N-[tris(3-(N-tert-butoxycarbonylamino)propyl)methyl]pentadecanamide | 1042940-02-2

• 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-[tris(3-(N-tert-butoxycarbonylamino)propyl)methyl]pentadecanamide
• CAS: 1042940-02-2
• 化学式: C₄₀H₇₈N₄O₇
• 分子量: 727.082
• InChiKey: ATHIXDFGCMUBHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.85
• 重原子数：
  51.0
• 可旋转键数：
  26.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  144.09
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-[tris(3-(N-tert-butoxycarbonylamino)propyl)methyl]pentadecanamide 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以100%的产率得到N-[tris(3-(amino)propyl)methyl]pentadecanamide trihydrochloride
  参考文献：
  名称：

  Tripod-like Cationic Lipids as Novel Gene Carriers

  摘要：

  An innovative family of tridentate-cationic "single-chained lipids" designed to enhance DNA compaction and to promote endosomal escape was synthesized by coupling various lipids to a multibranched scaffold. DNA retardation assays confirmed the ability of the most members of the library to complex DNA. Classical molecular dynamics simulations performed on the lauryl derivative, bound to a short strand of DNA in aqueous solution supported these observations. These showed that two "arms" of the tripodal molecule are ideally suited to forming strong Coulombic interactions with two contiguous phosphate groups from the DNA backbone while the lipophilic tail stays perpendicular to the DNA helix. Gene transfer abilities of the library were assessed in multiple cell lines (CHO, Cos7, and 16HBE14o-) with some library members giving excellent transfection abilities and low cytotoxicity, supporting the use of this tripodal approach for the development of efficient gene delivery agents.

  DOI：

  10.1021/jm701493f
• 作为产物：
  描述：

  十五烷酸 、 di-tert-butyl (4-amino-4-(3-((tert-butoxycarbonyl)amino)propyl)heptane-1,7-diyl)dicarbamate 在 N,N'-二环己基碳二亚胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以88%的产率得到N-[tris(3-(N-tert-butoxycarbonylamino)propyl)methyl]pentadecanamide
  参考文献：
  名称：

  Tripod-like Cationic Lipids as Novel Gene Carriers

  摘要：

  An innovative family of tridentate-cationic "single-chained lipids" designed to enhance DNA compaction and to promote endosomal escape was synthesized by coupling various lipids to a multibranched scaffold. DNA retardation assays confirmed the ability of the most members of the library to complex DNA. Classical molecular dynamics simulations performed on the lauryl derivative, bound to a short strand of DNA in aqueous solution supported these observations. These showed that two "arms" of the tripodal molecule are ideally suited to forming strong Coulombic interactions with two contiguous phosphate groups from the DNA backbone while the lipophilic tail stays perpendicular to the DNA helix. Gene transfer abilities of the library were assessed in multiple cell lines (CHO, Cos7, and 16HBE14o-) with some library members giving excellent transfection abilities and low cytotoxicity, supporting the use of this tripodal approach for the development of efficient gene delivery agents.

  DOI：

  10.1021/jm701493f