di-tert-butyl 2,2'-((2-(dodecyl(2-(6-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl)amino)ethyl)azanediyl)diacetate | 1610877-96-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: di-tert-butyl 2,2'-((2-(dodecyl(2-(6-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl)amino)ethyl)azanediyl)diacetate
• CAS: 1610877-96-7
• 化学式: C₄₀H₆₀N₄O₈
• 分子量: 724.938
• InChiKey: OVBKOBNLBCEJOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.55
• 重原子数：
  52.0
• 可旋转键数：
  22.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  139.6
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  di-tert-butyl 2,2'-((2-(dodecyl(2-(6-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl)amino)ethyl)azanediyl)diacetate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以71%的产率得到di-tert-butyl 2,2'-((2-((2-(6-amino-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl)(dodecyl)amino)ethyl)azanediyl)diacetate
  参考文献：
  名称：

  Toward a Chemical Marker for Inflammatory Disease: A Fluorescent Probe for Membrane-Localized Thioredoxin

  摘要：

  Thioredoxin (Trx) is a redox-active protein that plays a key role in mitigating the effects of oxidative stress. The secretion of Trx on the plasma membrane has been suggested as a distinctive feature of inflammation. However, selective monitoring of membrane-associated Trx activity has proved challenging because of the ubiquity of Trx action in cells. Here, we report a Trx-specific probe that allows visualization of Trx activity associated with the membranes via fluorescence microscopy. The ability of this probe to act as a possible screening tool for agents that modulate Trx secretion was demonstrated in HeLa cells under oxidative stress conditions and in a cellular hepatosteatosis model. Control experiments serve to confirm that the response seen for the present probe is due to Trx and that it is selective over various potentially competing metabolites, including thiol-containing small molecules and test proteins.

  DOI：

  10.1021/ja503356q
• 作为产物：
  描述：

  在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 di-tert-butyl 2,2'-((2-(dodecyl(2-(6-nitro-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)ethyl)amino)ethyl)azanediyl)diacetate
  参考文献：
  名称：

  Toward a Chemical Marker for Inflammatory Disease: A Fluorescent Probe for Membrane-Localized Thioredoxin

  摘要：

  Thioredoxin (Trx) is a redox-active protein that plays a key role in mitigating the effects of oxidative stress. The secretion of Trx on the plasma membrane has been suggested as a distinctive feature of inflammation. However, selective monitoring of membrane-associated Trx activity has proved challenging because of the ubiquity of Trx action in cells. Here, we report a Trx-specific probe that allows visualization of Trx activity associated with the membranes via fluorescence microscopy. The ability of this probe to act as a possible screening tool for agents that modulate Trx secretion was demonstrated in HeLa cells under oxidative stress conditions and in a cellular hepatosteatosis model. Control experiments serve to confirm that the response seen for the present probe is due to Trx and that it is selective over various potentially competing metabolites, including thiol-containing small molecules and test proteins.

  DOI：

  10.1021/ja503356q