4',5'-dimethylfluorescein dibenzoate | 357615-01-1

• 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: 4',5'-dimethylfluorescein dibenzoate
• 英文别名: 3',6'-bis-benzoyloxy-4',5'-dimethyl-spiro[phthalan-1,9'-xanthen]-3-one；3',6'-Bis-benzoyloxy-4',5'-dimethyl-spiro[phthalan-1,9'-xanthen]-3-on；(6'-Benzoyloxy-4',5'-dimethyl-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl) benzoate
• CAS: 357615-01-1
• 化学式: C₃₆H₂₄O₇
• 分子量: 568.582
• InChiKey: XWUSLXGQCVNIFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4',5'-dimethylfluorescein dibenzoate 在 1,3-二溴-5,5-二甲基海因 、 碳酸氢钠 、 溶剂黄146 、 二甲基亚砜 、 1,1'-偶氮(氰基环己烷) 作用下， 以 氯苯 为溶剂， 反应 76.0h， 生成 4',5'-fluoresceindicarboxaldehyde
  参考文献：
  名称：

  Fluorescent Sensors for Zn²⁺ Based on a Fluorescein Platform:  Synthesis, Properties and Intracellular Distribution

  摘要：

  Two new fluorescent sensors for Zn2+ that utilize fluorescein as a reporting group, Zinpyr-1 and Zinpyr-2, have been synthesized and characterized. Zinpyr-1 is prepared in one step via a Mannich reaction, and Zinpyr-2 is obtained in a multistep synthesis that utilizes 4 ' ,5 ' -fluorescein dicarboxaldehyde as a key intermediate. Both Zinpyr sensors have excitation and emission wavelengths in the visible range (similar to 500 nm), dissociation constants (K-d1) for Zn2+ of <1 nM, quantum yields approaching unity (Phi = similar to0.9), and cell permeability, making them well-suited for intracellular applications. A 3- to 5-fold fluorescent enhancement is observed under simulated physiological conditions corresponding to the binding of the Zn2+ cation to the sensor, which inhibits a photoinduced electron transfer (PET) quenching pathway. The X-ray crystal structure of a 2:1 Zn2+:Zinpyr-1 complex has also been solved, and is the first structurally characterized example of a complex of fluorescein substituted with metal binding ligands.

  DOI：

  10.1021/ja010059l
• 作为产物：
  描述：

  2,6-二羟基甲苯 在 吡啶 、 zinc(II) chloride 作用下， 反应 2.5h， 生成 4',5'-dimethylfluorescein dibenzoate
  参考文献：
  名称：

  Fluorescent Sensors for Zn²⁺ Based on a Fluorescein Platform:  Synthesis, Properties and Intracellular Distribution

  摘要：

  Two new fluorescent sensors for Zn2+ that utilize fluorescein as a reporting group, Zinpyr-1 and Zinpyr-2, have been synthesized and characterized. Zinpyr-1 is prepared in one step via a Mannich reaction, and Zinpyr-2 is obtained in a multistep synthesis that utilizes 4 ' ,5 ' -fluorescein dicarboxaldehyde as a key intermediate. Both Zinpyr sensors have excitation and emission wavelengths in the visible range (similar to 500 nm), dissociation constants (K-d1) for Zn2+ of <1 nM, quantum yields approaching unity (Phi = similar to0.9), and cell permeability, making them well-suited for intracellular applications. A 3- to 5-fold fluorescent enhancement is observed under simulated physiological conditions corresponding to the binding of the Zn2+ cation to the sensor, which inhibits a photoinduced electron transfer (PET) quenching pathway. The X-ray crystal structure of a 2:1 Zn2+:Zinpyr-1 complex has also been solved, and is the first structurally characterized example of a complex of fluorescein substituted with metal binding ligands.

  DOI：

  10.1021/ja010059l

文献信息

• Fluorescein-based metal sensors, and methods of making and using the same
  申请人：——

  公开号：US20020106697A1

  公开（公告）日：2002-08-08

  The present invention is directed, in part, to fluorescein-based ligands for detection of metal ions, and methods of making and using the same.

  本发明部分涉及用于检测金属离子的荧光素基配体，以及制备和使用它们的方法。
• Sensors, and methods of making and using the same
  申请人：——

  公开号：US20040224420A1

  公开（公告）日：2004-11-11

  The present invention is directed, in part, to sensors for detecting metal ions, and methods of making and using the same.

  本发明部分涉及用于检测金属离子的传感器，以及制备和使用它们的方法。
• Burton; Kurzer, Journal of the Society of Chemical Industry, 1948, vol. 67, p. 345
  作者：Burton、Kurzer

  DOI：——

  日期：——
• US7160732B2
  申请人：——

  公开号：US7160732B2

  公开（公告）日：2007-01-09
• US7399639B2
  申请人：——

  公开号：US7399639B2

  公开（公告）日：2008-07-15