acid monoethyl ester | 1236057-42-3

• 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: (9Z)-octadec-9-enyl malonic acid monoethyl ester
• 英文别名: (Z)-2-(ethoxycarbonyl)icos-11-enoic acid
• CAS: 1236057-42-3
• 化学式: C₂₃H₄₂O₄
• 分子量: 382.584
• InChiKey: VYKMBSMWLAXKCP-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.68
• 重原子数：
  27.0
• 可旋转键数：
  19.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  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 、 三乙胺 、 三氟乙酸 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 N-[2-(N-(2-aminoethyl)-N-{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：

  1-溴-顺-9-十八碳烯 在 乙醇 、 sodium hydride 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 (9Z)-octadec-9-enyl malonic acid monoethyl ester
  参考文献：
  名称：

  长链β-内酯的合成及其对致病性分枝杆菌的抗菌活性。

  摘要：

  为了寻求新的抗菌剂，开发了一系列新颖的长链和中链单和双取代β-内酯。它们针对三种致病性分枝杆菌-M的活性。通过刃天青素微量滴定分析（REMA）评估脓肿，海藻分枝杆菌和结核分枝杆菌。在合成的16种β-内酯中，只有3-十六烷基氧杂环丁烷-2-酮（VM005）表现出对脓肿分支杆菌的有希望的活性，而大多数β-内酯表现出了有趣的抗海藻分支杆菌的活性，类似于经典抗生素，异烟肼。关于结核分枝杆菌，发现有六种化合物对这种分枝杆菌有活性，与β-内酯VM008 [反式-（Z）-3-（十六烷基-7-烯-1-基）-4-丙基氧杂环丁烷-2-一]是最好的生长抑制剂。

  DOI：

  10.1002/cmdc.201800720

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.