t-butyl 2-((3'-hydroxy-3-oxo-3H-spiro [isobenzofuran-1,9'-xanthen]-6'-yl)oxy)acetate | 824424-13-7

• 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: t-butyl 2-((3'-hydroxy-3-oxo-3H-spiro [isobenzofuran-1,9'-xanthen]-6'-yl)oxy)acetate
• 英文别名: tert-butyl 2-((3′-hydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthen]-6′-yl)oxy)acetate；Tert-butyl 2-(6'-hydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl)oxyacetate；tert-butyl 2-(6'-hydroxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl)oxyacetate
• CAS: 824424-13-7
• 化学式: C₂₆H₂₂O₇
• 分子量: 446.456
• InChiKey: VGVQSQNPTAZNGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  t-butyl 2-((3'-hydroxy-3-oxo-3H-spiro [isobenzofuran-1,9'-xanthen]-6'-yl)oxy)acetate 在 三乙烯二胺 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 (E)-3′-(2-(tert-butoxy)-2-oxoethoxy)-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthen]-6′-yl 3-(2,6-dimethoxy-4-(3-oxo-1,3,5,6,11,11a-hexahydrooxazolo[3′,4′ :1,6]pyrido[3,4-b]indol-5-yl)phenoxy)acrylate
  参考文献：
  名称：

  抗体引导药物递送至癌细胞的比率荧光监测

  摘要：

  利用来自双染料分子系统的两个独立荧光信号的比率测量有助于提高许多分析、生物分析和药物分析的检测灵敏度和定量，包括药物输送监测。然而，这些双染料偶联物从未用于对抗体 (Ab) 引导的靶向药物递送 (TDD) 进行比例监测。在这里，我们首次报告了新的双染料 TDD 系统 Cy5s-Ab-Flu-Aza，该系统包含与抗癌药物氮杂毒素 (Aza) 连接的可切换荧光素染料 (Flu)，参考五甲川花青染料(Cy5s) 和 Her2 特异性人源化单克隆曲妥珠单抗 (Herceptin) 抗体。该模型系统在体外证明了药物释放的比率荧光监测能力在过表达 Her2 受体的人乳腺癌 SKBR3 细胞系的例子中。用于设计比例、抗体引导 TDD 系统的建议方法，其中“药物可切换染料”偶联物和参考染料独立连接到抗体，可以扩展到其他药物、染料和抗体。用更长波长（红色或近红外）可切换荧光团替代在体内无法检测到的发绿光染料

  DOI：

  10.1021/acs.bioconjchem.1c00205
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 fluorescein disodium salt 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以41.4%的产率得到t-butyl 2-((3'-hydroxy-3-oxo-3H-spiro [isobenzofuran-1,9'-xanthen]-6'-yl)oxy)acetate
  参考文献：
  名称：

  Nucleic Acid-Triggered Fluorescent Probe Activation by the Staudinger Reaction

  摘要：

  Highly sequence specific and sensitive detection systems for DNA or RNA in vivo would be of great use in biology and medicine for monitoring gene expression and diagnosing diseased cells. Herein we describe a new nucleic acid-triggered fluorescent probe system that is activated by a biocompatible and chemoselective Staudinger reaction.

  DOI：

  10.1021/ja0452626

文献信息

• Exploiting fluorescein based drug conjugates for fluorescent monitoring in drug delivery
  作者：Andrii Bazylevich、Leonid D. Patsenker、Gary Gellerman

  DOI：10.1016/j.dyepig.2016.11.057

  日期：2017.4

  Anticancer drugs connected to fluorescein based chemosensors by different biodegradable linkers were investigated for fluorescent monitoring in drug delivery models. The drug release triggered by chemo- and bio-hydrolytic environments was visualized on the basis of "switch on" fluorescence of the fluorophore moiety of fluorescein-drug conjugates. The conjugation of free phenolic hydroxyl of fluorescein chemosensor to the hydroxyl group of the drugs was employed by biodegradable oxy- and amino acrylate linkers. The chemosensor also possesses a free carboxylic group for potential conjugation to a specific carrier for targeted drug delivery applications. Fluorescent monitoring of drug release, quantum yield and other spectroscopic characteristics of our novel fluorescein-drug conjugates were measured and discussed. The work offers a versatile fluorophore platform for the fluorescent observation of drug delivery. (C) 2016 Elsevier Ltd. All rights reserved.
• Dual-dye systems comprising activatable fluorescein dye and hydrophobic or hydrophilic Cy5 reference fluorophore for ratiometric drug delivery monitoring
  作者：Dvir Poplinger、Andrii Bazylevich、Maksym Bokan、Gary Gellerman、Leonid Patsenker

  DOI：10.1016/j.jphotochem.2020.113113

  日期：2021.3
• Nucleic Acid-Triggered Fluorescent Probe Activation by the Staudinger Reaction
  作者：Jianfeng Cai、Xiaoxu Li、Xuan Yue、John Stephen Taylor

  DOI：10.1021/ja0452626

  日期：2004.12.1

  Highly sequence specific and sensitive detection systems for DNA or RNA in vivo would be of great use in biology and medicine for monitoring gene expression and diagnosing diseased cells. Herein we describe a new nucleic acid-triggered fluorescent probe system that is activated by a biocompatible and chemoselective Staudinger reaction.
• Ratiometric Fluorescence Monitoring of Antibody-Guided Drug Delivery to Cancer Cells
  作者：Dvir Poplinger、Maksym Bokan、Arkadi Hesin、Ebaston Thankarajan、Helena Tuchinsky、Gary Gellerman、Leonid Patsenker

  DOI：10.1021/acs.bioconjchem.1c00205

  日期：2021.8.18

  pharmaceutical assays, including drug delivery monitoring. Nevertheless, these dual-dye conjugates have never been utilized for ratiometric monitoring of antibody (Ab)-guided targeted drug delivery (TDD). Here, we report for the first time on the new, dual-dye TDD system, Cy5s-Ab-Flu-Aza, comprising the switchable fluorescein-based dye (Flu) linked to the anticancer drug azatoxin (Aza), reference pentamethine

  利用来自双染料分子系统的两个独立荧光信号的比率测量有助于提高许多分析、生物分析和药物分析的检测灵敏度和定量，包括药物输送监测。然而，这些双染料偶联物从未用于对抗体 (Ab) 引导的靶向药物递送 (TDD) 进行比例监测。在这里，我们首次报告了新的双染料 TDD 系统 Cy5s-Ab-Flu-Aza，该系统包含与抗癌药物氮杂毒素 (Aza) 连接的可切换荧光素染料 (Flu)，参考五甲川花青染料(Cy5s) 和 Her2 特异性人源化单克隆曲妥珠单抗 (Herceptin) 抗体。该模型系统在体外证明了药物释放的比率荧光监测能力在过表达 Her2 受体的人乳腺癌 SKBR3 细胞系的例子中。用于设计比例、抗体引导 TDD 系统的建议方法，其中“药物可切换染料”偶联物和参考染料独立连接到抗体，可以扩展到其他药物、染料和抗体。用更长波长（红色或近红外）可切换荧光团替代在体内无法检测到的发绿光染料