1-((1H-imidazol-1-yl)methyl)-3-(pyren-1-ylmethyl)-1H-imidazol-3-ium bromide | 1189512-75-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1-((1H-imidazol-1-yl)methyl)-3-(pyren-1-ylmethyl)-1H-imidazol-3-ium bromide
• CAS: 1189512-75-1
• 化学式: Br*C₂₄H₁₉N₄
• 分子量: 443.346
• InChiKey: DRELYIXQWOLBKM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.63
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,4-二(溴甲基)苯 、 1-((1H-imidazol-1-yl)methyl)-3-(pyren-1-ylmethyl)-1H-imidazol-3-ium bromide 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Unique Sandwich Stacking of Pyrene-Adenine-Pyrene for Selective and Ratiometric Fluorescent Sensing of ATP at Physiological pH

  摘要：

  A pincer-like benzene-bridged sensor 1 with a pyrene excimer as a signal source and imidazolium as a phosphate anion receptor was synthesized and investigated for ATP sensing. A unique switch of excimer vs monomer pyrene fluorescence of 1 is observed in the presence of ATP due to the charcteristic sandwich pi-pi stacking of pyrene-adenine-pyrene. On the other hand, four other bases of nucleoside triphosphates such as,GTP, CTP, UTP, and TTP can interact only from the outside with the already stabilized stacked pyrene-pyrene dimer of 1, resulting in excimer fluorescence quenching. The fluorescent intensity ratio of monomer-to-excimer for 1 upon binding with ATP (I-375/I-487) is much larger than that upon binding with ADP and AMP. This difference is large enough to discriminate ATP from ADP and AMP. As one of the biological applications, sensor 1 is successfully applied to the ATP staining experiments. Sensor 1 is also applied to monitor the hydrolysis of ATP and ADP by apyrase. The results indicate that I is a useful fluorescent sensor for investigations of ATP-relevant biological processes.

  DOI：

  10.1021/ja906855a
• 作为产物：
  描述：

  N,N-二咪唑基甲烷 、 1-(溴甲基)芘 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 1-((1H-imidazol-1-yl)methyl)-3-(pyren-1-ylmethyl)-1H-imidazol-3-ium bromide
  参考文献：
  名称：

  Unique Sandwich Stacking of Pyrene-Adenine-Pyrene for Selective and Ratiometric Fluorescent Sensing of ATP at Physiological pH

  摘要：

  A pincer-like benzene-bridged sensor 1 with a pyrene excimer as a signal source and imidazolium as a phosphate anion receptor was synthesized and investigated for ATP sensing. A unique switch of excimer vs monomer pyrene fluorescence of 1 is observed in the presence of ATP due to the charcteristic sandwich pi-pi stacking of pyrene-adenine-pyrene. On the other hand, four other bases of nucleoside triphosphates such as,GTP, CTP, UTP, and TTP can interact only from the outside with the already stabilized stacked pyrene-pyrene dimer of 1, resulting in excimer fluorescence quenching. The fluorescent intensity ratio of monomer-to-excimer for 1 upon binding with ATP (I-375/I-487) is much larger than that upon binding with ADP and AMP. This difference is large enough to discriminate ATP from ADP and AMP. As one of the biological applications, sensor 1 is successfully applied to the ATP staining experiments. Sensor 1 is also applied to monitor the hydrolysis of ATP and ADP by apyrase. The results indicate that I is a useful fluorescent sensor for investigations of ATP-relevant biological processes.

  DOI：

  10.1021/ja906855a