dipavaloyl 5-aminofluorescein | 321858-92-8

• 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: dipavaloyl 5-aminofluorescein
• 英文别名: 3-oxo-5-aminospiro-[2-benzofuran-1(3H),9'-[9H]xanthene]-3',6'-diyl bis(2,2-dimethylpropanoate)；Flu-a-Pv；[5-Amino-6'-(2,2-dimethylpropanoyloxy)-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl] 2,2-dimethylpropanoate
• CAS: 321858-92-8
• 化学式: C₃₀H₂₉NO₇
• 分子量: 515.563
• InChiKey: XGJPCOXTGUNRSG-UHFFFAOYSA-N

物化性质

• 沸点：
  681.5±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dipavaloyl 5-aminofluorescein 在 吡啶 、 potassium carbonate 、 caesium carbonate 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 38.0h， 生成 [5-[2-[bis(pyridin-2-ylmethyl)amino]ethyl-(4-nitrophenyl)sulfonylamino]-6'-(2,2-dimethylpropanoyloxy)-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  适用于生物应用的高锌选择性荧光传感器分子

  摘要：

  DOI：

  10.1021/ja002467f
• 作为产物：
  描述：

  三甲基乙酸酐 、 5-氨基荧光素 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 dipavaloyl 5-aminofluorescein
  参考文献：
  名称：

  通过铜（I）催化的叠氮化物-炔烃环加成反应实现6-叠氮基6-脱氧-α-环糊精的协同功能化和部分标记

  摘要：

  在微波和配体辅助的环糊精点击簇合成中，我们观察到在优化的反应条件下6-叠氮基-6-脱氧-α-环糊精的点击反应中的协同过官能化。MALDI-MS数据和通过一锅法/分步法进行的部分荧光素标记证实了协同过官能化的发生：完全由三唑官能化的环糊精点击簇成为炔烃当量受限的主要产品。据我们所知，这项工作是叠氮基-环糊精“合作”点击反应的第一个例子。环糊精点击簇的这种协同功能化为使用叠氮基-环糊精的部分报道分子标记策略提供了有用的综合见解。

  DOI：

  10.1016/j.tetlet.2012.08.080

文献信息

• Design and Synthesis of Highly Sensitive Fluorogenic Substrates for Glutathione S-Transferase and Application for Activity Imaging in Living Cells
  作者：Yuuta Fujikawa、Yasuteru Urano、Toru Komatsu、Kenjiro Hanaoka、Hirotatsu Kojima、Takuya Terai、Hideshi Inoue、Tetsuo Nagano

  DOI：10.1021/ja802423n

  日期：2008.11.5

  Here we report the development of fluorogenic substrates for glutathione S-transferase (GST), a multigene-family enzyme mainly involved in detoxification of endogenous and exogenous compounds, including drug metabolism. GST is often overexpressed in a variety of malignancies and is involved in the development of resistance to various anticancer drugs. Despite the medical significance of this enzyme, no practical fluorogenic substrates for fluorescence imaging of GST activity or for high-throughput screening of GST inhibitors are yet available. So, we set out to develop new fluorogenic substrates for GST. In preliminary studies, we found that 3,4-dinitrobenzanilide (NNBA) is a specific substrate for GST and established the mechanisms of its glutathionylation and denitration. Using these results as a basis for off/on control of fluorescence, we designed and synthesized new fluorogenic substrates, DNAFs, and a cell membrane-permeable variant, DNAT-Me. These fluorogenic substrates provide a dramatic fluorescence increase upon GST-catalyzed glutathionylation and have excellent kinetic parameters for the present purpose. We were able to detect nuclear localization of GSH/GST activity in HuCCT1 cell lines with the use of DNAT-Me. These results indicate that the newly developed fluorogenic substrates should be useful not only for high-throughput GST-inhibitor screening but also for studies on the mechanisms of drug resistance in cancer cells.
• Molecular Tripods Showing Fluorescence Enhancement upon Binding to Streptavidin
  作者：Tae Woo Kim、Hey Young Yoon、Jung-hyun Park、Oh-Hoon Kwon、Du-Jeon Jang、Jong-In Hong

  DOI：10.1021/ol047801h

  日期：2005.1.1

  We introduce a new approach to biotin-streptavidin assays based on a molecular tripod which consists of biotin, a fluorophore, and a quencher. The interaction between streptavidin and molecular tripods perturbs the ground-state quencher-fluorophore dimeric conformation in the absence of streptavidin and diminishes the intrinsic self-quenching of a quencher-fluorophore pair. The emission intensity of the molecular tripods plus streptavidin is 3.5-5.2 times that of molecular tripods in the absence of streptavidin.
• Hishikawa, Kazuhiro; Nakagawa, Hidehiko; Furuta, Toshiaki, Journal of the American Chemical Society, 2009, vol. 131, p. 7488 - 7489
  作者：Hishikawa, Kazuhiro、Nakagawa, Hidehiko、Furuta, Toshiaki、Fukuhara, Kiyoshi、Tsumoto, Hiroki、et al.

  DOI：——

  日期：——
• Quencher–fluorophore ensemble for detection of pyrophosphate in water
  作者：Dong Hoon Lee、Soon Young Kim、Jong-In Hong

  DOI：10.1016/j.tetlet.2007.05.006

  日期：2007.6

  We present a new example of on-off switching using a fluorescent PPi sensor system based on the quencher-fluorophore ensemble, which shows a moderate selectivity for PPi ions among other anions in an aqueous solvent. (c) 2007 Published by Elsevier Ltd.
• USRE40572E1
  申请人：——

  公开号：USRE40572E1

  公开（公告）日：2008-11-11