3,4,5,6-tetrafluorofluorescein

• 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: 3,4,5,6-tetrafluorofluorescein
• 英文别名: 2,3,4,5-Tetrafluoro-6-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• 化学式: C₂₀H₈F₄O₅
• 分子量: 404.274
• InChiKey: QKWFGQFONYVTMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,4,5,6-tetrafluorofluorescein 在 吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 di-tert-butyl (4,5,6,7-tetrafluoro-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl)dicarbamate
  参考文献：
  名称：

  RED-SHIFTED FLUOROPHORES

  摘要：

  提供了以下结构的化合物：

  公开号：

  US20210171490A1
• 作为产物：
  描述：

  在 聚甘氨酸 、 magnesium chloride 、 zinc(II) chloride 、 alkaline phosphatase 作用下， 反应 1.0h， 生成 3,4,5,6-tetrafluorofluorescein
  参考文献：
  名称：

  Novel fluorogenic substrates for acid phosphatase

  摘要：

  Fluorinated versions of fluorescein diphosphate (FDP) can provide significantly enhanced fluorescence upon hydrolysis by acid phosphatase, as compared with FDP, when measured at the reaction pH. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00199-7

文献信息

• Probing the target-specific inhibition of sensitized protein tyrosine phosphatases with biarsenical probes
  作者：Adam Pomorski、Justyna Adamczyk、Anthony C. Bishop、Artur Krężel

  DOI：10.1039/c4ob02256d

  日期：——

  Selective control of enzyme activity is critical for elucidating the roles of specific proteins in signaling pathways. One potential means for developing truly target-specific inhibitors involves the use of protein engineering to sensitize a target enzyme to inhibition by a small molecule that does not inhibit homologous wild-type enzymes. Previously, it has been shown that protein tyrosine phosphatases

  酶活性的选择性控制对于阐明特定蛋白在信号通路中的作用至关重要。开发真正的靶标特异性抑制剂的一种潜在手段包括使用蛋白质工程技术使靶标酶对不抑制同源野生型酶的小分子产生抑制作用。以前，已经显示蛋白质酪氨酸磷酸酶（PTP）可以被双砷探针FlAsH-EDT 2抑制。，通过与已引入催化重要区域的半胱氨酸残基特异性结合来抑制PTP活性。在本研究中，我们开发了一系列双砷探针，其中一些是新合成的，一些先前已报道过，以首次研究双砷抑制PTP的构效关系。我们的数据表明，在2'和7'位置含有取代的双砷探针在抑制致敏PTP方面比FlAsH-EDT 2更有效。当同时使用两种对位试剂测定PTP时，观察到2'，7'-取代探针的效力增加-硝基苯基磷酸酯和磷酸肽PTP底物，并且处于多个探针浓度。数据进一步表明，增强的抑制特性是2'，7'-取代的双砷探针与致敏PTP之间结合亲和力提高的结果。此外，我们为各种双砷探针提供了以前未知的理化和稳定性数据。
• Novel derivatization of protein thiols with fluorinated fluoresceins
  作者：Kyle R. Gee、Wei-Chuan Sun、Dieter H. Klaubert、Richard P. Haugland、Rosalyn H. Upson、Thomas H. Steinberg、Martin Poot

  DOI：10.1016/0040-4039(96)01794-7

  日期：1996.10

  Fluorescein diacetate analogs 3a–3c are shown to react selectively with protein sulfhydryl groups at neutral pH in aqueous solution, by means of substitution at the perfluorinated ring. The acetate moieties are cleaved by treatment with aqueous carbonate or by endogenous esterases, giving a fluorescent protein conjugate.

  荧光素二乙酸酯类似物3a-3c通过在全氟环上的取代，在水溶液中性pH下与蛋白质巯基选择性反应。通过用碳酸盐水溶液或通过内源酯酶处理来切割乙酸酯部分，得到荧光蛋白缀合物。
• 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.
• Synthesis of Fluorinated Fluoresceins
  作者：Wei-Chuan Sun、Kyle R. Gee、Dieter H. Klaubert、Richard P. Haugland

  DOI：10.1021/jo9706178

  日期：1997.9.1

  Several novel fluorinated fluoresceins (Oregon Green dyes) were prepared by the reaction of fluororesorcinols with phthalic anhydride and its derivatives. A novel regiospecific synthesis of fluororesorcinols was key to the successful synthesis of these new fluorophores. (Polyfluoro)-nitrobenzenes were reacted with 2 equiv of sodium methoxide followed by reduction, hydrodediazoniation, and demethylation, giving the first straightforward synthesis of 2-fluororesorcinol, 4-fluororesorcinol, 2,4-difluororesorcinol, and 2,4,5-trifluororesorcinol. These fluorinated fluoresceins have higher photostability and ionize at a lower pH (pK(a) = 3.3-6.1) than fluorescein (pK(a) = 6.5). Some of the fluorinated fluoresceins have very high quantum yields (0.85-0.97), which, in combination with their lower pK(a)s and high photostability, makes them superior fluorescent dyes for use as reporter molecules in biological systems.
• Rose Bengal analogs and vesicular glutamate transporters (VGLUTs)
  作者：Nicolas Pietrancosta、Albane Kessler、Franck-Cyril Favre-Besse、Nicolas Triballeau、Thomas Quentin、Bruno Giros、Salah El Mestikawy、Francine C. Acher

  DOI：10.1016/j.bmc.2010.06.069

  日期：2010.9

  Vesicular glutamate transporters (VGLUTs) allow the loading of presynaptic glutamate vesicles and thus play a critical role in glutamatergic synaptic transmission. Rose Bengal (RB) is the most potent known VGLUT inhibitor (K-i 25 nM); therefore we designed, synthesized and tested in brain preparations, a series of analogs based on this scaffold. We showed that among the two tautomers of RB, the carboxylic and not the lactonic form is active against VGLUTs and generated a pharmacophore model to determine the minimal structure requirements. We also tested RB specificity in other neurotransmitter uptake systems. RB proved to potently inhibit VMAT (K-i 64 nM) but weakly VACHT (K-i > 9.7 mu M) and may be a useful tool in glutamate/acetylcholine co-transmission studies. (C) 2010 Elsevier Ltd. All rights reserved.