6-hydroxy-9-(4-naphtho-1,8-disulfide)-3H-xanthen-3-one | 935552-39-9

• 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: 6-hydroxy-9-(4-naphtho-1,8-disulfide)-3H-xanthen-3-one
• 英文别名: 9-(2,3-Dithiatricyclo[6.3.1.04,12]dodeca-1(11),4(12),5,7,9-pentaen-7-yl)-6-hydroxyxanthen-3-one；9-(2,3-dithiatricyclo[6.3.1.04,12]dodeca-1(11),4(12),5,7,9-pentaen-7-yl)-6-hydroxyxanthen-3-one
• CAS: 935552-39-9
• 化学式: C₂₃H₁₂O₃S₂
• 分子量: 400.478
• InChiKey: NTJBLDIQXBRQNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-hydroxy-9-(4-naphtho-1,8-disulfide)-3H-xanthen-3-one 在 3,3,3-膦三基三丙酸 作用下， 生成 9-(2,3-dithiatricyclo[6.3.1.04,12]dodeca-1(11),4(12),5,7,9-pentaen-7-yl)-9H-xanthene-3,6-diol
  参考文献：
  名称：

  A Fluorescent Sensor for Imaging Reversible Redox Cycles in Living Cells

  摘要：

  We report the synthesis, properties, and biological applications of Redoxfluor-1 (RF1), a new fluorescent sensor for imaging reversible oxidation-reduction cycles in aqueous solution and in living cells. RF1 is comprised of a fluorescein reporter coupled to a disulfide/dithiol switch. The green fluorescent sensor features a reversible response to multiple oxidation or reduction events, a > 50-fold fluorescence dynamic range, and excitation and emission profiles in the visible region to minimize cellular damage and autofluorescence. Confocal microscopy experiments show that RF1 can visualize multiple cycles of oxidation and reduction within living cells, establishing the potential value of this approach for probing dynamic oxidation biology events in natural systems.

  DOI：

  10.1021/ja0668973
• 作为产物：
  描述：

  9-(2,3-dithiatricyclo[6.3.1.04,12]dodeca-1(11),4(12),5,7,9-pentaen-7-yl)-9H-xanthene-3,6-diol 在 双氧水 作用下， 生成 6-hydroxy-9-(4-naphtho-1,8-disulfide)-3H-xanthen-3-one
  参考文献：
  名称：

  A Fluorescent Sensor for Imaging Reversible Redox Cycles in Living Cells

  摘要：

  We report the synthesis, properties, and biological applications of Redoxfluor-1 (RF1), a new fluorescent sensor for imaging reversible oxidation-reduction cycles in aqueous solution and in living cells. RF1 is comprised of a fluorescein reporter coupled to a disulfide/dithiol switch. The green fluorescent sensor features a reversible response to multiple oxidation or reduction events, a > 50-fold fluorescence dynamic range, and excitation and emission profiles in the visible region to minimize cellular damage and autofluorescence. Confocal microscopy experiments show that RF1 can visualize multiple cycles of oxidation and reduction within living cells, establishing the potential value of this approach for probing dynamic oxidation biology events in natural systems.

  DOI：

  10.1021/ja0668973

文献信息

• A Fluorescent Sensor for Imaging Reversible Redox Cycles in Living Cells
  作者：Evan W. Miller、Shelly X. Bian、Christopher J. Chang

  DOI：10.1021/ja0668973

  日期：2007.3.1

  We report the synthesis, properties, and biological applications of Redoxfluor-1 (RF1), a new fluorescent sensor for imaging reversible oxidation-reduction cycles in aqueous solution and in living cells. RF1 is comprised of a fluorescein reporter coupled to a disulfide/dithiol switch. The green fluorescent sensor features a reversible response to multiple oxidation or reduction events, a > 50-fold fluorescence dynamic range, and excitation and emission profiles in the visible region to minimize cellular damage and autofluorescence. Confocal microscopy experiments show that RF1 can visualize multiple cycles of oxidation and reduction within living cells, establishing the potential value of this approach for probing dynamic oxidation biology events in natural systems.