N,N-dimethyl-N-[2-(9(Z)-octadecanoyloxy)-3-succinyloxy(4-cholesteryloxy)propyl]amine | 926890-46-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: N,N-dimethyl-N-[2-(9(Z)-octadecanoyloxy)-3-succinyloxy(4-cholesteryloxy)propyl]amine
• CAS: 926890-46-2
• 化学式: C₅₄H₉₃NO₆
• 分子量: 852.336
• InChiKey: HFTCALHSNNKKCN-LQRXEFMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.77
• 重原子数：
  61.0
• 可旋转键数：
  29.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-N-[2-(9(Z)-octadecanoyloxy)-3-succinyloxy(4-cholesteryloxy)propyl]amine 、 碘甲烷 以 氯仿 、 二甲基亚砜 为溶剂， 反应 1.0h， 以90%的产率得到N,N,N-trimethyl-N-[2-(9(Z)-octadecanoyloxy)-3-succinyloxy(4-cholesteryloxy)propyl]ammonium iodide
  参考文献：
  名称：

  Design and Assembly of New Nonviral RNAi Delivery Agents by Microwave-Assisted Quaternization (MAQ) of Tertiary Amines

  摘要：

  RNA interference (RNAi) is a gene-silencing phenomenon whereby double-stranded RNA (dsRNA) triggers the sequence-specific degradation of homologous mRNA. RNAi has been quickly and widely applied to discover gene functions and holds great potential to provide a new class of therapeutic agents. However, new chemistry and delivery approaches are greatly needed to silence disease-causing genes without toxic effects. We reasoned that conjugation of the cholesterol moiety to cationic lipids would enhance RNAi efficiencies and lower the toxic effects of lipid-mediated RNAi delivery. Here, we report the first design and synthesis of new cholesterol-conjugated cationic lipids for RNAi delivery using microwave-assisted quaternization (MAQ) of tertiary amines. This strategy can be employed to develop new classes of nonviral gene delivery agents under safe and fast reaction conditions.

  DOI：

  10.1021/bc900482r
• 作为产物：
  描述：

  3-二甲胺基-1,2-丙二醇 在 吡啶 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.08h， 生成 N,N-dimethyl-N-[2-(9(Z)-octadecanoyloxy)-3-succinyloxy(4-cholesteryloxy)propyl]amine
  参考文献：
  名称：

  Design and Assembly of New Nonviral RNAi Delivery Agents by Microwave-Assisted Quaternization (MAQ) of Tertiary Amines

  摘要：

  RNA interference (RNAi) is a gene-silencing phenomenon whereby double-stranded RNA (dsRNA) triggers the sequence-specific degradation of homologous mRNA. RNAi has been quickly and widely applied to discover gene functions and holds great potential to provide a new class of therapeutic agents. However, new chemistry and delivery approaches are greatly needed to silence disease-causing genes without toxic effects. We reasoned that conjugation of the cholesterol moiety to cationic lipids would enhance RNAi efficiencies and lower the toxic effects of lipid-mediated RNAi delivery. Here, we report the first design and synthesis of new cholesterol-conjugated cationic lipids for RNAi delivery using microwave-assisted quaternization (MAQ) of tertiary amines. This strategy can be employed to develop new classes of nonviral gene delivery agents under safe and fast reaction conditions.

  DOI：

  10.1021/bc900482r

文献信息

• WO2007/22030
  申请人：——

  公开号：——

  公开（公告）日：——