2-(3-methyl-4-(3-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-xanthen-9-yl)phenoxy)acetic acid | 1219603-03-8

• 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-(3-methyl-4-(3-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-xanthen-9-yl)phenoxy)acetic acid
• CAS: 1219603-03-8
• 化学式: C₂₈H₂₇BO₇
• 分子量: 486.329
• InChiKey: WAHOSXSMSBVJPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.2
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-((4-(氨基甲基)苄基)氧基)-6-氯嘧啶-2-胺 、 2-(3-methyl-4-(3-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-xanthen-9-yl)phenoxy)acetic acid 在 N,N,N',N'-Me₄-O-(7-azabenzotriazol-1-yl)uroniumPF₆ 、 diisopropylethylamine 作用下， 以 dimethylformamide 为溶剂， 以53%的产率得到N-(4-((2-amino-6-chloropyrimidin-4-yloxy)methyl)benzyl)-2-(3-methyl-4-(3-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-xanthen-9-yl)phenoxy)acetamide
  参考文献：
  名称：

  Organelle-Targetable Fluorescent Probes for Imaging Hydrogen Peroxide in Living Cells via SNAP-Tag Protein Labeling

  摘要：

  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.

  DOI：

  10.1021/ja100117u
• 作为产物：
  描述：

  tert-butyl 2-(3-methyl-4-(3-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-xanthen-9-yl)phenoxy)acetate 在 trifluoroacetic acid 作用下， 以 CH₂Cl₂ 为溶剂， 以86%的产率得到2-(3-methyl-4-(3-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-xanthen-9-yl)phenoxy)acetic acid
  参考文献：
  名称：

  Organelle-Targetable Fluorescent Probes for Imaging Hydrogen Peroxide in Living Cells via SNAP-Tag Protein Labeling

  摘要：

  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.

  DOI：

  10.1021/ja100117u