(R)-1,2-bis-tetradecyloxy-3-dimethylamine propane | 680220-02-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-1,2-bis-tetradecyloxy-3-dimethylamine propane
• 英文别名: (S)-1,2-Bis-tetradecyloxy-3-dimethylamino propane；(2S)-N,N-dimethyl-2,3-di(tetradecoxy)propan-1-amine
• CAS: 680220-02-4
• 化学式: C₃₃H₆₉NO₂
• 分子量: 511.916
• InChiKey: ZVJAPVDDCYWINZ-XIFFEERXSA-N

物化性质

• 沸点：
  565.1±35.0 °C(Predicted)
• 密度：
  0.862±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  36
• 可旋转键数：
  31
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-bis-(2-bromoethoxy)propane-2-ol 、 (R)-1,2-bis-tetradecyloxy-3-dimethylamine propane 以 乙醇 为溶剂， 反应 120.0h， 以78%的产率得到
  参考文献：
  名称：

  Synthesis of novel cationic cardiolipin analogues for the optimal delivery of therapeutic agents

  摘要：

  A novel approach was developed to synthesize cardiolipin analogues containing two quaternary ammonium groups With tetraalkyl chain retaining 'glycerol' moiety, the central core of the molecule. The analogues were synthesized with or without spacer and/or lipid chain length with saturation to tailor lipid-based formulations of therapeutic agents for optimal delivery to target sites. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.044
• 作为产物：
  描述：

  溴代十四烷 在 palladium on activated charcoal 甲醇 、 四溴化碳 、 氢气 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、344.75 kPa 条件下， 反应 84.0h， 生成 (R)-1,2-bis-tetradecyloxy-3-dimethylamine propane
  参考文献：
  名称：

  Synthesis of novel cationic cardiolipin analogues for the optimal delivery of therapeutic agents

  摘要：

  A novel approach was developed to synthesize cardiolipin analogues containing two quaternary ammonium groups With tetraalkyl chain retaining 'glycerol' moiety, the central core of the molecule. The analogues were synthesized with or without spacer and/or lipid chain length with saturation to tailor lipid-based formulations of therapeutic agents for optimal delivery to target sites. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.044

文献信息

• Cationic cardiolipin analoges and its use thereof
  申请人：Ahmad U. Moghis

  公开号：US20050277611A1

  公开（公告）日：2005-12-15

  The invention provides cationic cardiolipin compounds, and methods for synthesizing and using them in liposomal formulation, gene transfection, etc. In particular, the invention provides liposomes comprising cationic cardiolipin analog, pharmaceutical compositions comprising cationic cardiolipin analogs, and methods of using such liposomes and compositions, in delivering active pharmaceutical agents to treat human and animal diseases and/or in diagnostic assays.

  本发明提供了阳离子心磷脂化合物以及其合成和在脂质体制剂、基因转染等方面的使用方法。特别地，本发明提供了含阳离子心磷脂类似物的脂质体、含阳离子心磷脂类似物的药物组合物以及使用这些脂质体和组合物的方法，用于传递活性药物治疗人类和动物疾病和/或诊断测定。
• CATIONIC CARDIOLIPIN ANALOGS AND USE THEREOF
  申请人：Neopharm, Inc.

  公开号：EP1558562A1

  公开（公告）日：2005-08-03
• LIPID COMPOSITIONS AND USE THEREOF
  申请人：Neopharm, Inc.

  公开号：EP1742661A2

  公开（公告）日：2007-01-17
• [EN] CATIONIC CARDIOLIPIN ANALOGS AND USE THEREOF<br/>[FR] ANALOGUES DE CARDIOLIPINE CATIONIQUES ET UTILISATION DE CEUX-CI
  申请人：NEOPHARM INC

  公开号：WO2004035523A1

  公开（公告）日：2004-04-29

  The invention provides cationic cardiolipin compounds, and methods for synthesizing and using them in liposomal formulation, gene transfection, etc. In particular, the invention provides liposomes comprising cationic cardiolipin analog, pharmaceutical compositions comprising cationic cardiolipin analogs, and methods of using such liposomes and compositions, in delivering active pharmaceutical agents to treat human and animal diseases and/or in diagnostic assays.
• [EN] LIPID COMPOSITIONS AND USE THEREOF<br/>[FR] COMPOSITIONS LIPIDIQUES ET LEURS UTILISATIONS
  申请人：NEOPHARM INC

  公开号：WO2005067632A2

  公开（公告）日：2005-07-28

  The invention provides a composition suitable for use as a transfection agent, comprising a cationic cardiolipin analogue and, another lipid species. The composition of the present invention can facilitate transfection of a wide variety of polynucleotide species (e.g., oligodeoxyribonucleotides, plasmids, RNAi species, etc.). Moreover, the transfection agent of the present invention is effective in promoting transfection of primary cell cultures as well as transformed cells. Also, the inventive transfection agent is suitable for use both in vitro and in vivo. The inventive composition has additional uses as well, such as delivery of a variety of active agents, dermatological and cosmetic uses, and uses in agriculture. The invention further provides a method of introducing an active agent into a cell by contacting the cell with the inventive composition. The invention further provides a method of inhibiting the growth of neoplastic cells and a method of treating a patient suffering from a neoplastic disease by employing the inventive composition, wherein an active agent is an antineoplastic agent. The invention further provides a method for validating a genetic target, comprising (a) administering to a cell a composition comprising a cationic liposome and a siRNA, whereby the siRNA enters the cell inhibits the expression of a gene within the cell and (b) assaying for the inhibition of the gene. The method also provides a fluorescent/ luminescent cationic cardiolipin analogue and compositions including such analogues. Using a cationic cardiolipin analogue, the invention provides a method of tracking the migration of a lipid substance within an animal.