N-[3-羟基-2-(十四烷酰氨基)丙基]十四烷酰胺 | 108861-06-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: N-[3-羟基-2-(十四烷酰氨基)丙基]十四烷酰胺
• 英文名称: N,N'-dimyristoyl-1,2-diaminopropan-3-ol
• 英文别名: N,N'-(3-Hydroxypropane-1,2-diyl)ditetradecanamide；N-[3-hydroxy-2-(tetradecanoylamino)propyl]tetradecanamide
• CAS: 108861-06-9
• 化学式: C₃₁H₆₂N₂O₃
• 分子量: 510.845
• InChiKey: PFCSGHBSJUYUOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  36
• 可旋转键数：
  28
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[3-羟基-2-(十四烷酰氨基)丙基]十四烷酰胺 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 N,N-dimyristoyl-1,2-diaminopropyl-3-carbamoyl-(N,N-dimethylaminoethane)
  参考文献：
  名称：

  Synthesis, in vitro transfection activity and physicochemical characterization of novel N,N′-diacyl-1,2-diaminopropyl-3-carbamoyl-(dimethylaminoethane) amphiphilic derivatives

  摘要：

  A novel series of NN'-diacyl-1,2-diaminopropyl-3-carbamoyl-(dimethylaminoethane) cationic derivatives was synthesized and screened for in vitro transfection activity at different charge ratios in the presence and absence of the helper lipids DOPE and cholesterol. Physicochemical properties of lipid-DNA complexes were studied by gel electrophoresis, fluorescence spectroscopy and dynamic light scattering. The interfacial properties of the lipids in isolation were studied using the Langmuir film balance technique at 23 degreesC. It was found that only lipoplexes formulated with the dioleoyl derivative, 1,21mt[5], mediated significant in vitro transfection activity. Optimum activity was obtained with 1,21mt[5]/DOPE mixture at a +/-charge ratio of 2. In agreement with the transfection results, 1,21mt[5] was the only lipid found to complex and retard DNA migration as verified by gel electrophoresis. Despite the efficient complexation, no significant condensation of plasmid DNA was observed as indicated by fluorescence spectroscopy measurements. Monolayer studies showed that the dioleoyl derivative 1,21mt[5] was the only lipid that existed in an all liquid-expanded state with a collapse area and collapse pressure of 59.5 Angstrom(2) and 38.7 mN/m, respectively. This lipid was also found to have the highest elasticity with a compressibility modulus at monolayer collapse of 80.4 mN/m. In conclusion, increased acyl chain fluidity and high molecular elasticity of cationic lipids were found to correlate with improved transfection activity. (C) 2004 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2004.09.017
• 作为产物：
  描述：

  methyl (N,N'-dimyristoyl)-2,3-diaminopropionate 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 以88.3%的产率得到N-[3-羟基-2-(十四烷酰氨基)丙基]十四烷酰胺
  参考文献：
  名称：

  Synthesis, in vitro transfection activity and physicochemical characterization of novel N,N′-diacyl-1,2-diaminopropyl-3-carbamoyl-(dimethylaminoethane) amphiphilic derivatives

  摘要：

  A novel series of NN'-diacyl-1,2-diaminopropyl-3-carbamoyl-(dimethylaminoethane) cationic derivatives was synthesized and screened for in vitro transfection activity at different charge ratios in the presence and absence of the helper lipids DOPE and cholesterol. Physicochemical properties of lipid-DNA complexes were studied by gel electrophoresis, fluorescence spectroscopy and dynamic light scattering. The interfacial properties of the lipids in isolation were studied using the Langmuir film balance technique at 23 degreesC. It was found that only lipoplexes formulated with the dioleoyl derivative, 1,21mt[5], mediated significant in vitro transfection activity. Optimum activity was obtained with 1,21mt[5]/DOPE mixture at a +/-charge ratio of 2. In agreement with the transfection results, 1,21mt[5] was the only lipid found to complex and retard DNA migration as verified by gel electrophoresis. Despite the efficient complexation, no significant condensation of plasmid DNA was observed as indicated by fluorescence spectroscopy measurements. Monolayer studies showed that the dioleoyl derivative 1,21mt[5] was the only lipid that existed in an all liquid-expanded state with a collapse area and collapse pressure of 59.5 Angstrom(2) and 38.7 mN/m, respectively. This lipid was also found to have the highest elasticity with a compressibility modulus at monolayer collapse of 80.4 mN/m. In conclusion, increased acyl chain fluidity and high molecular elasticity of cationic lipids were found to correlate with improved transfection activity. (C) 2004 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2004.09.017

文献信息

• Synthesis, in vitro transfection activity and physicochemical characterization of novel N,N′-diacyl-1,2-diaminopropyl-3-carbamoyl-(dimethylaminoethane) amphiphilic derivatives
  作者：Ahmad Aljaberi、Pensung Chen、Michalakis Savva

  DOI：10.1016/j.chemphyslip.2004.09.017

  日期：2005.2

  A novel series of NN'-diacyl-1,2-diaminopropyl-3-carbamoyl-(dimethylaminoethane) cationic derivatives was synthesized and screened for in vitro transfection activity at different charge ratios in the presence and absence of the helper lipids DOPE and cholesterol. Physicochemical properties of lipid-DNA complexes were studied by gel electrophoresis, fluorescence spectroscopy and dynamic light scattering. The interfacial properties of the lipids in isolation were studied using the Langmuir film balance technique at 23 degreesC. It was found that only lipoplexes formulated with the dioleoyl derivative, 1,21mt[5], mediated significant in vitro transfection activity. Optimum activity was obtained with 1,21mt[5]/DOPE mixture at a +/-charge ratio of 2. In agreement with the transfection results, 1,21mt[5] was the only lipid found to complex and retard DNA migration as verified by gel electrophoresis. Despite the efficient complexation, no significant condensation of plasmid DNA was observed as indicated by fluorescence spectroscopy measurements. Monolayer studies showed that the dioleoyl derivative 1,21mt[5] was the only lipid that existed in an all liquid-expanded state with a collapse area and collapse pressure of 59.5 Angstrom(2) and 38.7 mN/m, respectively. This lipid was also found to have the highest elasticity with a compressibility modulus at monolayer collapse of 80.4 mN/m. In conclusion, increased acyl chain fluidity and high molecular elasticity of cationic lipids were found to correlate with improved transfection activity. (C) 2004 Elsevier Ireland Ltd. All rights reserved.