9-{1-[4-(4-methoxycarbonylbutyloxy)-2-methylphenyl]}-6-hydroxy-3H-xanthen-3-one | 936030-69-2

• 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-methoxycarbonylbutyloxy)-2-methylphenyl]}-6-hydroxy-3H-xanthen-3-one
• 英文别名: Methyl 5-[4-(3-hydroxy-6-oxoxanthen-9-yl)-3-methylphenoxy]pentanoate
• CAS: 936030-69-2
• 化学式: C₂₆H₂₄O₆
• 分子量: 432.473
• InChiKey: XPNPYHCBHFHSLA-UHFFFAOYSA-N

物化性质

• 沸点：
  664.3±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-{1-[4-(4-methoxycarbonylbutyloxy)-2-methylphenyl]}-6-hydroxy-3H-xanthen-3-one 在 sodium hydroxide 、 caesium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 10.5h， 生成 9-{1-[4-(4-acetoxymethoxycarbonylbutyloxy)-2-methylphenyl]}-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：

  4-溴-3-甲基苯酚 在 咪唑 、 四丁基氟化铵 、 叔丁基锂 、 caesium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 5.5h， 生成 9-{1-[4-(4-methoxycarbonylbutyloxy)-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

文献信息

• Fluorescent probe
  申请人：——

  公开号：US07868147B2

  公开（公告）日：2011-01-11

  A fluorescent probe which is represented by the following formula (I): (wherein, R1 represents a monovalent substituent other than hydrogen atom, carboxy group, or sulfo group; R2 represents hydrogen atom, or a monovalent substituent; R3 and R4 each independently represents hydrogen atom or a halogen atom; and R5 represents a monovalent group which is cleaved by contact with a measuring object, provided that a combination of R1 and R2 is selected so that the oxidation potential of the benzene ring to which they bind makes (1) the compound represented by the formula (I) substantially no fluorescent before the cleavage, and (2) a compound after the cleavage, which is derived from the compound represented by the formula (I), substantially highly fluorescent after the cleavage).

  以下公式（I）代表的一种荧光探针： （其中，R1代表除氢原子、羧基或磺酸基以外的单价取代基；R2代表氢原子或单价取代基；R3和R4各自独立代表氢原子或卤素原子；R5代表通过与测量对象接触而被裂解的单价基团，前提是R1和R2的组合选择使得它们结合的苯环的氧化电位使得（1）在裂解前，由公式（I）表示的化合物基本上无荧光，并且（2）裂解后，从由公式（I）表示的化合物衍生出的化合物在裂解后基本上具有高度荧光）。
• Fluorescent Probe
  申请人：Nagano Tetsuo

  公开号：US20080014602A1

  公开（公告）日：2008-01-17

  A fluorescent probe which is represented by the following formula (I): (wherein, R 1 represents a monovalent substituent other than hydrogen atom, carboxy group, or sulfo group; R 2 represents hydrogen atom, or a monovalent substituent; R 3 and R 4 each independently represents hydrogen atom or a halogen atom; and R 5 represents a monovalent group which is cleaved by contact with a measuring object, provided that a combination of R 1 and R 2 is selected so that the oxidation potential of the benzene ring to which they bind makes (1) the compound represented by the formula (I) substantially no fluorescent before the cleavage, and (2) a compound after the cleavage, which is derived from the compound represented by the formula (I), substantially highly fluorescent after the cleavage).
• US7868147B2
  申请人：——

  公开号：US7868147B2

  公开（公告）日：2011-01-11
• An Enzymatically Activated Fluorescence Probe for Targeted Tumor Imaging
  作者：Mako Kamiya、Hisataka Kobayashi、Yukihiro Hama、Yoshinori Koyama、Marcelino Bernardo、Tetsuo Nagano、Peter L. Choyke、Yasuteru Urano

  DOI：10.1021/ja067710a

  日期：2007.4.1

  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.