7',19'-Dihydroxy-3-oxospiro[2-benzofuran-1,13'-2-oxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4(9),5,7,10,15,17(22),18,20-decaene]-5-carboxylic acid | 145103-60-2

• 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: 7',19'-Dihydroxy-3-oxospiro[2-benzofuran-1,13'-2-oxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4(9),5,7,10,15,17(22),18,20-decaene]-5-carboxylic acid
• 英文别名: 7',19'-dihydroxy-3-oxospiro[2-benzofuran-1,13'-2-oxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4(9),5,7,10,15,17(22),18,20-decaene]-5-carboxylic acid
• CAS: 145103-60-2
• 化学式: C₂₉H₁₆O₇
• 分子量: 476.442
• InChiKey: YBLABNVFNMZBGY-UHFFFAOYSA-N

物化性质

• 熔点：
  >250°C
• 沸点：
  845.9±65.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)
• 溶解度：
  不溶于水；溶于N,N-二甲基甲酰胺
• 最大波长(λmax)：
  512nm, 598nm

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  36
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7',19'-Dihydroxy-3-oxospiro[2-benzofuran-1,13'-2-oxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4(9),5,7,10,15,17(22),18,20-decaene]-5-carboxylic acid 在 吡啶 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.75h， 生成
  参考文献：
  名称：

  Cell-permeable small molecule probes for site-specific labeling of proteinsElectronic supplementary information (ESI) available: experimental details and characterization of compounds. See http://www.rsc.org/suppdata/cc/b3/b309196a/

  摘要：

  我们已经成功合成了一些用于在活细胞中表达的含N端半胱氨酸蛋白质进行位点特异性标记的小分子探针。它们在纯化蛋白质的体外实验中，以及在活细菌细胞的体内实验中，都成功展示了其进行蛋白质位点特异性共价修饰的效用。

  DOI：

  10.1039/b309196a
• 作为产物：
  描述：

  1,6-二羟基萘 、 偏苯三酸酐 在 甲烷磺酸 作用下， 反应 12.0h， 生成 7',19'-Dihydroxy-3-oxospiro[2-benzofuran-1,13'-2-oxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4(9),5,7,10,15,17(22),18,20-decaene]-5-carboxylic acid
  参考文献：
  名称：

  Cell-permeable small molecule probes for site-specific labeling of proteinsElectronic supplementary information (ESI) available: experimental details and characterization of compounds. See http://www.rsc.org/suppdata/cc/b3/b309196a/

  摘要：

  我们已经成功合成了一些用于在活细胞中表达的含N端半胱氨酸蛋白质进行位点特异性标记的小分子探针。它们在纯化蛋白质的体外实验中，以及在活细菌细胞的体内实验中，都成功展示了其进行蛋白质位点特异性共价修饰的效用。

  DOI：

  10.1039/b309196a

文献信息

• <i>In situ</i> fluorescence imaging reveals that mitochondrial H₂O₂ mediates lysosomal dysfunction in depression
  作者：Xin Wang、Qi Ding、Ying Tian、Wei Wu、Feida Che、Ping Li、Wen Zhang、Wei Zhang、Bo Tang

  DOI：10.1039/d2cc00431c

  日期：——

  We used two novel fluorescent probes for identifying a time-dependent pathological cascade beginning with mitochondrial H₂O₂ accumulation under oxidant stress, which led to elevated lysosomal H₂O₂, and finally resulting in reduced GCase enzymatic activity in the brains of depressed mice.

  我们使用了两种新型荧光探针，以识别从氧化应激下线粒体H₂O₂积累开始的时间依赖性病理级联反应，导致升高的溶酶体H₂O₂，最终导致抑郁小鼠大脑中GCase酶活性降低的结果。
• Cell-permeable small molecule probes for site-specific labeling of proteinsElectronic supplementary information (ESI) available: experimental details and characterization of compounds. See http://www.rsc.org/suppdata/cc/b3/b309196a/
  作者：Dawn S. Y. Yeo、Rajavel Srinivasan、Mahesh Uttamchandani、Grace Y. J. Chen、Qing Zhu、Shao Q. Yao

  DOI：10.1039/b309196a

  日期：——

  We have successfully synthesized a number of small molecule probes designed for site-specific labeling of N-terminal cysteine-containing proteins expressed in live cells. Their utility for site-specific, covalent modifications of proteins was successfully demonstrated with purified proteins in vitro, and with live bacterial cells in vivo.

  我们已经成功合成了一些用于在活细胞中表达的含N端半胱氨酸蛋白质进行位点特异性标记的小分子探针。它们在纯化蛋白质的体外实验中，以及在活细菌细胞的体内实验中，都成功展示了其进行蛋白质位点特异性共价修饰的效用。
• An enhanced fluorescence sensor for specific detection Cys over Hcy/GSH and its bioimaging in living cells
  作者：Tinggui Chen、Xueying Pei、Yongkang Yue、Fangjun Huo、Caixia Yin

  DOI：10.1016/j.saa.2018.10.049

  日期：2019.2

  Cysteine (Cys) is not only the central matter of sulfur metabolism in cells but also the only amino acid with reduced thiol group in 20 kinds of natural amino acids. In animal cells, Cys is taking part in many important and essential biological functions including protein synthesis, detoxification and metabolism. The development and application of fluorescent probes for the detection of Cys have attracted more and more attention and interest. Herein, we report a new fluorescent probe NFA that utilized naphthyl carboxy fluorescein as fluorophore and acryloyl group as reaction site for Cys specific detection. The probe essentially has weak fluorescence. Cys addition to NFA containing system induced distinct enhanced fluorescence emission which was attributed to the nucleophilic reaction of cysteine and acryloyl to release the fluorophore. The signal fluorescent response detection system allows NFA to be a reliable tool for Cys detection with low detection limit (0.58 mu M). And NFA has been successfully applied for Cys imaging specifically in live Hela cells, which promotes the probe as a potential tool to understand the pathology of Cys related diseases. (C) 2018 Elsevier B.V. All rights reserved.