di-tert-butyl (((tert-butoxycarbonyl)azanediyl)bis(ethane-2,1-diyl))bis((2-aminoethyl)carbamate) | 556082-09-8

• 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: di-tert-butyl (((tert-butoxycarbonyl)azanediyl)bis(ethane-2,1-diyl))bis((2-aminoethyl)carbamate)
• 英文别名: Tepa(hbbbh)；tert-butyl N,N-bis[2-[2-aminoethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethyl]carbamate
• CAS: 556082-09-8
• 化学式: C₂₃H₄₇N₅O₆
• 分子量: 489.656
• InChiKey: LKWDYNQTBFTICA-UHFFFAOYSA-N

物化性质

• 沸点：
  575.3±50.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  34
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  di-tert-butyl (((tert-butoxycarbonyl)azanediyl)bis(ethane-2,1-diyl))bis((2-aminoethyl)carbamate) 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 101.0h， 生成 N¹-(2-aminomethyl)-N²[2-{[2-(anthrylmethyl)aminoethyl]amino}ethyl]ethane-1,2-diamine
  参考文献：
  名称：

  在没有外部干预的情况下沿轨道非定向行走的小分子

  摘要：

  轻旅的电荷：一个分子能够在五个立足的五亚乙基亚胺轨道上来回走动，而无需外部干预。一维随机游走具有高度的过程性（平均步数为530），并且相邻胺基之间的交换以逐步方式进行。助行器在行走时执行一个简单的任务：消除位于轨道一端的蒽基团的荧光。

  DOI：

  10.1002/anie.201200822
• 作为产物：
  描述：

  tetraethylenepentamine pentahydrochloride 在 TEA 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 17.5h， 生成 di-tert-butyl (((tert-butoxycarbonyl)azanediyl)bis(ethane-2,1-diyl))bis((2-aminoethyl)carbamate)
  参考文献：
  名称：

  Trehalose Click Polymers Inhibit Nanoparticle Aggregation and Promote pDNA Delivery in Serum

  摘要：

  Herein, three new glycopolymers have been synthesized via "click polymerization" to promote nucleic acid delivery in the presence of biological media containing serum. These structures were designed to contain a trehalose moiety to promote biocompatibility, water solubility, and stability against aggregation, amide-triazole groups to enhance DNA binding affinity, and an oligoamine unit to facilitate DNA encapsulation, phosphate neutralization, and interactions with cell surfaces. A 2,3,4,2', 3', 4'-hexa-O-acetyl-6,6'-diazido-6,6'-dideoxy-(D)-trehalose (4) monomer was polymerized via copper(I)-catalyzed azide-alkyne cycloaddition with a series of dialkyne-amide comonomers that contain either one, two, or three Boc-protected secondary amines (7a, 7b, or 7c, respectively). After deprotection, three water-soluble polycations (9a, 9b, or 9c) were obtained with similar degrees of polymerization (n = 56-61) to elucidate the role of amine number on nucleic acid binding, complex formation, stability, and cellular delivery. Gel electrophoresis and ethidium bromide experiments showed that 9a-9c associated with plasmid DNA (pDNA) and formed complexes (polyplexes) at N/P ratios dependent on the amine number. TEM experiments revealed that 9a-9c polyplexes were small (50-120 nm) and had morphologies (spherical and rodlike) associated with the polymer chain stiffness. Dynamic light scattering studies in the presence of media containing serum demonstrated that 9c polyplexes had a low degree of flocculation, whereas 9a and 9b polyplexesd aggregate rapidly. Further biological studies revealed that these structures were biocompatible and deliver pDNA into HeLa cells. Particularly, 9c polyplexes promoted high delivery efficacy and gene expression profiles in the presence of serum.

  DOI：

  10.1021/ja0585580

文献信息

• A Facile Synthesis of Selectively Protected Linear Oligoamines
  作者：Simona Koščová、Miloš Buděšínský、Jana Hodačová

  DOI：10.1135/cccc20030744

  日期：——

  A convenient multi-gram preparative method for the synthesis of linear oligoamines having the terminal primary amino groups unprotected and the central secondary amino functions protected with tert-butoxycarbonyl groups is presented. At the same time, simple one-pot preparation of the α,ω-bis(trifluoroacetamide) intermediates 2 has been developed. NMR spectra of the novel selectively protected oligoamines are also discussed.

  一种方便的多克隆制备方法用于合成具有未保护的末端初级氨基团和中心次级氨基功能受到tert-丁氧羰基团保护的线性寡胺。同时，还开发了α，ω-双(三氟乙酰胺)中间体2的简单一锅制备方法。还讨论了新型选择性保护寡胺的NMR光谱。
• Polyethylenimine analogs for improved gene delivery: effect of the type of amino groups
  作者：Miao-Miao Xun、Ju-Hui Zhang、Yan-Hong Liu、Ji Zhang、Ya-Ping Xiao、Qian Guo、Shuo Li、Xiao-Qi Yu

  DOI：10.1039/c5ra23715g

  日期：——

  The 1°, 2° and 3° amine composition of PEI analogs could be easily adjusted by special synthetic method, and their effects on the gene transfection were studied.

  PEI类似物的1°、2°和3°胺组成可以通过特殊的合成方法轻松调整，并研究它们对基因转染的影响。
• Developing Bivalent Ligands to Target CUG Triplet Repeats, the Causative Agent of Myotonic Dystrophy Type 1
  作者：Amin Haghighat Jahromi、Yuan Fu、Kali A. Miller、Lien Nguyen、Long M. Luu、Anne M. Baranger、Steven C. Zimmerman

  DOI：10.1021/jm400794z

  日期：2013.12.12

  expanded CUG repeat transcript (CUGexp) is the causative agent of myotonic dystrophy type 1 (DM1) by sequestering muscleblind-like 1 protein (MBNL1), a regulator of alternative splicing. On the basis of a ligand (1) that was previously reported to be active in an in vitro assay, we present the synthesis of a small library containing 10 dimeric ligands (4–13) that differ in length, composition, and attachment

  扩展的 CUG 重复转录本 (CUG exp ) 是通过隔离肌盲样 1 蛋白 (MBNL1) 导致 1 型强直性肌营养不良 (DM1) 的病原体，MBNL1 是可变剪接的调节因子。基于先前报道在体外测定中具有活性的配体 ( 1 )，我们提出了一个包含 10个二聚配体 ( 4-13 )的小文库的合成，这些配体的长度、组成和附着点不同链接链。与寡醚接头相比，寡氨基接头对 CUG RNA 的亲和力更大，并且更有效。最有效的体外配体（9) 被证明是水溶性的并且具有细胞和细胞核渗透性，在 DM1 细胞模型中显示 MBNL1 核糖核病灶几乎完全分散。使用延时共聚焦荧光显微镜观察到9的生物活性的直接证据是其在单个活 DM1 模型细胞中分散核糖核病灶的能力。
• Novel Fmoc-Polyamino Acids for Solid-Phase Synthesis of Defined Polyamidoamines
  作者：David Schaffert、Naresh Badgujar、Ernst Wagner

  DOI：10.1021/ol200381z

  日期：2011.4.1

  A versatile solid-phase approach to sequence-defined polyamidoamines was developed. Four different Fmoc-polyamino acid building blocks were synthesized by selective protection of symmetrical oligoethylenimine precursors followed by introduction of a carboxylic acid handle using cyclic anhydrides and subsequent Fmoc-protection. The novel Fmoc-polyamino acids were used to construct polyamidoamines demonstrating

  开发了一种通用的固相方法，用于确定序列的聚酰胺胺。四种不同的Fmoc-聚氨基酸结构单元是通过对对称的低聚乙炔亚胺前体进行选择性保护，然后使用环酐引入羧酸的处理方法以及随后的Fmoc保护来合成的。新型Fmoc-聚氨基酸用于构建聚酰胺酰胺，证明与标准Fmoc反应条件完全相容。结构单元的直接合成和固相偶联反应的高效率使所定义的聚阳离子的多功能合成成为可能。
• Lanthanide-Containing Polycations for Monitoring Polyplex Dynamics via Lanthanide Resonance Energy Transfer
  作者：Sneha S. Kelkar、Lian Xue、S. Richard Turner、Theresa M. Reineke

  DOI：10.1021/bm401870z

  日期：2014.5.12

  hydrodynamic diameters around 50–80 nm. Lanthanide resonance energy transfer (LRET) was used to monitor polyplex association and dissociation. Polyplexes were formed using the donor–acceptor pair comprising of terbium-chelated polymer with five ethyleneamines within the repeat unit (6c-Tb) and tetramethyl rhodamine (TMR)-labeled pDNA. Association/dissociation in the presence of heparin and NaCl was monitored

  在过去的十年中，治疗学纳米材料出现了，它将治疗性递送和诊断成像结合在一起。这些材料提供了帮助诊断，跟踪治疗性生物分布以及监测药物释放的机会。我们已经开发了一系列含有低聚亚乙基胺的核酸输送聚合物，这些寡聚亚胺能够在生理pH下质子化（用于结合/压缩pDNA）和镧系元素螯合域，从而赋予诊断功能。通过多步方法制备二胺单体（包含3至6个Boc保护的亚乙基胺），该过程涉及对伯胺和仲胺的选择性保护和脱保护。然后通过低聚乙二胺与二亚乙基三胺五乙酸的双酐（DTPA-BA）的逐步增长聚合反应来合成聚合物结构，聚合度在18和24之间。进行聚合物与g和ter的螯合以提供MRI对比剂和发光特性。根据Horrock方程计算，发现所有的聚合物螯合物都可容纳约一个水配位位点，并且具有纵向弛豫性（[R 1（按每Gd计算）至少是临床对比剂Magnevist的两倍。所有的结构都形成了带有pDNA的多链体，具有高度正的ζ电势和大约50-80