4-chloro-7-nitrobenzofurazan | 31079-21-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-chloro-7-nitrobenzofurazan
• 英文别名: NBD-Cl；4-Chlor-7-nitrobenzofurazan；4-chloro-7-nitro-1,3-dihydro-2,1,3-benzoxadiazole
• CAS: 31079-21-7
• 化学式: C₆H₄ClN₃O₃
• 分子量: 201.569
• InChiKey: KAAWUNNATGYOOB-UHFFFAOYSA-N

物化性质

• 沸点：
  319.2±52.0 °C(Predicted)
• 密度：
  1.607±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-chloro-7-nitrobenzofurazan 、 6-巯基己-1-醇 生成 NBDHEX
  参考文献：
  名称：

  Design and Synthesis of Highly Sensitive Fluorogenic Substrates for Glutathione S-Transferase and Application for Activity Imaging in Living Cells

  摘要：

  Here we report the development of fluorogenic substrates for glutathione S-transferase (GST), a multigene-family enzyme mainly involved in detoxification of endogenous and exogenous compounds, including drug metabolism. GST is often overexpressed in a variety of malignancies and is involved in the development of resistance to various anticancer drugs. Despite the medical significance of this enzyme, no practical fluorogenic substrates for fluorescence imaging of GST activity or for high-throughput screening of GST inhibitors are yet available. So, we set out to develop new fluorogenic substrates for GST. In preliminary studies, we found that 3,4-dinitrobenzanilide (NNBA) is a specific substrate for GST and established the mechanisms of its glutathionylation and denitration. Using these results as a basis for off/on control of fluorescence, we designed and synthesized new fluorogenic substrates, DNAFs, and a cell membrane-permeable variant, DNAT-Me. These fluorogenic substrates provide a dramatic fluorescence increase upon GST-catalyzed glutathionylation and have excellent kinetic parameters for the present purpose. We were able to detect nuclear localization of GSH/GST activity in HuCCT1 cell lines with the use of DNAT-Me. These results indicate that the newly developed fluorogenic substrates should be useful not only for high-throughput GST-inhibitor screening but also for studies on the mechanisms of drug resistance in cancer cells.

  DOI：

  10.1021/ja802423n

文献信息

• SEPANIAK, MICHAEL J.;SWAILE, DAVID F.;POWELL, A. CRAIG;COLE, RODERIC O., J. HIGH RESOLUT. CHROMATOGR., 13,(1990) N0, C. 679-682
  作者：SEPANIAK, MICHAEL J.、SWAILE, DAVID F.、POWELL, A. CRAIG、COLE, RODERIC O.

  DOI：——

  日期：——
• Cellular Uptake of a Fluorescent Calix[4]arene Derivative
  作者：Ruth Lalor、Hugo Baillie-Johnson、Carl Redshaw、Susan E. Matthews、Anja Mueller

  DOI：10.1021/ja0782596

  日期：2008.3.1

  A rapid synthetic route to a nontoxic fluorescently labeled water-soluble calixarene has been developed. Investigation of the cellular uptake of the labeled calixarene, via confocal microscopy, through coincubation with uptake inhibitors demonstrates that uptake is not through the common clathrin coated pits or caveolae (lipid raft) endocytic pathways and that the calixarene derivative localizes within the cytoplasm and does not enter the nucleus. The study demonstrates the power of fluorescent labeling for investigation of interactions between calixarenes and biological systems and the potential for calixarene based intracellular imaging agents.