7a-(6'-hydroxy-4',5'-dimethyl-3'-oxo-3H-xanthen-9'-yl)benzoic acid

• 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: 7a-(6'-hydroxy-4',5'-dimethyl-3'-oxo-3H-xanthen-9'-yl)benzoic acid
• 英文别名: 4',5'-dimethylfluorescein；4,5-dimethylfluorescein；2-(3-Hydroxy-4,5-dimethyl-6-oxoxanthen-9-yl)benzoic acid
• 化学式: C₂₂H₁₆O₅
• 分子量: 360.366
• InChiKey: ZBVXKNUCWXKQIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7a-(6'-hydroxy-4',5'-dimethyl-3'-oxo-3H-xanthen-9'-yl)benzoic acid 在 吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 47.0h， 生成 [6'-[4-[[(4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-propyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]amino]benzoyl]oxy-4',5'-dimethyl-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl] 4-[[(4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-propyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]amino]benzoate
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of a novel class of fluorescein-based N-glycosylamines

  摘要：

  A series of fluorescein-based N-glycosylamines was synthesized from the corresponding fluorescein amine and a partially protected D-glucose. The physiochemical investigation of these compounds by spectral and morphological studies reveals their gelation potential. The exclusive localization of fluorescence in the cytoplasm through cell imaging studies reveals the anti-cancer potentials of N-glycosylamines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.06.001
• 作为产物：
  描述：

  4-氯间苯二酚 在 三氯化铝 、 zinc(II) chloride 作用下， 以 硝基苯 为溶剂， 反应 1.58h， 生成 7a-(6'-hydroxy-4',5'-dimethyl-3'-oxo-3H-xanthen-9'-yl)benzoic acid
  参考文献：
  名称：

  ZP4，一种改进的 Zinpyr 家族神经元 Zn2+传感器

  摘要：

  已合成并表征了 Zinpyr 家族 ZP4 中 Zn(2+) 的第二代荧光传感器。ZP4 (Zinpyr-4, 9-(o-carboxyphenyl)-2-chloro-5-[2-(bis(2-pyridylmethyl)aminomethyl)-N-methylaniline]-6-hydroxy-3-xanthanone)从先前对这些化合物的研究开发的收敛合成策略。ZP4 与其前身一样，在可见光范围内（大约 500 nm）具有激发和发射波长，Zn(2+) 的解离常数 (K(d)) 小于 1 nM 和高量子产率（Phi = 大约0.4），使其非常适合生物应用。在模拟生理条件下观察到 5 倍荧光增强，对应于 Zn(2+) 阳离子与传感器的结合，从而抑制光致电子转移 (PET) 淬火通路。

  DOI：

  10.1021/ja0287377

文献信息

• Synthetic molecules for labeling histidine-rich proteins
  申请人：——

  公开号：US20040143122A1

  公开（公告）日：2004-07-22

  The invention provides Zn-chelating compounds that are molecularly engineered to bind to a specific target sequence in a protein of interest. The Zn 2+ 0 ion is far less toxic and promiscuous than nickel and therefore provides an attractive alternative to Ni-based labeling systems. Invention Zn-chelating compounds also do not require oxidizable thiols and therefore can be used in non-reducing environments such as the surface of living cells. In addition, the target sequence is genetically encodable and requires incorporation of only a few amino acids, unlike fusions to fluorescent proteins such as GFP.

  这项发明提供了分子工程设计的Zn螯合化合物，可以结合到感兴趣蛋白质中的特定靶标序列。Zn2+0离子比镍毒性和广泛性要小得多，因此是镍基标记系统的一个有吸引力的替代选择。该发明的Zn螯合化合物也不需要可氧化的硫醇，因此可以在非还原环境中使用，比如生物细胞表面。此外，靶标序列是遗传可编码的，只需要引入少量氨基酸，不像与荧光蛋白（如GFP）融合那样需要。
• 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.
• US7160732B2
  申请人：——

  公开号：US7160732B2

  公开（公告）日：2007-01-09
• US7465814B2
  申请人：——

  公开号：US7465814B2

  公开（公告）日：2008-12-16
• Design, synthesis, and biological evaluation of a novel class of fluorescein-based N-glycosylamines
  作者：Mani Rajasekar、Sulaiman Mahaboob Khan、Sivasithamparam Niranjali Devaraj、Thangamuthu Mohan Das

  DOI：10.1016/j.carres.2011.06.001

  日期：2011.9

  A series of fluorescein-based N-glycosylamines was synthesized from the corresponding fluorescein amine and a partially protected D-glucose. The physiochemical investigation of these compounds by spectral and morphological studies reveals their gelation potential. The exclusive localization of fluorescence in the cytoplasm through cell imaging studies reveals the anti-cancer potentials of N-glycosylamines. (C) 2011 Elsevier Ltd. All rights reserved.