N1,N2,N3,N4,N5-penta(tert-butoxycarbonyl)-pentaethylenehexamine | 284035-17-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N1,N2,N3,N4,N5-penta(tert-butoxycarbonyl)-pentaethylenehexamine
• 英文别名: N¹,N²,N³,N⁴,N⁵-penta(tert-butoxycarbonyl)-pentaethylenehexamine；(N1,N3,N6,N9,N12-penta-tert-butoxycarbonyl)-1,14-di-amino-3,6,9,12-tetraazatetradecane
• CAS: 284035-17-2
• 化学式: C₃₅H₆₈N₆O₁₀
• 分子量: 732.959
• InChiKey: NKWXZFDZIGEQRY-UHFFFAOYSA-N

物化性质

• 沸点：
  752.5±60.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  51.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  182.51
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N1,N2,N3,N4,N5-penta(tert-butoxycarbonyl)-pentaethylenehexamine 在 TEA 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 [2-(2-{2-[2-(2-Amino-ethylamino)-ethylamino]-ethylamino}-ethylamino)-ethyl]-carbamic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Synthesis of cholesterol-polyamine carbamates: pKa studies and condensation of calf thymus DNA

  摘要：

  我们制备了新型胆固醇-多胺氨基甲酸酯，并通过电位计测定了它们与最多五个氨基官能团取代的共轭物的 pKas，还测定了它们与小牛胸腺 DNA 的结合亲和力；这些多胺氨基甲酸酯是基因递送（脂质体感染）方面脂质体形成的模型，而脂质体感染是基因治疗的关键第一步。

  DOI：

  10.1039/a803284j
• 作为产物：
  描述：

  {2-[tert-Butoxycarbonyl-(2-tert-butoxycarbonylamino-ethyl)-amino]-ethyl}-{2-[tert-butoxycarbonyl-(2-{tert-butoxycarbonyl-[2-(2,2,2-trifluoro-acetylamino)-ethyl]-amino}-ethyl)-amino]-ethyl}-carbamic acid tert-butyl ester 在 氨 、 水 作用下， 以 甲醇 为溶剂， 生成 N1,N2,N3,N4,N5-penta(tert-butoxycarbonyl)-pentaethylenehexamine
  参考文献：
  名称：

  Synthesis of cholesterol-polyamine carbamates: pKa studies and condensation of calf thymus DNA

  摘要：

  我们制备了新型胆固醇-多胺氨基甲酸酯，并通过电位计测定了它们与最多五个氨基官能团取代的共轭物的 pKas，还测定了它们与小牛胸腺 DNA 的结合亲和力；这些多胺氨基甲酸酯是基因递送（脂质体感染）方面脂质体形成的模型，而脂质体感染是基因治疗的关键第一步。

  DOI：

  10.1039/a803284j

文献信息

• Synthesis and cellular studies of polyamine conjugates of a mercaptomethyl–carboranylporphyrin
  作者：N.V.S. Dinesh K. Bhupathiraju、M. Graça H. Vicente

  DOI：10.1016/j.bmc.2012.11.007

  日期：2013.1

  Seven polyamine conjugates of a tri(p-carboranylmethylthio)tetrafluorophenylporphyrin were prepared in high yields by sequential substitution of the p-phenyl fluoride of tetrakis(pentafluorophenyl) porphyrin (TPPF), and investigated as boron delivery agents for boron neutron capture therapy (BNCT). The polyamines used were derivatives of the natural-occurring spermine with different lengths of the carbon chains, terminal primary amine groups and, in two of the conjugates, additional aminoethyl moieties. A tri(polyethylene glycol) conjugate was also synthesized for comparison purposes. The polyamine conjugates showed low dark cytotoxicity (IC50 >400 mu M) and low phototoxicity (IC50 >40 mu M at 1.5 J/cm(2)). All polyamine conjugates, with one exception, showed higher uptake into human glioma T98G cells (up to 12-fold) than the PEG conjugate, and localized preferentially in the cell ER, Golgi and the lysosomes. Our results show that spermine derivatives can serve as effective carriers of boronated porphyrins for the BNCT of tumors. (C) 2012 Elsevier Ltd. All rights reserved.
• Polycationic β-Cyclodextrin “Click Clusters”:  Monodisperse and Versatile Scaffolds for Nucleic Acid Delivery
  作者：Sathya Srinivasachari、Katye M. Fichter、Theresa M. Reineke

  DOI：10.1021/ja074597v

  日期：2008.4.1

  Herein, a novel series of multivalent polycationic beta-cycloclextrin "click clusters" with discrete molecular weight have been synthesized, characterized, and examined as therapeutic pDNA carriers. The materials were creatively designed based on a beta-cyclodextrin core to impart a biocompatible multivalent architecture and oligoethyleneamine arms to facilitate pDNA binding, encapsulation, and cellular uptake. An acetylated-per-azido-beta-cyclodextrin (4) was reacted with series of alkyne dendrons (7a-e) (containing one to five ethyleneamine units) using copper-catalyzed 1,3-dipolar cycloaddition, to form a series of click clusters (9a-e) bearing 1,2,3-triazole linkers. Gel electrophoresis experiments, dynamic light scattering, and transmission electron microscopy revealed that the macromolecules bind and compact pDNA into spherical nanoparticles in the size range of 80-130 nm. The polycations protect pDNA against nuclease degradation, where structures 9c, 9d, and 9e did not allow pDNA degradation in the presence of serum for up to 48 h. The cellular uptake profiles were evaluated in Opti-MEM and demonstrate that all the click clusters efficiently deliver Cy5-labeled pDNA into HeLa and H9c2 (2-1) cells, and compounds 9d and 9e yielded efficacy similar to that of the positive controls, Jet-PEI and Superfect. Furthermore, the luciferase gene delivery experiments revealed that the level of reporter gene expression increased with an increase in oligoethyleneamine number within the cluster arms. The cytotoxicity profiles of these materials were evaluated by protein, MTT, and LDH assays, which demonstrate that all the click clusters remain nontoxic within the expected dosage range while the positive controls, Jet PEI and Superfect, were highly cytotoxic. In particular, 9d and 9e were the most effective and promising polycationic vehicles to be further optimized for future systemic delivery experiments.