fluorescein-4',5'-bis(mercuric trifluoroacetate)

• 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-4',5'-bis(mercuric trifluoroacetate)
• 英文别名: 4',5'-bis(trifluoroacetoxymercuri)fluorescein；[3',6'-Dihydroxy-3-oxo-5'-[(2,2,2-trifluoroacetyl)oxymercurio]spiro[2-benzofuran-1,9'-xanthene]-4'-yl]-(2,2,2-trifluoroacetyl)oxymercury；[3',6'-dihydroxy-3-oxo-5'-[(2,2,2-trifluoroacetyl)oxymercurio]spiro[2-benzofuran-1,9'-xanthene]-4'-yl]-(2,2,2-trifluoroacetyl)oxymercury
• 化学式: C₂₄H₁₀F₆Hg₂O₉
• 分子量: 957.508
• InChiKey: KYKPXIIEBBWLMX-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  0.61
• 重原子数：
  41
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  fluorescein-4',5'-bis(mercuric trifluoroacetate) 、 1,2-乙二硫醇 在 arsenic trichloride 、 palladium diacetate 、 N,N-二异丙基乙胺 作用下， 以 phosphate buffer 、 丙酮 为溶剂， 反应 0.33h， 以34%的产率得到2-[4,5-二(1,3,2-二硫杂砷戊环-2-基)-6-羟基-3-氧代-3H-氧杂蒽-9-基]苯甲酸
  参考文献：
  名称：

  Improved Photostable FRET-Competent Biarsenical−Tetracysteine Probes Based on Fluorinated Fluoresceins

  摘要：

  We have developed fluoro-substituted versions of the biarsenical-tetracysteine label FlAsH, exhibiting significant improvements in important properties over the original fluorescein derivative. In complexes with tetracysteine targets, F2FlAsH exhibits 50 times improved photostability, lower pH sensitivity, higher absorbance and quantum yield than FlAsH, and F4FlAsH adds a new color to the palette of biarsenical dyes. The two probes also provide a new FRET pair with a larger Ro value (54 A) than any previously obtained with biarsenical dyes.

  DOI：

  10.1021/ja063212q

文献信息

• Improved Photostable FRET-Competent Biarsenical−Tetracysteine Probes Based on Fluorinated Fluoresceins
  作者：Carla C. Spagnuolo、Rudolf J. Vermeij、Elizabeth A. Jares-Erijman

  DOI：10.1021/ja063212q

  日期：2006.9.1

  We have developed fluoro-substituted versions of the biarsenical-tetracysteine label FlAsH, exhibiting significant improvements in important properties over the original fluorescein derivative. In complexes with tetracysteine targets, F2FlAsH exhibits 50 times improved photostability, lower pH sensitivity, higher absorbance and quantum yield than FlAsH, and F4FlAsH adds a new color to the palette of biarsenical dyes. The two probes also provide a new FRET pair with a larger Ro value (54 A) than any previously obtained with biarsenical dyes.
• Tetracysteine-tagged prion protein allows discrimination between the native and converted forms
  作者：Jernej Gašperšič、Iva Hafner-Bratkovič、Michel Stephan、Peter Veranič、Mojca Benčina、Ina Vorberg、Roman Jerala

  DOI：10.1111/j.1742-4658.2010.07619.x

  日期：2010.5

  The conformational conversion of prion protein (PrP) from a native conformation to the amyloid form is a hallmark of transmissible spongiform encephalopathies. Conversion is usually monitored by fluorescent dyes, which bind generic amyloids and are less suited for living cell imaging. We report a new method for the synthesis of membrane‐permeable and membrane‐impermeable biarsenical reagents, which are then used to monitor murine PrP (mPrP) misfolding. We introduced tetracysteine (TC) tags into three different positions of mPrP, which folded into a native‐like structure. Whereas mPrPs with a TC tag inserted at the N‐terminus or C‐terminus supported fibril formation, insertion into the helix 2–helix 3 loop inhibited conversion. We devised a quantitative protease‐free method to determine the fraction of converted PrP, based on the ability of the fluorescein arsenical helix binder reagent to differentiate between the monomeric and fibrilized form of TC‐tagged PrP, and showed that TC‐tagged mPrP could be detected on transfected cells, thereby expanding the potential use of this method for the detection and study of conformational diseases.Structured digital abstract MINT‐7709757: Prp (uniprotkb:P04925) and Prp (uniprotkb:P04925) bind (MI:0407) by electron microscopy (MI:0040) MINT‐7709744: Prp (uniprotkb:P04925) and Prp (uniprotkb:P04925) bind (MI:0407) by circular dichroism (MI:0016) MINT‐7709730: Prp (uniprotkb:P04925) and Prp (uniprotkb:P04925) bind (MI:0407) by fluorescence technology (MI:0051)