3-[3-[3-[3-[Bis[3-[bis(2-cyanoethyl)amino]propyl]amino]propyl-[2-(4-hydroxyphenyl)ethyl]amino]propyl-[3-[bis(2-cyanoethyl)amino]propyl]amino]propyl-(2-cyanoethyl)amino]propanenitrile | 1300556-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[3-[3-[3-[Bis[3-[bis(2-cyanoethyl)amino]propyl]amino]propyl-[2-(4-hydroxyphenyl)ethyl]amino]propyl-[3-[bis(2-cyanoethyl)amino]propyl]amino]propyl-(2-cyanoethyl)amino]propanenitrile
• 英文别名: 3-[3-[3-[3-[bis[3-[bis(2-cyanoethyl)amino]propyl]amino]propyl-[2-(4-hydroxyphenyl)ethyl]amino]propyl-[3-[bis(2-cyanoethyl)amino]propyl]amino]propyl-(2-cyanoethyl)amino]propanenitrile
• CAS: 1300556-06-2
• 化学式: C₅₀H₇₇N₁₅O
• 分子量: 904.261
• InChiKey: UGFRQFPMUOCNOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  66
• 可旋转键数：
  43
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  233
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3-[3-[3-[3-[Bis[3-[bis(2-cyanoethyl)amino]propyl]amino]propyl-[2-(4-hydroxyphenyl)ethyl]amino]propyl-[3-[bis(2-cyanoethyl)amino]propyl]amino]propyl-(2-cyanoethyl)amino]propanenitrile 在 三乙基硅烷 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 48.0h， 生成 3-[3-[3-[3-[Bis[3-[bis(2-cyanoethyl)amino]propyl]amino]propyl-[2-[4-[2-[2-[2-(2-sulfanylethoxy)ethoxy]ethoxy]ethoxy]phenyl]ethyl]amino]propyl-[3-[bis(2-cyanoethyl)amino]propyl]amino]propyl-(2-cyanoethyl)amino]propanenitrile
  参考文献：
  名称：

  A new poly(propylene imine) dendron as potential convenient building-block in the construction of multifunctional systems

  摘要：

  The synthesis of a novel third generation poly(propylene imine) dendron (PPI dendron) is described herein. The dendritic focal point was attached to a tetraethylene glycol spacer that was terminated with a Tmob-protected thiol in order to both avoid any side-reaction during functionalization of dendritic branches as well as enable convenient integration of the dendron into diverse complex systems. The protonation of the final PPI dendron at pH 4-5 is predicted to induce lysosomal degradation through the proton-sponge effect, and therefore enable cytosolic release. These features make the prepared dendron a very convenient building-block for use in the construction of larger systems, such as multifunctional drug delivery vehicles. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.070
• 作为产物：
  描述：

  3,3'-((4-hydroxyphenethyl)azanediyl)dipropanenitrile 在 dimethyl sulfide borane 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 96.0h， 生成 3-[3-[3-[3-[Bis[3-[bis(2-cyanoethyl)amino]propyl]amino]propyl-[2-(4-hydroxyphenyl)ethyl]amino]propyl-[3-[bis(2-cyanoethyl)amino]propyl]amino]propyl-(2-cyanoethyl)amino]propanenitrile
  参考文献：
  名称：

  A new poly(propylene imine) dendron as potential convenient building-block in the construction of multifunctional systems

  摘要：

  The synthesis of a novel third generation poly(propylene imine) dendron (PPI dendron) is described herein. The dendritic focal point was attached to a tetraethylene glycol spacer that was terminated with a Tmob-protected thiol in order to both avoid any side-reaction during functionalization of dendritic branches as well as enable convenient integration of the dendron into diverse complex systems. The protonation of the final PPI dendron at pH 4-5 is predicted to induce lysosomal degradation through the proton-sponge effect, and therefore enable cytosolic release. These features make the prepared dendron a very convenient building-block for use in the construction of larger systems, such as multifunctional drug delivery vehicles. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.070

文献信息

• Set of Highly Stable Amine- and Carboxylate-Terminated Dendronized Au Nanoparticles with Dense Coating and Nontoxic Mixed-Dendronized Form
  作者：Arunendra Saha Ray、William E. Ghann、Phoebe S. Tsoi、Brian Szychowski、Lance T. Dockery、Yewon J. Pak、Wenjing Li、Maureen A. Kane、Peter Swaan、Marie-Christine Daniel

  DOI：10.1021/acs.langmuir.8b03196

  日期：2019.3.5

  formation of a highly stable, dendronized gold nanoparticle (AuNP)-based drug delivery platform is described herein. The AuNP-based platform is composed of three complementary parts: (i) a 15 nm AuNP core, (ii) a heterofunctional thioctic acid-terminated tetraethylene glycol spacer, and (iii) a third-generation PPI dendron with a unique protonation profile and diverse end-group functionalization that allows

  本文描述了克级的新型聚（亚丙基亚胺）（PPI）树突的合成及其在形成高度稳定的，基于树突化的金纳米颗粒（AuNP）的药物递送平台中的用途。基于AuNP的平台由三个互补部分组成：（i）15 nm AuNP核，（ii）杂官能硫辛酸封端的四甘醇间隔基，以及（iii）具有独特质子化特征的第三代PPI树突和多样化的端基功能化，可以进一步衍生化。所制备的树突状AuNPs能够经受数轮冻干循环而没有聚集迹象，在磷酸盐缓冲液和汉克斯缓冲液以及血清中稳定，并且对谷胱甘肽交换反应具有抗降解性。这个纳米载体平台显示出致密的涂层，具有超过1400个树突/ AuNP，这将实现非常高的有效载荷。此外，虽然预期胺端基的AuNPs从1nM的NP浓度显示出对MCF-7乳腺癌细胞系的细胞毒性，但有趣的是，混合的单层AuNPs（涂有40/60胺/羧酸根树突）没有任何毒性迹象。浓度高达15 nM，类似于羧酸盐封端的AuNPs。所述的
• Gold nanoparticle-cored poly(propyleneimine) dendrimers as a new platform for multifunctional drug delivery systems
  作者：Marie-Christine Daniel、Margaret E. Grow、Hongmu Pan、Maria Bednarek、William E. Ghann、Kara Zabetakis、Joseph Cornish

  DOI：10.1039/c1nj20206e

  日期：——

  Two poly(propyleneimine) dendrons (PPI dendrons) of third generation, containing eight branches (nitriles or primary amines) and having tyramine as the focal point, were prepared. A tetraethylene glycol spacer (TEG), terminated by a protected thiol group, was attached to their focal points. The obtained TEG–PPI dendrons were successfully used to cap 18 nm spherical gold nanoparticles, with no need for intermediate thioctic acid exchange of citrate, as previously reported for non-anionic ligands. The novel gold nanoparticle-cored PPI dendrimers were characterized by UV-visible and FT-IR spectroscopic techniques, dynamic light scattering (DLS), zeta-potential and transmission electron microscopy (TEM). Importantly, the amine terminated gold nanoparticle-cored PPI dendrimer showed great stability in PBS buffer, as well as in the presence of a salt, and they did not show any sign of degradation after freeze-drying. Also, this new type of PPI dendrimer was found to protonate at pH around 4.5 for their internal tertiary amines. The latter being present in large numbers on each gold nanoparticle, their protonation at pH below 5 will produce a proton-sponge effect, which plays a crucial role in lysosomal escape during drug delivery.

  我们制备了两种第三代聚（丙烯酰亚胺）树枝状化合物（PPI 树枝状化合物），它们含有八个分支（腈或伯胺），以酪胺为焦点。在这些树枝状化合物的焦点上连接了一个以受保护的硫醇基团为末端的四甘醇间隔物（TEG）。所获得的 TEG-PPI 树枝状化合物被成功地用于 18 纳米球形金纳米粒子的封盖，而无需像之前报道的非阴离子配体那样进行中间硫代柠檬酸交换。通过紫外-可见光和傅立叶变换红外光谱技术、动态光散射（DLS）、ZETA 电位和透射电子显微镜（TEM）对新型金纳米粒子包覆 PPI 树状分子进行了表征。重要的是，胺端金纳米粒子包覆的 PPI 树状聚合物在 PBS 缓冲液和盐存在下都表现出了极高的稳定性，而且在冷冻干燥后也没有出现任何降解迹象。此外，还发现这种新型 PPI 树枝状聚合物在 pH 值为 4.5 左右时，其内部的叔胺会发生质子化。后者大量存在于每个金纳米粒子上，在 pH 值低于 5 时，它们的质子化会产生质子海绵效应，这在给药过程中溶酶体逸出方面起着至关重要的作用。
• A new poly(propylene imine) dendron as potential convenient building-block in the construction of multifunctional systems
  作者：Hongmu Pan、Margaret E. Grow、Orla Wilson、Marie-Christine Daniel

  DOI：10.1016/j.tet.2013.01.070

  日期：2013.4

  The synthesis of a novel third generation poly(propylene imine) dendron (PPI dendron) is described herein. The dendritic focal point was attached to a tetraethylene glycol spacer that was terminated with a Tmob-protected thiol in order to both avoid any side-reaction during functionalization of dendritic branches as well as enable convenient integration of the dendron into diverse complex systems. The protonation of the final PPI dendron at pH 4-5 is predicted to induce lysosomal degradation through the proton-sponge effect, and therefore enable cytosolic release. These features make the prepared dendron a very convenient building-block for use in the construction of larger systems, such as multifunctional drug delivery vehicles. (C) 2013 Elsevier Ltd. All rights reserved.