6-((N-(2-(((6-methylpyridin-2-yl)methyl)(pyridin-2-ylmethyl)amino)ethyl)-4-nitrophenyl)sulfonamido)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl bis(2,2-dimethylpropanoate) | 790235-45-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 6-((N-(2-(((6-methylpyridin-2-yl)methyl)(pyridin-2-ylmethyl)amino)ethyl)-4-nitrophenyl)sulfonamido)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl bis(2,2-dimethylpropanoate)
• CAS: 790235-45-9
• 化学式: C₅₁H₄₉N₅O₁₁S
• 分子量: 940.043
• InChiKey: KNTPUIKNWWVRPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.06
• 重原子数：
  68.0
• 可旋转键数：
  13.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  197.67
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  6-((N-(2-(((6-methylpyridin-2-yl)methyl)(pyridin-2-ylmethyl)amino)ethyl)-4-nitrophenyl)sulfonamido)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl bis(2,2-dimethylpropanoate) 在 potassium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 6-((2-(((6-methylpyridin-2-yl)methyl)(pyridin-2-ylmethyl)amino)ethyl)amino)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl bis(2,2-dimethylpropanoate)
  参考文献：
  名称：

  Selective Zinc Sensor Molecules with Various Affinities for Zn²⁺, Revealing Dynamics and Regional Distribution of Synaptically Released Zn²⁺ in Hippocampal Slices

  摘要：

  We have developed a series of fluorescent Zn2+ sensor molecules with distinct affinities for Zn2+, because biological Zn2+ concentrations vary over a wide range from sub-nanomolar to millimolar. The new sensors have Kd values in the range of 10(-8)-10(-4) M, compared with 2.7 nM for ZnAF-2. They do not fluoresce in the presence of other biologically important metal ions such as calcium or magnesium, and they can detect Zn2+ within 100 ms. In cultured cells, the fluorescence intensity of ZnAF-2 was saturated at low Zn2+ concentration, while that of ZnAF-3 (K-d = 0.79 mu M) was not saturated even at relatively high Zn2+ concentrations. In hippocampal slices, we measured synaptic release of Zn2+ in response to high-potassium-induced depolarization. ZnAF-2 showed similar levels of fluorescence increase in dentate gyrus (DG), CA3 and CA1, which were indistinguishable. However, ZnAF-3 showed a fluorescence increase only in DG. Thus, by using a combination of sensor molecules, it was demonstrated for the first time that a higher Zn2+ concentration is released in DG than in CA3 or CA1 and that we can easily visualize Zn2+ concentration over a wide range. We believe that the use of various combinations of ZnAF family members will offer unprecedented versatility for fluorescence-microscopic imaging of Zn2+ in biological applications.

  DOI：

  10.1021/ja050301e
• 作为产物：
  描述：

  4-nitro-N-(pyridin-2-ylmethyl)benzenesulfonamide 在 potassium carbonate 、 苯硫酚 、 三苯基膦 、 potassium iodide 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 26.0h， 生成 6-((N-(2-(((6-methylpyridin-2-yl)methyl)(pyridin-2-ylmethyl)amino)ethyl)-4-nitrophenyl)sulfonamido)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl bis(2,2-dimethylpropanoate)
  参考文献：
  名称：

  Selective Zinc Sensor Molecules with Various Affinities for Zn²⁺, Revealing Dynamics and Regional Distribution of Synaptically Released Zn²⁺ in Hippocampal Slices

  摘要：

  We have developed a series of fluorescent Zn2+ sensor molecules with distinct affinities for Zn2+, because biological Zn2+ concentrations vary over a wide range from sub-nanomolar to millimolar. The new sensors have Kd values in the range of 10(-8)-10(-4) M, compared with 2.7 nM for ZnAF-2. They do not fluoresce in the presence of other biologically important metal ions such as calcium or magnesium, and they can detect Zn2+ within 100 ms. In cultured cells, the fluorescence intensity of ZnAF-2 was saturated at low Zn2+ concentration, while that of ZnAF-3 (K-d = 0.79 mu M) was not saturated even at relatively high Zn2+ concentrations. In hippocampal slices, we measured synaptic release of Zn2+ in response to high-potassium-induced depolarization. ZnAF-2 showed similar levels of fluorescence increase in dentate gyrus (DG), CA3 and CA1, which were indistinguishable. However, ZnAF-3 showed a fluorescence increase only in DG. Thus, by using a combination of sensor molecules, it was demonstrated for the first time that a higher Zn2+ concentration is released in DG than in CA3 or CA1 and that we can easily visualize Zn2+ concentration over a wide range. We believe that the use of various combinations of ZnAF family members will offer unprecedented versatility for fluorescence-microscopic imaging of Zn2+ in biological applications.

  DOI：

  10.1021/ja050301e