1-[N,N-bis(3-aminopropyl)-1,4-butanediamine]dodecane

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-[N,N-bis(3-aminopropyl)-1,4-butanediamine]dodecane
• 英文别名: N-(3-aminopropyl)-N'-[3-(dodecylamino)propyl]butane-1,4-diamine
• 化学式: C₂₂H₅₀N₄
• 分子量: 370.666
• InChiKey: NGVSRGLLNFKBEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  精胺 、 溴代十二烷 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以1.2 g的产率得到1-[N,N-bis(3-aminopropyl)-1,4-butanediamine]dodecane
  参考文献：
  名称：

  Highly Hydrophilic Fused Aggregates (Microsponges) from a C12 Spermine Bolaamphiphile

  摘要：

  Bolaamphiphiles consist of two hydrophilic headgroups joined by a hydrophobic linker. They are known to self-assemble into vesicles, micelles, tubules and fibers. Here we report on the self-assembly of a 1,12-[N,N-bis(3-aminopropyl)-1,4-butane diamine] dodecane (12G1) in aqueous media into discrete nonbilayer nanoparticles and unusual fused highly hydrated sponge like structures. 12G1, 1,10-[N,N-bis(3-aminopropyl)1,4-butane diamine] decane (10G1), 1,8-[N,N-bis(3-aminopropyl)-1,4-butane diamine] octane (8G1), and 1-[N,N-bis(3-aminopropyl)-1,4-butane diamine] dodecane (12G0) were synthesized and their self-assembly studied. 12G0 was relatively insoluble in water and multilamellar vesicles were produced with this amphiphile and cholesterol. While no aggregation in aqueous media was recorded for either 10G1 or 8G1 up to a concentration of 20 mM, aggregation of 12G1 molecules was seen to take place at an aqueous concentration of 1.75 mM as determined using various fluorescent and colorimetric probes and surface tension measurements. Electron microscopy images revealed that 12G1 formed monolayer vesicles of 20 nm in size at a concentration of 2.6 mM and even larger fused aggregates when the concentration was increased to 35 mM. Fusion resulted from the bridging of vesicles by the bolaamphiphile molecules. 12G1 aggregates encapsulated 23X more low molecular weight (4kD) FITC-dextran than high (250kD) molecular weight FITC-dextran, an indication of the limited volume of the hydrophilic domains. 12G1 also encapsulated 137X more 4kD FITC-dextran than was encapsulated by conventional sorbitan monostearate vesicles. We conclude that highly hydrated aggregates consisting of fused monolayer vesicles with small discrete hydrophilic domains in a sponge like structure may be formed by the self-assembly of bolaamphiphiles.

  DOI：

  10.1021/jp0372237

文献信息

• Multifunctional molecular complexes for gene transfer to cells
  申请人：American Home Products Corporation

  公开号：US20020155607A1

  公开（公告）日：2002-10-24

  A multifunctional molecular complex for the transfer of a nucleic acid composition to a target cell is provided The complex is comprised of A) said nucleic acid composition and B) a transfer moiety comprising 1) one or more cationic polyamines bound to said nucleic acid composition, 2) one or more endosome membrane disrupting components attached to at least one nitrogen of the polyamine and 3) one or more receptor specific binding components.

  提供了一种用于将核酸组合物转移至靶细胞的多功能分子复合物。该复合物由A）所述核酸组合物和B）转移基团组成，其中包括1）与所述核酸组合物结合的一个或多个阳离子聚胺，2）连接到聚胺的至少一个氮的一个或多个内体膜破坏成分，以及3）一个或多个受体特异性结合成分。
• MULTIFUNCTIONAL MOLECULAR COMPLEXES FOR GENE TRANSFER TO CELLS
  申请人：Wyeth

  公开号：EP0789708B1

  公开（公告）日：2004-11-03
• US6379965B1
  申请人：——

  公开号：US6379965B1

  公开（公告）日：2002-04-30
• US7202227B2
  申请人：——

  公开号：US7202227B2

  公开（公告）日：2007-04-10
• [EN] MULTIFUNCTIONAL MOLECULAR COMPLEXES FOR GENE TRANSFER TO CELLS<br/>[FR] COMPLEXES MOLECULAIRES MULTIFONCTIONNELS POUR TRANSFERT DE GENES VERS DES CELLULES
  申请人：APOLLON, INC.

  公开号：WO1996010038A1

  公开（公告）日：1996-04-04

  (EN) A multifunctional molecular complex for the transfer of a nucleic acid composition to a target cell is provided. The complex is comprised of A) said nucleic acid composition and B) a transfer moiety comprising 1) one or more cationic polyamines bound to said nucleic acid composition, 2) one or more endosome membrane disrupting components attached to at least one nitrogen of the polyamine and 3) one or more receptor specific binding components.(FR) Complexe moléculaire multifonctionnel pour le transfert d'une composition d'acide nucléique sur une cellule cible. Le complexe est constitué de A) la composition d'acide nucléique et B) une fraction de transfert renfermant 1) une ou plusieurs polyamines cationiques liées à la composition d'acide nucléique précitée, 2) un ou plusieurs composants de rupture de membrane endosome attachés à au moins un élément azote de la polyamine et (3) un ou plusieurs composants de liaison spécifique du récepteur.