2-aminoethyl-[2,3-bis[(Z)-octadec-9-enoxy]propyl]-dimethylazanium | 714192-23-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-aminoethyl-[2,3-bis[(Z)-octadec-9-enoxy]propyl]-dimethylazanium
• CAS: 714192-23-1
• 化学式: C₄₃H₈₇N₂O₂
• 分子量: 664.176
• InChiKey: VHAJDBUBFGEGMI-WRBBJXAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.9
• 重原子数：
  47
• 可旋转键数：
  39
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-aminoethyl-[2,3-bis[(Z)-octadec-9-enoxy]propyl]-dimethylazanium 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 2,3-dioleoyloxy-N-[2-(spermine-carboxamido)ethyl]-N,N-dimethyl-1-propanaminum chloride
  参考文献：
  名称：

  一种高效合成阳离子脂质 DOSPA 的方法

  摘要：

  已经开发了一种高效的合成阳离子脂质的策略，N-[2-({2,5-双[(3-氨基丙基)氨基]-1-氧代戊基}氨基)乙基]-N,N-二甲基-2,3-双[(1-oxo-9-octadecenyl)oxy] 与氯化氢的盐 (DOSPA)。它涉及在标准偶联剂存在下连接阳离子头基和疏水部分。

  DOI：

  10.1055/s-2006-949636
• 作为产物：
  描述：

  3-二甲胺基-1,2-丙二醇 在 sodium hydride 、 肼 作用下， 以 甲醇 、 xylene 为溶剂， 反应 39.0h， 生成 2-aminoethyl-[2,3-bis[(Z)-octadec-9-enoxy]propyl]-dimethylazanium
  参考文献：
  名称：

  一种高效合成阳离子脂质 DOSPA 的方法

  摘要：

  已经开发了一种高效的合成阳离子脂质的策略，N-[2-({2,5-双[(3-氨基丙基)氨基]-1-氧代戊基}氨基)乙基]-N,N-二甲基-2,3-双[(1-oxo-9-octadecenyl)oxy] 与氯化氢的盐 (DOSPA)。它涉及在标准偶联剂存在下连接阳离子头基和疏水部分。

  DOI：

  10.1055/s-2006-949636

文献信息

• Delivery of nucleic acid-like compounds
  申请人：——

  公开号：US20040037874A1

  公开（公告）日：2004-02-26

  A process for preparing a microparticulate complex is provided. The process comprises (a) combining a particle-forming component (“PFC”) and a nucleic acid-like component (“NAC”) in a monophasic composition comprising water and a water-miscible, organic solvent to form a mixture wherein the PFC and the NAC are independently molecularly or micellarly soluble in the aqueous/organic solvent system, and (b) reducing the amount of the organic solvent in the mixture. This effects formation of the microparticulate complex of the NAC and the PFC. Also provided is a microparticulate complex that comprises a particle-forming component complexed to a nucleic acid-like component forming an approximately spherical particle, wherein the particle-forming component encloses an interior of the particle containing the nucleic acid-like component and the so-enclosed interior volume has less than about 50% (preferably less than 20%) of the volume containing free water. Also disclosed composition comprising water and particles of the microparticulate complex. According to the invention a nucleic acid-like component is delivered to a cell by (a) contacting the cell with a composition comprising water and the microparticulate complex, and (b) maintaining the contact for a time sufficient to allow the nucleic acid-based moiety to enter the cell. A therapeutic nucleic acid-like component is delivered into a patient in need thereof by administering a composition comprising water and particles of the microparticulate complex. Also disclosed is a charge-changing composition represented by the formula A-X-B, wherein X represents a chemical bond capable of irreversible dissociation in reaction to a factor in a physiological or bioprocess environment; A represents a molecular moiety that upon dissociation of the bond X produces a ionically charged product; and B represents a molecular moiety, which upon the dissociation of bond X, separates from the composition leaving the remaining ionically charged product more positive than that of A-X-B itself.

  提供了一种制备微粒复合物的工艺。该工艺包括：(a) 将微粒形成成分（"PFC"）和类核酸成分（"NAC"）结合在由水和水混溶有机溶剂组成的单相组合物中，形成混合物，其中 PFC 和 NAC 在水/有机溶剂体系中各自具有分子或胶束溶解性；(b) 减少混合物中有机溶剂的用量。这将影响 NAC 和 PFC 微颗粒复合物的形成。还提供了一种微粒复合物，它包括与类核酸成分复配形成近似球形颗粒的颗粒形成成分，其中颗粒形成成分包围了含有类核酸成分的颗粒内部，而如此包围的内部体积中含有自由水的体积小于约 50%（优选小于 20%）。还公开了包含水和微粒复合物颗粒的组合物。根据本发明，可通过以下方式将核酸类成分输送到细胞中：(a) 使细胞与包含水和微粒复合物的组合物接触，(b) 保持接触足够长的时间，使核酸类分子进入细胞。通过施用由水和微粒复合物颗粒组成的组合物，将治疗性核酸样成分输送给有需要的患者。还公开了一种电荷改变组合物，由式 A-X-B 表示，其中 X 代表一种化学键，在与生理或生物过程环境中的某种因素发生反应时能够不可逆转地解离；A 代表一种分子基团，在键 X 解离时产生一种带离子电荷的产物；B 代表一种分子基团，在键 X 解离时从组合物中分离出来，剩下的带离子电荷的产物比 A-X-B 本身更正向。
• DELIVERY OF NUCLEIC ACID-LIKE COMPOUNDS
  申请人：California Pacific Medical Center

  公开号：EP1509203B1

  公开（公告）日：2016-04-13
• US8496961B2
  申请人：——

  公开号：US8496961B2

  公开（公告）日：2013-07-30
• US8883200B2
  申请人：——

  公开号：US8883200B2

  公开（公告）日：2014-11-11
• [EN] DELIVERY OF NUCLEIC ACID-LIKE COMPOUNDS<br/>[FR] DISTRIBUTION DE COMPOSES DU TYPE ACIDES NUCLEIQUES
  申请人：CALIFORNIA PACIFIC MED CENTER

  公开号：WO2003097805A2

  公开（公告）日：2003-11-27

  A process for preparing a microparticulate complex is provided. The process comprises: a) combining a particle-forming component ('PFC') and a nucleic acid-like component ('NAC') in a monophasic composition comprising water and a water-miscible, organic solvent to form a mixture wherein the PFC and the NAC are independently molecularly or micellarly soluble in the aqueous/organic solvent system, and b) reducing the amount of the organic solvent in the mixture. This effects formation of the microparticulate complex of the NAC and the PFC. Also provided is a microparticulate complex that comprises a particle-forming component complexed to a nucleic acid-like component forming an approximately spherical particle, wherein the particle-forming component encloses an interior of the particle containing the nucleic acid-like component and the so-enclosed interior volume has less than about 50 % (preferably less than 20 %) of the volume containing free water. Also disclosed composition comprising water and particles of the microparticulate complex. According to the invention a nucleic acid-like is component is delivered to a cell by (a) contacting the cell with a composition comprising water and the microparticulate complex, and (b) maintaining the contact for a time sufficient to allow the nucleic acid-based moiety to enter the cell. A therapeutic nucleic acid-like component is delivered into a patient in need thereof by administering a composition comprising water and particles of the microparticulate complex. Also disclosed is a charge-changing composition represented by the formula A-X-B, wherein X represents a chemical bond capable of irreversible dissociation in reaction to a factor in a physiological or bioprocess environment; A represents a molecular moiety that upon dissociation of the bond X produces a ionically charged product; and B represents a molecular moiety, which upon the dissociation of bond X, separates from the composition leaving the remaining ionically charged product more positive than that of A-X-B itself.