4,6-difluoro-1,2,3,3-tetramethylindolenium iodide | 1211408-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4,6-difluoro-1,2,3,3-tetramethylindolenium iodide
• CAS: 1211408-59-1
• 化学式: C₁₂H₁₄F₂N*I
• 分子量: 337.151
• InChiKey: CZAVVSRSNPRGCN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.01
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  3.01
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  N-phenyl-N-(3-phenyliminoprop-1-enyl)acetamide 、 4,6-difluoro-1,2,3,3-tetramethylindolenium iodide 在 sodium acetate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以40 mg的产率得到4,4',6,6'-tetrafluoro-1,1',3,3,3',3'-hexamethylindodicarbocyanine iodide
  参考文献：
  名称：

  Development and Application of a Near-Infrared Fluorescence Probe for Oxidative Stress Based on Differential Reactivity of Linked Cyanine Dyes

  摘要：

  Reactive oxygen species (ROS) operate as signaling molecules under various physiological conditions, and overproduction of ROS is involved in the pathogenesis of many diseases. Therefore, fluorescent probes for visualizing ROS are promising tools with which to uncover the molecular mechanisms of physiological and pathological processes and might also be useful for diagnosis. Here we describe a novel fluorescence probe, FOSCY-1, operating in the physiologically favorable near-infrared region. The probe consists of two differentially ROS-reactive cyanine dyes connected by a linker; reaction of the more susceptible dye with ROS releases intramolecular fluorescence quenching of the less susceptible dye. We successfully applied this probe to detect ROS produced by HL60 cells and porcine neutrophils and for imaging oxidative stress in a mouse model of peritonitis.

  DOI：

  10.1021/ja910090v
• 作为产物：
  描述：

  4,6-difluoro-2,3,3-trimethylindolenine 、 碘甲烷 反应 12.0h， 以66%的产率得到4,6-difluoro-1,2,3,3-tetramethylindolenium iodide
  参考文献：
  名称：

  Development and Application of a Near-Infrared Fluorescence Probe for Oxidative Stress Based on Differential Reactivity of Linked Cyanine Dyes

  摘要：

  Reactive oxygen species (ROS) operate as signaling molecules under various physiological conditions, and overproduction of ROS is involved in the pathogenesis of many diseases. Therefore, fluorescent probes for visualizing ROS are promising tools with which to uncover the molecular mechanisms of physiological and pathological processes and might also be useful for diagnosis. Here we describe a novel fluorescence probe, FOSCY-1, operating in the physiologically favorable near-infrared region. The probe consists of two differentially ROS-reactive cyanine dyes connected by a linker; reaction of the more susceptible dye with ROS releases intramolecular fluorescence quenching of the less susceptible dye. We successfully applied this probe to detect ROS produced by HL60 cells and porcine neutrophils and for imaging oxidative stress in a mouse model of peritonitis.

  DOI：

  10.1021/ja910090v