5-carboxy-2',7'-dichlorofluorescein diacetate

• 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: 5-carboxy-2',7'-dichlorofluorescein diacetate
• 英文别名: 5-(and 6-)-Carboxy-2',7'-dichlorofluorescein diacetate；5-Carboxy-2',7'-dichlorofluorescein DA；3',6'-diacetyloxy-2',7'-dichloro-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxylic acid
• 化学式: C₂₅H₁₄Cl₂O₉
• mdl: MFCD00037454
• 分子量: 529.287
• InChiKey: AJIVVDSJIOOZOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-carboxy-2',7'-dichlorofluorescein diacetate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以85%的产率得到2,4-dicarboxy-5'-chloro-2',4'-dihydroxybenzophenone
  参考文献：
  名称：

  异构纯的羧酸根和磺酸根取代的x吨荧光团的合成

  摘要：

  基于吨的荧光团，例如荧光素和若丹明，通常通过适当的间苯二酚或3-氨基苯酚与邻苯二甲酸酐的酸催化缩合而制备。取代的邻苯二甲酸酐物质的缩合导致官能化的荧光团形成为混合异构体。在别处已经报道了用于对称荧光素羧酸盐的用于异构体分离的结晶方法。我们描述了基于结晶的受保护的荧光素磺酸盐的分离和偶联条件，以形成磺酰胺，羧酸取代的若丹明的前体，以及不对称取代的荧光素和Rhodafluors的前体。

  DOI：

  10.1016/j.tet.2005.01.024

文献信息

• Fluorescent Fiber-Optic Calcium Sensor for Physiological Measurements
  作者：Michael Shortreed、Raoul Kopelman、Michael Kuhn、Brian Hoyland

  DOI：10.1021/ac950944k

  日期：1996.1.1

  A new optical sensor based on covalent immobilization of a newly synthesized calcium-selective, long-wavelength, fluorescent indicator has been constructed, with a response dynamic range optimal for physiological measurements. Immobilization occurs via photoinitiated copolymerization of the indicator with acrylamide on the distal end of a silanized 125 μm diameter multimode optical fiber. The working lifetime of this sensor is limited only by photobleaching of the indicator. Due to the inherent hydrophilic nature of the acrylamide polymer, the response time of this new sensor is governed by simple aqueous diffusion of the ionic calcium. This results in sensor response times fast enough to monitor some concentration fluctuations at physiological rates. The ability to monitor calcium concentration fluctuations in a high background level of magnesium is also demonstrated with a calculated selectivity of 10-4.5.

  一种新型光学传感器是基于共价固定新合成的钙选择性长波长荧光指示剂而构建的，其响应动态范围最适合生理测量。在直径为 125 μm 的硅烷化多模光纤远端，指示剂与丙烯酰胺通过光引发共聚发生固定。这种传感器的工作寿命仅受指示剂光漂白的限制。由于丙烯酰胺聚合物固有的亲水性，这种新型传感器的响应时间受离子钙的简单水扩散控制。这使得传感器的响应时间足够快，可以监测到一些生理速率的浓度波动。在镁的高背景水平下监测钙浓度波动的能力也得到了证实，计算出的选择性为 10-4.5。
• Taggable fluorescent probe for calcium ion detection
  申请人：The University of Tokyo

  公开号：US10884004B2

  公开（公告）日：2021-01-05

  A fluorescent probe for calcium ion detection that has an excellent photofading resistance and quick Ca2+ detection kinetics and can be localized at an arbitrary site in a cell is provided. The fluorescent probe contains a compound represented by the following general formula (I) or a salt thereof: A method for detecting intracellular calcium ions including (a) introducing the compound above or a salt thereof into a cell and (b) measuring the fluorescence emitted by the compound or a salt thereof in the cell is also provided.

  本发明提供了一种用于检测钙离子的荧光探针，该探针具有优异的抗光褪色性和快速的 Ca2+ 检测动力学特性，并可定位于细胞中的任意部位。该荧光探针含有由以下通式（I）代表的化合物或其盐： 还提供了一种检测细胞内钙离子的方法，包括(a)将上述化合物或其盐引入细胞，(b)测量该化合物或其盐在细胞内发出的荧光。
• TAGGABLE FLUORESCENT PROBE FOR CALCIUM ION DETECTION
  申请人：THE UNIVERSITY OF TOKYO

  公开号：US20190094248A1

  公开（公告）日：2019-03-28

  A fluorescent probe for calcium ion detection that has an excellent photofading resistance and quick Ca 2+ detection kinetics and can be localized at an arbitrary site in a cell is provided. The fluorescent probe contains a compound represented by the following general formula (I) or a salt thereof: A method for detecting intracellular calcium ions including (a) introducing the compound above or a salt thereof into a cell and (b) measuring the fluorescence emitted by the compound or a salt thereof in the cell is also provided.
• NOVEL FLUORESCENT LABELING METHOD
  申请人：The University of Tokyo

  公开号：US20200199174A1

  公开（公告）日：2020-06-25

  A method for fluorescently labeling an intracellular protein through use of a fluorescence ON/OFF control technique includes intracellularly obtaining a fusion protein of a protein to be labeled and an anti-DNP antibody, bringing a compound represented by or its salt into contact with the cell, and fluorescently labeling the protein to be labeled by reacting the fusion protein and the compound or its salt.
• [EN] NOVEL FLUORESCENT LABELING METHOD<br/>[FR] NOUVEAU PROCÉDÉ DE MARQUAGE FLUORESCENT<br/>[JA] 新規蛍光標識方法
  申请人：UNIV TOKYO

  公开号：WO2018135598A1

  公开（公告）日：2018-07-26

  【解決課題】　蛍光ＯＮ／ＯＦＦの制御技術を用いた新規な細胞内タンパク質の蛍光標識の方法を提供すること。 【解決手段】　細胞内タンパク質を蛍光標識する方法であって、標識対象タンパク質と抗ＤＮＰ抗体の融合タンパク質を細胞内で得ること、式（Ｉ）で表される化合物又はその塩を前記細胞と接触させること、及び前記融合タンパク質と式（Ｉ）で表される化合物又はその塩とを反応させることにより、前記対象タンパク質を蛍光標識することを含む、タンパク質を蛍光標識する方法。