PF2 | 1224696-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: PF2
• 英文别名: Peroxyfluor-2；3'-Methoxy-6'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one；3'-methoxy-6'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[2-benzofuran-3,9'-xanthene]-1-one
• CAS: 1224696-68-7
• 化学式: C₂₇H₂₅BO₆
• 分子量: 456.303
• InChiKey: WLKNHGFDIDQEJW-UHFFFAOYSA-N

物化性质

• 沸点：
  614.3±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  PF2 在 双氧水 作用下， 以 aq. phosphate buffer 为溶剂， 反应 3.0h， 生成 3-O-methylfluorescein
  参考文献：
  名称：

  过氧化物反应性的硼酸酯偶联的荧光探针：直接接头取代用于检测过氧化物的自消灭接头

  摘要：

  开启荧光探针通常用于有效估计活性氧（例如H 2 O 2）。在本研究中，通过将硼酸酯基团与三种重要的荧光染料直接或通过自消灭性连接剂偶联，合理设计了三套不同的用于检测H 2 O 2的荧光探针。有趣的是，我们的结果表明，在检测痕量外源性和内源性H 2 O 2时，直接连接的硼酸酯探针比含自消灭性接头的探针优越且灵敏。。探针效率的差异还取决于所使用的荧光团单元的性质。考虑到这些方面，我们的详细研究表明，直接连接的基于硼酸酯的荧光素探针19是用于以很高的灵敏度水平有效地检测水性介质和细胞介质中H 2 O 2的最佳探针。在设计用于ROS的荧光传感器以及在与ROS相关的病理学中使用荧光传感器时，本观察结果将是有用的。

  DOI：

  10.1016/j.dyepig.2021.109363
• 作为产物：
  描述：

  6’-methyl-3’-(trifluoromethanesulfonyl)fluorescein 、 联硼酸频那醇酯 在 palladium diacetate 、 N,N-二异丙基乙胺 、 2-(二环己基膦基)联苯 作用下， 以 1,4-二氧六环 为溶剂， 以73%的产率得到PF2
  参考文献：
  名称：

  A Palette of Fluorescent Probes with Varying Emission Colors for Imaging Hydrogen Peroxide Signaling in Living Cells

  摘要：

  We present a new family of fluorescent probes with varying emission colors for selectively imaging hydrogen peroxide (H2O2) generated at physiological cell signaling levels. This structurally homologous series of fluorescein- and rhodol-based reporters relies on a chemospecific boronate-to-phenol switch to respond to H2O2 over a panel of biologically relevant reactive oxygen species (ROS) with tunable excitation and emission maxima and sensitivity to endogenously produced H2O2 signals, as shown by studies in RAW264.7 macrophages during the phagocytic respiratory burst and A431 cells in response to EGF stimulation. We further demonstrate the utility of these reagents in multicolor imaging experiments by using one of the new H2O2-specific probes, Peroxy Orange 1 (PO1), in conjunction with the green-fluorescent highly reactive oxygen species (hROS) probe, APF. This dual-probe approach allows for selective discrimination between changes in H2O2 and hypochlorous acid (HOCl) levels in live RAW264.7 macrophages. Moreover, when macrophages labeled with both PO1 and APF were stimulated to induce an immune response, we discovered three distinct types of phagosomes: those that generated mainly hROS, those that produced mainly H2O2, and those that possessed both types of ROS. The ability to monitor multiple ROS fluxes simultaneously using a palette of different colored fluorescent probes opens new opporunities to disentangle the complex contributions of oxidation biology to living systems by molecular imaging.

  DOI：

  10.1021/ja1014103