N,N-dimethyl-N-[2-hydroxy-3-succinyloxy(4-cholesteryloxy)propyl]amine | 926890-44-0

• 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-hydroxy-3-succinyloxy(4-cholesteryloxy)propyl]amine
• 英文别名: N,N-dimethyl-N-[2-hydroxy-3-succinyloxy(4-cholesteryloxy)-propyl]amine；1-O-[3-(dimethylamino)-2-hydroxypropyl] 4-O-[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] butanedioate
• CAS: 926890-44-0
• 化学式: C₃₆H₆₁NO₅
• 分子量: 587.884
• InChiKey: WVAWCUDXJLDZSH-PEHMJIIVSA-N

物化性质

• 沸点：
  647.1±55.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-N-[2-hydroxy-3-succinyloxy(4-cholesteryloxy)propyl]amine 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 氯仿 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 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 、 胆固醇琥珀酸单酯 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.08h， 以34%的产率得到N,N-dimethyl-N-[2-hydroxy-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：——
• [EN] ZWITTERIONIC LIPIDS<br/>[FR] LIPIDES ZWITTÉRIONIQUES
  申请人：UNIV CALIFORNIA

  公开号：WO2012024233A3

  公开（公告）日：2012-05-24
• Design and Assembly of New Nonviral RNAi Delivery Agents by Microwave-Assisted Quaternization (MAQ) of Tertiary Amines
  作者：Animesh Ghosh、Koushik Mukherjee、Xinpeng Jiang、Ying Zhou、Joshua McCarroll、James Qu、Pamela M. Swain、Huricha Baigude、Tariq M. Rana

  DOI：10.1021/bc900482r

  日期：2010.9.15

  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.