9-{1-[4-(4-carboxybutyloxy)-2-methylphenyl]}-6-hydroxy-3H-xanthen-3-one | 936030-71-6

• 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: 9-{1-[4-(4-carboxybutyloxy)-2-methylphenyl]}-6-hydroxy-3H-xanthen-3-one
• CAS: 936030-71-6
• 化学式: C₂₅H₂₂O₆
• 分子量: 418.446
• InChiKey: VMCXFLAMPGTGMD-UHFFFAOYSA-N

物化性质

• 沸点：
  725.8±60.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  96.97
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  9-{1-[4-(4-carboxybutyloxy)-2-methylphenyl]}-6-hydroxy-3H-xanthen-3-one 、 溴甲基乙酸酯 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以27%的产率得到9-{1-[4-(4-acetoxymethylcarbonylbutyloxy)-2-methylphenyl]}-6-hydroxy-3H-xanthen-3-one
  参考文献：
  名称：

  An Enzymatically Activated Fluorescence Probe for Targeted Tumor Imaging

  摘要：

  beta-Galactosidase is a widely used reporter enzyme, but although several substrates are available for in vitro detection, its application for in vivo optical imaging remains a challenge. To obtain a probe suitable for in vivo use, we modified our previously developed activatable fluorescence probe, TG-beta Gal (J. Am. Chem. Soc. 2005, 127, 4888-4894), on the basis of photochemical and photophysical experiments. The new probe, AM-TG-beta Gal, provides a dramatic fluorescence enhancement upon reaction with beta-galactosidase, and further hydrolysis of the ester moiety by ubiquitous intracellular esterases affords a hydrophilic product that is well retained within the cells without loss of fluorescence. We used a mouse tumor model to assess the practical utility of AM-TG-beta Gal, after confirming that tumors in the model could be labeled with an avidin-beta-galactosidase conjugate. This conjugate was administered to the mice in vivo, followed by AM-TG-beta Gal, and subsequent ex vivo fluorescence imaging clearly visualized intraperitoneal tumors as small as 200 mu m. This strategy has potential clinical application, for example, in video-assisted laparoscopic tumor resection.

  DOI：

  10.1021/ja067710a
• 作为产物：
  描述：

  9-{1-[4-(tert-butyldimethylsilyloxy)-2-methylphenyl]}-6-hydroxy-3H-xanthen-3-one 在 sodium hydroxide 、 四丁基氟化铵 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 9-{1-[4-(4-carboxybutyloxy)-2-methylphenyl]}-6-hydroxy-3H-xanthen-3-one
  参考文献：
  名称：

  An Enzymatically Activated Fluorescence Probe for Targeted Tumor Imaging

  摘要：

  beta-Galactosidase is a widely used reporter enzyme, but although several substrates are available for in vitro detection, its application for in vivo optical imaging remains a challenge. To obtain a probe suitable for in vivo use, we modified our previously developed activatable fluorescence probe, TG-beta Gal (J. Am. Chem. Soc. 2005, 127, 4888-4894), on the basis of photochemical and photophysical experiments. The new probe, AM-TG-beta Gal, provides a dramatic fluorescence enhancement upon reaction with beta-galactosidase, and further hydrolysis of the ester moiety by ubiquitous intracellular esterases affords a hydrophilic product that is well retained within the cells without loss of fluorescence. We used a mouse tumor model to assess the practical utility of AM-TG-beta Gal, after confirming that tumors in the model could be labeled with an avidin-beta-galactosidase conjugate. This conjugate was administered to the mice in vivo, followed by AM-TG-beta Gal, and subsequent ex vivo fluorescence imaging clearly visualized intraperitoneal tumors as small as 200 mu m. This strategy has potential clinical application, for example, in video-assisted laparoscopic tumor resection.

  DOI：

  10.1021/ja067710a