fluorescein bis(2-chloroacetate) | 207568-62-5

• 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: fluorescein bis(2-chloroacetate)
• 英文别名: [6'-(2-Chloroacetyl)oxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl] 2-chloroacetate；[6'-(2-chloroacetyl)oxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl] 2-chloroacetate
• CAS: 207568-62-5
• 化学式: C₂₄H₁₄Cl₂O₇
• 分子量: 485.277
• InChiKey: YCEBDSJPAKLTQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  氯乙酸 、 荧光素 在 四磷十氧化物 作用下， 反应 1.0h， 以92%的产率得到fluorescein bis(2-chloroacetate)
  参考文献：
  名称：

  Synthesis of fluorescein aromatic esters in the presence of P2O5/SiO2 as catalyst and their hydrolysis studies in the presence of lipase

  摘要：

  A series of fluorescein aryl esters were synthesized by the esterification of fluorescein with carboxylic acids in the presence of P2O5/SiO2 and their hydrolytic properties were investigated. The rate of hydrolysis in the presence or absence of lipase, due to the increase of fluorescein concentration, was measured by monitoring of fluorescence of the solution and correlated with enzyme activity. In addition, the substitute effect on the aromatic ring of fluorescein esters was studied. In contrast to fluorescein diacetate or dibutyrate, fluorescein dibenzoate and fluorescein bis(4-methylbenzoate) were found to be better substrates for the fluorometric assay of lipase with the higher rate of hydrolysis and better K-m value, respectively. As little as 9.3 ng mL(-1) of lipase can be detected with fluorescein bis(4-methylbenzoate). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2010.09.013

文献信息

• A Chloroacetate-Caged Fluorescein Chemodosimeter for Imaging Cysteine/Homocysteine in Living Cells
  作者：Baocun Zhu、Yunzhou Zhao、Qi Zhou、Bing Zhang、Lunying Liu、Bin Du、Xiaoling Zhang

  DOI：10.1002/ejoc.201201407

  日期：2013.2

  A chloroacetate-caged fluorescein chemodosimeter (CACFC) employing a double molecular recognition mechanism was designed and synthesized to selectively detect cysteine (Cys) and homocysteine (Hcy) over glutathione (GSH) and other amino acids. The results showed that CACFC could serve as a “naked-eye” indicator, and quantitatively detect Cys and Hcy with a detection limit of 4 μM (Cys) and 7 μM (Hcy)

  设计并合成了一种采用双分子识别机制的氯乙酸酯笼式荧光素化学剂量计 (CACFC)，以选择性检测半胱氨酸 (Cys) 和同型半胱氨酸 (Hcy) 而不是谷胱甘肽 (GSH) 和其他氨基酸。结果表明，CACFC可以作为“肉眼”指标，定量检测Cys和Hcy，检出限分别为4 μM（Cys）和7 μM（Hcy）。此外，CACFC 已成功应用于活细胞中 Cys 和 Hcy 的荧光成像。CACFC 和 Cys/Hcy 之间的反应机制通过 ESI-MS 和荧光光谱分析证实，涉及共轭取代/环化序列。我们强调设计和合成的简单性，并展示其综合特性，例如高特异性、高灵敏度、快速响应、
• Synthesis of fluorescein aromatic esters in the presence of P2O5/SiO2 as catalyst and their hydrolysis studies in the presence of lipase
  作者：Hossein Eshghi、Narges Mirzaie、Ahmad Asoodeh

  DOI：10.1016/j.dyepig.2010.09.013

  日期：2011.5

  A series of fluorescein aryl esters were synthesized by the esterification of fluorescein with carboxylic acids in the presence of P2O5/SiO2 and their hydrolytic properties were investigated. The rate of hydrolysis in the presence or absence of lipase, due to the increase of fluorescein concentration, was measured by monitoring of fluorescence of the solution and correlated with enzyme activity. In addition, the substitute effect on the aromatic ring of fluorescein esters was studied. In contrast to fluorescein diacetate or dibutyrate, fluorescein dibenzoate and fluorescein bis(4-methylbenzoate) were found to be better substrates for the fluorometric assay of lipase with the higher rate of hydrolysis and better K-m value, respectively. As little as 9.3 ng mL(-1) of lipase can be detected with fluorescein bis(4-methylbenzoate). (C) 2010 Elsevier Ltd. All rights reserved.