9-[1-(4-hydroxy-2-methylphenyl)]-6-hydroxy-3H-xanthen-3-one | 847978-36-3

• 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: 9-[1-(4-hydroxy-2-methylphenyl)]-6-hydroxy-3H-xanthen-3-one
• 英文别名: 6-hydroxy-9-(4-hydroxy-2-methylphenyl)-3H-xanthen-3-one；6-hydroxy-9-(4-hydroxy-2-methylphenyl)xanthen-3-one
• CAS: 847978-36-3
• 化学式: C₂₀H₁₄O₄
• 分子量: 318.329
• InChiKey: UMQVDVRJKOFLST-UHFFFAOYSA-N

物化性质

• 沸点：
  625.4±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-[1-(4-hydroxy-2-methylphenyl)]-6-hydroxy-3H-xanthen-3-one 在 sodium hydroxide 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 9-{1-[4-(4-carboxybutyloxy)-2-methylphenyl]}-3H-xanthen-3-one-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 、 盐酸 、 叔丁基锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 3.0h， 生成 9-[1-(4-hydroxy-2-methylphenyl)]-6-hydroxy-3H-xanthen-3-one
  参考文献：
  名称：

  Highly Activatable and Rapidly Releasable Caged Fluorescein Derivatives

  摘要：

  Caged fluorophores, which recover fluorescence activity upon brief illumination with ultraviolet (UV) light, have played an important role in investigating cell lineage and cellular protein dynamics. In this paper, we report novel nitrobenzyl-caged fluorescein derivatives, based on our TokyoGreen platform (caged TokyoGreen), which have a single photoremovable protecting group, and the fluorescence quantum efficiency can be finely controlled via the photoinduced electron-transfer process before and after photoactivation. These new derivatives can be activated more rapidly and show a larger fluorescence enhancement than a traditional caged fluorescein, which is a bis-caged lactone form, upon brief UV irradiation both in the biological application and in cuvette experiments.

  DOI：

  10.1021/ja070376d

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）。
• TokyoGreen derivatives as specific and practical fluorescent probes for UDP-glucuronosyltransferase (UGT) 1A1
  作者：Takuya Terai、Rie Tomiyasu、Tomoe Ota、Tasuku Ueno、Toru Komatsu、Kenjiro Hanaoka、Yasuteru Urano、Tetsuo Nagano

  DOI：10.1039/c3cc38810g

  日期：——

  TokyoGreen (TG) derivatives were found to be efficient and specific substrates of an important drug-metabolizing enzyme, UDP-glucuronosyltransferase (UGT) 1A1. A rapid, specific, and sensitive assay of the enzyme was achieved simply by monitoring the change in fluorescence intensity. We also designed and developed the first “turn-on” fluorescent probes for UGTs.

  东京绿（TokyoGreen, TG）衍生物被发现是重要的药物代谢酶——尿苷二磷酸葡萄糖醛酸转移酶（UDP-葡萄糖醛酸转移酶 UGT）1A1的高效且特异性底物。通过简单地监测荧光强度的变化，实现了对该酶的快速、特异且敏感的检测。我们还设计并开发了首批针对UGT的“开启型”荧光探针。
• Organelle-Targetable Fluorescent Probes for Imaging Hydrogen Peroxide in Living Cells via SNAP-Tag Protein Labeling
  作者：Duangkhae Srikun、Aaron E. Albers、Christine I. Nam、Anthony T. Iavarone、Christopher J. Chang

  DOI：10.1021/ja100117u

  日期：2010.3.31

  Hydrogen peroxide (H2O2) is a potent small-molecule oxidant that can exert a diverse array of physiological and/or pathological effects within living systems depending on the timing and location of its production, accumulation, trafficking, and consumption. To help study the chemistry and biology of this reactive oxygen species (ROS) in its native cellular context, we now present a new method for monitoring local, subcellular changes in H2O2 levels by fluorescence imaging. Specifically, we have exploited the versatility of the SNAP-tag technology for site-specific protein labeling with small molecules on the surface or interior of living cells with the use of boronate-capped dyes to selectively visualize H2O2. The resulting SNAP-Peroxy-Green (SNAP-PG) probes consist of appropriately derivatized boronates bioconjugated to SNAP-tag fusion proteins. Spectroscopic measurements of the SNAP-PG constructs confirm their ability to detect H2O2 with specificity over other biologically relevant ROS. Moreover, these hybrid small-molecule/protein reporters can be used in live mammalian cells expressing SNAP-tag fusion proteins directed to the plasma membrane, nucleus, mitochondria, and endoplasmic reticulum. Imaging experiments using scanning confocal microscopy establish organelle-specific localization of the SNAP-tag probes and their fluorescence turn-on in response to changes in local H2O2 levels. This work provides a general molecular imaging platform for assaying H2O2 chemistry in living cells with subcellular resolution.
• 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).
• FLUORESCENT PROBE FOR MEASUREMENT OF GLUCURONATE TRANSFERASE
  申请人：Nagano Tetsuo

  公开号：US20100297681A1

  公开（公告）日：2010-11-25

  A fluorescent probe for measurement of UDP-glucuronosyltransferase, which comprises a fluorescein derivative, wherein in the fluorescein derivative, the 2-carboxy group on the benzene ring of fluorescein is replaced with another monovalent substituent, provided that said substituent is a substituent other than sulfo group, and the substituent does not have carboxy group or sulfo group, and wherein the fluorescein derivative may have an arbitrary substituent at a position on the benzene ring other than the 2-position, and the fluorescein derivative may have a substituent selected from the group consisting of an alkoxy group and a halogen atom at the 2-position and/or the 7-position of fluorescein.