N-[[1,8-bis[[bis(pyridin-2-ylmethyl)amino]methyl]-3-hydroxy-6-oxoxanthen-4-yl]methyl]-2-[4-[7-(diethylamino)-2-oxochromene-3-carbonyl]piperazin-1-yl]acetamide | 1246818-84-7

• 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: N-[[1,8-bis[[bis(pyridin-2-ylmethyl)amino]methyl]-3-hydroxy-6-oxoxanthen-4-yl]methyl]-2-[4-[7-(diethylamino)-2-oxochromene-3-carbonyl]piperazin-1-yl]acetamide
• CAS: 1246818-84-7
• 化学式: C₆₀H₆₀N₁₀O₇
• 分子量: 1033.2
• InChiKey: FUSNQAGZKITWJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  77
• 可旋转键数：
  20
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  187
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  N-[[1,8-bis[[bis(pyridin-2-ylmethyl)amino]methyl]-3-hydroxy-6-oxoxanthen-4-yl]methyl]-2-[4-[7-(diethylamino)-2-oxochromene-3-carbonyl]piperazin-1-yl]acetamide 、 乙酸酐 在 zinc(II) chloride 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.17h， 以7%的产率得到
  参考文献：
  名称：

  Rational Design of FRET-Based Ratiometric Chemosensors for in Vitro and in Cell Fluorescence Analyses of Nucleoside Polyphosphates

  摘要：

  Ratiometric fluorescence sensing is a useful technique for the precise and quantitative analysis of biological events occurring under complex conditions, such as those inside cells. We report herein the design of new ratiometric chemosensors for nucleoside polyphosphates such as ATP that are based on binding-induced modulation of fluorescence resonance energy transfer (FRET) coupled with a turn-on fluorescence-sensing mechanism. We designed these new FRET-based ratiometric chemosensors by utilizing spectral overlap changes to modulate the FRET efficiency. Introduction of coumarin fluorophores as the FRET donors into a binuclear zinc complex as the FRET acceptor provided the ratiometric chemosensors. These chemosensors exhibited a clear dual-mission signal change upon binding with strong affinity (K-app approximate to 10(6)-10(7) M-1) to nucleoside polyphosphates in aqueous solution, whereas no detectable emission change was observed with monophosphates and phosphodiester species or various other anions. These chemosensors were used for real-time fluorescence monitoring of enzyme reactions such as saccharide synthesis by glycosyltransferase and phosphorylation by protein kinase, both of which involve nucleoside polyphosphates as substrates. The utility of ratiometric sensing by chemosensors was further demonstrated in a fluorescence-imaging study of the nucleoside polyphosphates inside living cells, wherein we ratiometrically visualized the stimulus-responsive concentration change of ATP, an indicator of the cellular energy level.

  DOI：

  10.1021/ja103615z
• 作为产物：
  描述：

  7-(diethylamino)-3-(piperazine-1-carbonyl)-2H-chromen-2-one trifluoroacetate 、 N-((1,8-bis((bis(pyridin-2-ylmethyl)amino)methyl)-6-hydroxy-3-oxo-3H-xanthen-5-yl)methyl)-2-chloroacetamide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以6%的产率得到N-[[1,8-bis[[bis(pyridin-2-ylmethyl)amino]methyl]-3-hydroxy-6-oxoxanthen-4-yl]methyl]-2-[4-[7-(diethylamino)-2-oxochromene-3-carbonyl]piperazin-1-yl]acetamide
  参考文献：
  名称：

  Rational Design of FRET-Based Ratiometric Chemosensors for in Vitro and in Cell Fluorescence Analyses of Nucleoside Polyphosphates

  摘要：

  Ratiometric fluorescence sensing is a useful technique for the precise and quantitative analysis of biological events occurring under complex conditions, such as those inside cells. We report herein the design of new ratiometric chemosensors for nucleoside polyphosphates such as ATP that are based on binding-induced modulation of fluorescence resonance energy transfer (FRET) coupled with a turn-on fluorescence-sensing mechanism. We designed these new FRET-based ratiometric chemosensors by utilizing spectral overlap changes to modulate the FRET efficiency. Introduction of coumarin fluorophores as the FRET donors into a binuclear zinc complex as the FRET acceptor provided the ratiometric chemosensors. These chemosensors exhibited a clear dual-mission signal change upon binding with strong affinity (K-app approximate to 10(6)-10(7) M-1) to nucleoside polyphosphates in aqueous solution, whereas no detectable emission change was observed with monophosphates and phosphodiester species or various other anions. These chemosensors were used for real-time fluorescence monitoring of enzyme reactions such as saccharide synthesis by glycosyltransferase and phosphorylation by protein kinase, both of which involve nucleoside polyphosphates as substrates. The utility of ratiometric sensing by chemosensors was further demonstrated in a fluorescence-imaging study of the nucleoside polyphosphates inside living cells, wherein we ratiometrically visualized the stimulus-responsive concentration change of ATP, an indicator of the cellular energy level.

  DOI：

  10.1021/ja103615z

文献信息

• Rational Design of FRET-Based Ratiometric Chemosensors for in Vitro and in Cell Fluorescence Analyses of Nucleoside Polyphosphates
  作者：Yasutaka Kurishita、Takahiro Kohira、Akio Ojida、Itaru Hamachi

  DOI：10.1021/ja103615z

  日期：2010.9.29

  Ratiometric fluorescence sensing is a useful technique for the precise and quantitative analysis of biological events occurring under complex conditions, such as those inside cells. We report herein the design of new ratiometric chemosensors for nucleoside polyphosphates such as ATP that are based on binding-induced modulation of fluorescence resonance energy transfer (FRET) coupled with a turn-on fluorescence-sensing mechanism. We designed these new FRET-based ratiometric chemosensors by utilizing spectral overlap changes to modulate the FRET efficiency. Introduction of coumarin fluorophores as the FRET donors into a binuclear zinc complex as the FRET acceptor provided the ratiometric chemosensors. These chemosensors exhibited a clear dual-mission signal change upon binding with strong affinity (K-app approximate to 10(6)-10(7) M-1) to nucleoside polyphosphates in aqueous solution, whereas no detectable emission change was observed with monophosphates and phosphodiester species or various other anions. These chemosensors were used for real-time fluorescence monitoring of enzyme reactions such as saccharide synthesis by glycosyltransferase and phosphorylation by protein kinase, both of which involve nucleoside polyphosphates as substrates. The utility of ratiometric sensing by chemosensors was further demonstrated in a fluorescence-imaging study of the nucleoside polyphosphates inside living cells, wherein we ratiometrically visualized the stimulus-responsive concentration change of ATP, an indicator of the cellular energy level.