N-((1,8-bis((bis(pyridin-2-ylmethyl)amino)methyl)-6-hydroxy-3-oxo-3H-xanthen-5-yl)methyl)-2-chloroacetamide | 1246818-87-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-((1,8-bis((bis(pyridin-2-ylmethyl)amino)methyl)-6-hydroxy-3-oxo-3H-xanthen-5-yl)methyl)-2-chloroacetamide
• CAS: 1246818-87-0
• 化学式: C₄₂H₃₈ClN₇O₄
• 分子量: 740.261
• InChiKey: BJIKGCHKXVIMPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  54.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  137.58
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  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 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成
  参考文献：
  名称：

  Organelle-Localizable Fluorescent Chemosensors for Site-Specific Multicolor Imaging of Nucleoside Polyphosphate Dynamics in Living Cells

  摘要：

  ATP and its derivatives (nucleoside polyphosphates (NPPs)) are implicated in many biological events, so their rapid and convenient detection is important. In particular, live cell detection of NPPs at specific local regions of cells could greatly contribute understanding of the complicated roles of NPPs. We report herein the design of two new fluorescent chemosensors that detect the dynamics of NPPs in specific regions of living cells. To achieve imaging of NPPs on plasma membrane surfaces (2-2Zn(II)), a lipid anchor was introduced into xanthene-based, Zn(II) complex 1-2Zn(II); which was previously developed as a turn-on type fluorescent chemosensor for NPPs. Meanwhile, for subcellular imaging of ATP in mitochondria, we designed rhodamine-type complex 3-2Zn(II); which possesses a cationic. pyronin ring instead of xanthene Detailed spectroscopic, studies revealed that 2-2Zn(II) and 3-2Zn(II) can sense NPPs with a several-fold increase of their fluorescence intensities: through a sensing mechanism similar to 1-2Zn(II), involving binding induced recovery of the Conjugated form of the xantliene or pyronin ring: In live cell imaging, 2-2Zn(II) containing a lipid anchor selectively localized on the plasma membrane surface and detected the extracellular release of NPPs during cell necrosis induced by streptolysin O. on the other hand, rhodamine-type complex 3-2Zn(II) Spontaneously localized at mitochondria inside cells, and sensed the local increase of ATP concentration during apoptosis., Multicolor images were obtained through simultaneous use of 2-2Zn(II) and 3-2Zn(II), allowing detection of the dynamics of ATP in different cellular compartments at the same time.

  DOI：

  10.1021/ja308754g
• 作为产物：
  描述：

  氯乙酰胺-N-甲醇 、 1,8-bis[(2,2'-dipicolylamino)methyl]-6-hydroxy-3H-xanthen-3-one 以 硫酸 为溶剂， 反应 30.0h， 以20%的产率得到N-((1,8-bis((bis(pyridin-2-ylmethyl)amino)methyl)-6-hydroxy-3-oxo-3H-xanthen-5-yl)methyl)-2-chloroacetamide
  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