9-[1-(2-methoxy-4-methoxycarbonylmethoxyphenyl)]-3H-xanthen-3-on-6-yl-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranoside) | 936030-66-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-[1-(2-methoxy-4-methoxycarbonylmethoxyphenyl)]-3H-xanthen-3-on-6-yl-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranoside)
• CAS: 936030-66-9
• 化学式: C₃₇H₃₆O₁₆
• 分子量: 736.683
• InChiKey: SOJLKVOXHSUDPH-LMRQRCQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  53.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  198.63
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  9-[1-(2-methoxy-4-methoxycarbonylmethoxyphenyl)]-3H-xanthen-3-on-6-yl-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranoside) 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以48%的产率得到9-[1-(2-methoxy-4-methoxycarbonylmethoxyphenyl)]-3H-xanthen-3-on-6-yl-β-D-galactopyranoside
  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-hydroxy-2-methoxyphenyl)]-6-hydroxy-3H-xanthen-3-one 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 9-[1-(2-methoxy-4-methoxycarbonylmethoxyphenyl)]-3H-xanthen-3-on-6-yl-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranoside)
  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