3-dimethylamine propyl-1,2-ditetradecylcarbamate | 1016626-64-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-dimethylamine propyl-1,2-ditetradecylcarbamate
• 英文别名: [3-(dimethylamino)-2-(tetradecylcarbamoyloxy)propyl] N-tetradecylcarbamate
• CAS: 1016626-64-4
• 化学式: C₃₅H₇₁N₃O₄
• 分子量: 597.966
• InChiKey: VUGGPNZHNHGUBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  42
• 可旋转键数：
  33
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-dimethylamine propyl-1,2-ditetradecylcarbamate 、 氯甲烷 以97%的产率得到N,N,N-trimethyl-2,3-bis((tetradecylcarbamoyl)oxy)propan-1-aminium chloride
  参考文献：
  名称：

  氨基甲酸酯连接的阳离子脂质，用于基因传递。

  摘要：

  合成了一系列阳离子脂质1a-p，它们具有可变长度的烃链，交替的季铵头，烃链和季铵头之间的氨基甲酸酯键以及与它们组合的不同阴离子，用于脂质体介导的基因传递。由上述阳离子脂质形成的阳离子脂质体将两个质粒DNA pGL3-control和pGFP-N2转移到五个哺乳动物细胞系中，某些阳离子脂质体的转染效率优于或平行于两种商业转染剂，Lipofectamine2000和Sofast。

  DOI：

  10.1016/j.bmc.2007.10.009
• 作为产物：
  描述：

  十四胺 在 三乙胺 作用下， 以 甲苯 为溶剂， 生成 3-dimethylamine propyl-1,2-ditetradecylcarbamate
  参考文献：
  名称：

  Synthesis and evaluation of mono- and multi-hydroxyl low toxicity pH-sensitive cationic lipids for drug delivery

  摘要：

  Cationic lipids can easily assemble into spherical liposomes in aqueous phase which showed unique superiority in drug and gene delivery. However, the toxicity of cationic lipids is still an obstacle to application. To develop low toxicity cationic lipids, we designed two cationic lipids contained different number of hydroxyl groups. Biocompatible mono-hydroxyl and multi-hydroxyl galactose head group was respectively modified to a biodegradable quaternary amine lipid, and two novel hydroxyl cationic lipids were synthesized and characterized by MS, H-1 NMR and C-13 NMR. Two lipids showed good surface activity and both of them can assemble to about 80 nm stable small unilamellar vesicles (SUVs) with cholesterol in aqueous phase. Both of lipids showed relatively lower toxicity than the well-known cationic lipid 1,2-dioleoyl-3-trimethylammonium-propane (DOTAP). In vitro 24 h IC50, of two assemblies were more than 50 mu g/mL, which were about 10 mu g/mL higher than the IC50, of DOTAP. Multi-hydroxyl galactose lipids group showed much lower toxicity than mono-hydroxyl lipids group. Moreover, Both of the assemblies with lower hemolysis were nearly non-hemolytic risk under the concentration of 30 mu g/mL. Transmission electron microscopy (TEM) and dynamic light scattering (DLS) showed that the average sizes of both doxorubicin (DOX) loaded liposomes were about 110 nm. The DOX entrapment efficiencies of galactose liposome and mono-hydroxyl liposome were 58% and 91%, respectively. Both of the DOX loaded liposomes were stable after one month placed at room temperature. Two DOX loaded liposomes showed better anti-cancer effect than free DOX above 5 mu g/mL, and they can be internalized into cells and produce more release of DOX inside MCF-7 cells and HepG2 cells at pH 5.0. These results suggested that synthesized lipids are suitable as potential low toxicity cationic drug delivery systems.

  DOI：

  10.1016/j.ejps.2019.03.018

文献信息

• Synthesis and Characterization of Novel Cationic Lipids Derived from Thio Galactose
  作者：Weihong Qiao、Min Zhou、Limei Luo

  DOI：10.1007/s11743-013-1474-0

  日期：2014.3

  Two double chain cationic lipids QAS Cn‐2‐S (n = 12, 14) derived from thio galactose and carbamate‐linkage tertiary amine were synthesized and their structures were confirmed by MS, TOF‐MS, 1H NMR and 13C NMR. The QAS C12‐2‐S revealed superior surface activity compared with QAS C14‐2‐S with lower CMC and γCMC. Though Lipo C12‐2‐S displayed large average particle‐size with high polydispersity, positive

  合成了两个由硫代半乳糖和氨基甲酸酯键联的叔胺衍生的双链阳离子脂质QAS C n -2-S（n = 12，14），并通过MS，TOF-MS，1 H NMR和13 C NMR证实了其结构。的QASÇ 12与QAS则为C -2-S显示优异的表面活性14 -2-S具有较低CMC和γ CMC。虽然前列Ç 12 -2-S显示大的平均粒径的高多分散性，带正电荷的脂微球Ç Ñ -2-S可与带负电的DNA进行组合，也负染TEM图像证实囊泡的形成。以上所有证明Lipo C n‐2‐S有助于基因转染。
• Synthesis and Characterization of Carbamate‐Linked Cationic Lipids with Hydroxyethyl Group
  作者：Weihong Qiao、Zhibo Zheng、Wenhui Qu、Shumin Zhang

  DOI：10.1007/s11746-012-2115-x

  日期：2012.12

  AbstractA series of cationic lipids with a carbamate linkage and a hydroxyethyl head group were designed and synthesized for gene delivery. All of the products were characterized by 1H NMR and MS. Cationic liposomes were prepared using the cationic lipid and the liposome states were studied by TEM and Nano Particle Size and Potential Analyzer. Liposomes were approximately spherical structures, the mean diameter was about 150 nm, the zeta‐potential was about 40 mV.