2-(10-hydroxy-11-(((2-methylquinolin-8-yl)amino)methyl)-3-oxo-3H-benzo[c]xanthen-7-yl)benzoic acid | 1333432-87-3

• 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: 2-(10-hydroxy-11-(((2-methylquinolin-8-yl)amino)methyl)-3-oxo-3H-benzo[c]xanthen-7-yl)benzoic acid
• 英文别名: 2-[10-Hydroxy-11-[[(2-methylquinolin-8-yl)amino]methyl]-3-oxobenzo[c]xanthen-7-yl]benzoic acid；2-[10-hydroxy-11-[[(2-methylquinolin-8-yl)amino]methyl]-3-oxobenzo[c]xanthen-7-yl]benzoic acid
• CAS: 1333432-87-3
• 化学式: C₃₅H₂₄N₂O₅
• 分子量: 552.586
• InChiKey: LDBLIDMNXJGBTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  42
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 三乙酰氧基硼氢化钠 、 碳酸氢钠 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-(10-hydroxy-11-(((2-methylquinolin-8-yl)amino)methyl)-3-oxo-3H-benzo[c]xanthen-7-yl)benzoic acid
  参考文献：
  名称：

  Seminaphthofluorescein-Based Fluorescent Probes for Imaging Nitric Oxide in Live Cells

  摘要：

  Fluorescent turn-on probes for nitric oxide based on seminaphthofluorescein scaffolds were prepared and spectroscopically characterized. The Cu(II) complexes of these fluorescent probes react with NO under anaerobic conditions to yield a 20-45-fold increase in integrated emission. The seminaphthofluorescein-based probes emit at longer wavelengths than the parent FL1 and FL2 fluorescein-based generations of NO probes, maintaining emission maxima between 550 and 625 nm. The emission profiles depend on the excitation wavelength; maximum fluorescence turn-on is achieved at excitations between 535 and 575 nm. The probes are highly selective for NO over other biologically relevant reactive nitrogen and oxygen species including NO3-, NO2-, HNO, ONOO-, NO2, OCl-, and H2O2. The seminaphthofluorescein-based probes can be used to visualize endogenously produced NO in live cells, as demonstrated using Raw 264.7 macrophages.

  DOI：

  10.1021/ic200986v

文献信息

• Seminaphthofluorescein-Based Fluorescent Probes for Imaging Nitric Oxide in Live Cells
  作者：Michael D. Pluth、Maria R. Chan、Lindsey E. McQuade、Stephen J. Lippard

  DOI：10.1021/ic200986v

  日期：2011.10.3

  Fluorescent turn-on probes for nitric oxide based on seminaphthofluorescein scaffolds were prepared and spectroscopically characterized. The Cu(II) complexes of these fluorescent probes react with NO under anaerobic conditions to yield a 20-45-fold increase in integrated emission. The seminaphthofluorescein-based probes emit at longer wavelengths than the parent FL1 and FL2 fluorescein-based generations of NO probes, maintaining emission maxima between 550 and 625 nm. The emission profiles depend on the excitation wavelength; maximum fluorescence turn-on is achieved at excitations between 535 and 575 nm. The probes are highly selective for NO over other biologically relevant reactive nitrogen and oxygen species including NO3-, NO2-, HNO, ONOO-, NO2, OCl-, and H2O2. The seminaphthofluorescein-based probes can be used to visualize endogenously produced NO in live cells, as demonstrated using Raw 264.7 macrophages.