4',5'-bis(bromomethyl)fluoresceine dibenzoate | 357615-02-2

• 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'-bis(bromomethyl)fluoresceine dibenzoate
• 英文别名: [6'-Benzoyloxy-4',5'-bis(bromomethyl)-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl] benzoate
• CAS: 357615-02-2
• 化学式: C₃₆H₂₂Br₂O₇
• 分子量: 726.374
• InChiKey: WFRYVNBZYHFQSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  45
• 可旋转键数：
  8
• 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'-bis(bromomethyl)fluoresceine dibenzoate 在 碳酸氢钠 、 二甲基亚砜 作用下， 反应 4.0h， 以36.7%的产率得到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 、 1,3-二溴-5,5-二甲基海因 、 溶剂黄146 、 zinc(II) chloride 、 1,1'-偶氮(氰基环己烷) 作用下， 以 氯苯 为溶剂， 反应 74.5h， 生成 4',5'-bis(bromomethyl)fluoresceine 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。
• Templated alkylation of hexahistidine with Baylis–Hillman esters
  作者：Xing Xin Liu、Artem Melman

  DOI：10.1039/c3cc43271h

  日期：——

  Alkylation of one of the imidazole rings of hexahistidine with Baylis–Hillman esters tethered to nitrilotriacetate residue was achieved in aqueous solutions at neutral pH and at micromolar concentrations in the presence of Ni2+, Cu2+, or Zn2+ cations. The utility of the approach for selective functionalization of His-tagged recombinant proteins was demonstrated by attachment of a fluorescent label to recombinant protein A with an alkynyl group followed by a “click” 1,3-dipolar cycloaddition reaction.

  在Ni2+、Cu2+或Zn2+阳离子存在下，在pH值为中性、浓度为微摩尔的水溶液中，实现了六组苷的一个咪唑环与连接到硝基三乙酸残基的BaylisâHillman酯的烷基化。通过 "click "1,3-二极环加成反应将荧光标签连接到带有炔基的重组蛋白A上，证明了这种方法在选择性地对His标记的重组蛋白进行功能化方面的实用性。
• Method for selective derivatization of oligohistidine sequence of recombinant proteins
  申请人：Melman Artem

  公开号：US09441010B2

  公开（公告）日：2016-09-13

  Methods and compositions for the selective derivatization of a oligohistidine-tagged recombinant protein. A modifying compound comprised of an imidazole reactive group, a linker, and a ligating group is contacted with the recombinant protein, and a cooperative bond forms between the ligating group and the oligohistidine tag in the presence of a metal cation, and a covalent bond forms between the imidazole reactive group and an imidazole ring of the oligohistidine tag followed by the concomitant separation of the imidazole reactive group from the linker. Addition of a metal chelator results in the dissociation of the ligating group and the oligohistidine tag.

  本发明涉及一种选择性衍生化寡组氨酸标记的重组蛋白的方法和组合物。该改性化合物包含咪唑反应基团、连接剂和配基基团，与重组蛋白接触时，在金属阳离子存在下，配基基团与寡组氨酸标记之间形成协同键，并且咪唑反应基团与寡组氨酸标记中的咪唑环之间形成共价键，随后咪唑反应基团与连接剂分离。添加金属螯合剂可导致配基基团与寡组氨酸标记的解离。
• 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。
• Studies on the synthesis and the antimicrobial and antioxidant activities of a novel class of fluorescein-based glycosides
  作者：Mani Rajasekar、Raman Jegadeesh、Nanjian Raaman、Thangamuthu Mohan Das

  DOI：10.1016/j.carres.2011.08.005

  日期：2011.11

  Facile glycosylation of a fluorescein diol derivative with per-O-acetylibenzoyl sugar derivatives using BF3 center dot Et2O catalyst resulted in the formation of the expected glycosides in 54-66% yield. The biological screening of the glycosides against different microbes shows good inhibitory activity. The antioxidant activity of the fluorescein-based glycosides shows remarkable inhibition (IC50 similar to 80%). (C) 2011 Elsevier Ltd. All rights reserved.