1,16-bis(trifluoroacetyl)-1,4,7,10,13,16-hexaazahexadecane | 1372138-59-4

• 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: 1,16-bis(trifluoroacetyl)-1,4,7,10,13,16-hexaazahexadecane
• CAS: 1372138-59-4
• 化学式: C₁₄H₂₆F₆N₆O₂
• 分子量: 424.39
• InChiKey: SSESVCHNMHEMGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  28.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  106.32
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,16-bis(trifluoroacetyl)-1,4,7,10,13,16-hexaazahexadecane 在 甲醇 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 di-tert-butyl ethane-1,2-diylbis((2-((2-aminoethyl)(tert-butoxycarbonyl)amino)ethyl)carbamate)
  参考文献：
  名称：

  Effects of Trehalose Polycation End-Group Functionalization on Plasmid DNA Uptake and Transfection

  摘要：

  In this study, we have synthesized six analogs of a trehalose-pentaethylenehexamine glycopolymer (Tr4) that contain (1A) adamantane, (1B) carboxy, (1C) alkynyl-oligoethyleneamine, (1D) azido trehalose, (1E) octyl, or (1F) oligoethyleneamine end groups and evaluated the effects of polymer end group chemistry on the ability of these systems to bind, compact, and deliver pDNA to cultured HeLa cells. The polymers were synthesized in one pot azide-alkyne cycloaddition reactions with an adaptation of the Carothers equation for step growth polymerization to produce a series of polymers with similar degrees of polymerization. An excess of end-capping monomer was added at the end of the polymerizations to maximize functionalization efficiency, which was evaluated with GPC, NMR, and MALDI-TOF. The polymers were all found to bind and compact pDNA at similarly low N/P ratios and form polyplexes with plasmid DNA. The effects of the different end group structures were most evident in the polyplex internalization and transfection assays in the presence of serum as determined by flow cytometry and luciferase gene expression, respectively. The Tr4 polymers end capped with carboxyl groups (1B) (N/P = 7), octyne (1E) (N/P = 7), and oligoethyleneamine (1F) (N/P = 7), were taken into cells as polyplex and exhibited the highest levels of fluorescence, resulting from labeled plasmid. Similarly, the polymers end-functionalized with carboxyl groups (1E at N/P = 7), octyl groups (1E at N/P = 15), and in particular oligoethyleneamine groups (1F at N/P = 15) yielded dramatically higher reporter gene expression in the presence of serum. This study yields insight into how very subtle structural changes in polymer chemistry, such as end groups can yield very significant differences in the biological delivery efficiency and transgene expression of polymers used for pDNA delivery.

  DOI：

  10.1021/bm300471n
• 作为产物：
  描述：

  三氟乙酸乙酯 、 五乙烯六胺 以 甲醇 为溶剂， 反应 18.0h， 生成 1,16-bis(trifluoroacetyl)-1,4,7,10,13,16-hexaazahexadecane
  参考文献：
  名称：

  尿素低聚物中远程继电器极性开关介导的配体的可逆捕获和释放

  摘要：

  合成了以连续、可切换的氢键链为特征的乙烯桥接低聚脲，并带有一个用于氢键接受配体（氧化膦）的结合位点（N,N'-二取代脲）。当结合位点位于氢键供体末端时，这些寡聚体显示出比相同结合位点位于氢键接受末端时更强的配体结合。远离结合位点末端的酸性基团允许氢键极性，因此配体结合能力，可以通过去质子化/再质子化循环远程控制。碱基的添加会引起远程构象变化，该变化通过多达五个脲键传递，从而降低了结合位点保持与其配体分子间结合的能力，从而释放到溶液中。重新质子化将寡聚体的极性恢复到其原始方向，恢复远程结合位点的功能，从而重新捕获配体。这是传递分子间结合信息的合成分子结构的第一个例子，这些“动态折叠”结构是能够从远处控制化学功能的化学系统组件的原型。

  DOI：

  10.1021/jacs.1c11928