1,8-bis[(2,2'-dipicolylamino)methyl]-6-hydroxy-3H-xanthen-3-one | 1052653-46-9

• 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: 1,8-bis[(2,2'-dipicolylamino)methyl]-6-hydroxy-3H-xanthen-3-one
• 英文别名: 1,8-Bis[[bis(pyridin-2-ylmethyl)amino]methyl]-6-hydroxyxanthen-3-one；1,8-bis[[bis(pyridin-2-ylmethyl)amino]methyl]-6-hydroxyxanthen-3-one
• CAS: 1052653-46-9
• 化学式: C₃₉H₃₄N₆O₃
• 分子量: 634.737
• InChiKey: AYWJMVZPMYETFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  48
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,8-bis[(2,2'-dipicolylamino)methyl]-6-hydroxy-3H-xanthen-3-one 在 硫酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 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：

  3,6-dihydroxy-1,8-bis[(2,2'-dipicolylamino)methyl]-9H-xanthene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.17h， 以83%的产率得到1,8-bis[(2,2'-dipicolylamino)methyl]-6-hydroxy-3H-xanthen-3-one
  参考文献：
  名称：

  使用基于呫吨的 Zn (II) 复合化学传感器开启核苷多磷酸盐的荧光传感

  摘要：

  小分子化学传感器的荧光传感是一种用于阐明各种生物物质功能的通用技术。我们现在报告了一种新的荧光化学传感器，用于使用金属 - 阴离子配位化学的核苷多磷酸盐（如 ATP）。化学传感器 1-2Zn(II) 由两个位点 2,2'-二吡啶甲胺 (Dpa)-Zn(II) 作为结合基序和呫吨作为核苷多磷酸盐的荧光传感单元组成。化学传感器 1-2Zn(II) 选择性地感应具有大荧光增强 (F/F(o) > 15) 和强结合亲和力 (K(app) 大约 = 1 x 10(6) M(-1)) 的多磷酸核苷，而没有可检测的荧光变化被单磷酸盐物质和各种其他阴离子诱导。1-2Zn(II) 的“开启”荧光基于一种新机制，这涉及结合诱导的氧杂蒽环的共轭形式从其非荧光去共轭状态恢复，这是由锌结合水的前所未有的亲核攻击形成的。1-2Zn(II) 检测多磷酸核苷的选择性和高度灵敏的能力使其能够在活细胞中 ATP 颗粒储存的荧光可视化中进行生物分析应用，证明了

  DOI：

  10.1021/ja803262w

文献信息

• Design of Ratiometric Fluorescent Probes Based on Arene-Metal-Ion Interactions and Their Application to Cd^IIand Hydrogen Sulfide Imaging in Living Cells
  作者：Ippei Takashima、Miyuki Kinoshita、Ryosuke Kawagoe、Saika Nakagawa、Manabu Sugimoto、Itaru Hamachi、Akio Ojida

  DOI：10.1002/chem.201304181

  日期：2014.2.17

  arene–metal‐ion interaction. Electronic structure calculations based on TDDFT offered a theoretical basis for the sensing mechanism, thus showing that metal ions electrostatically modulate the energy levels of the molecular orbitals of the fluorophore. A fluorescent probe was successfully applied to the ratiometric detection of the uptake of CdII ions and hydrogen sulfide (H2S) in living cells. These results

  金属离子与荧光团的芳环之间的非配位相互作用可作为一种通用的传感机制，用于检测荧光团发射变化较大的金属离子。我们报告了基于芳烃-金属离子相互作用及其生物应用的荧光探针设计。这项研究发现，具有不同荧光团和金属结合单元的各种探针在与金属离子（例如Ag I，Cd II，Hg II和Pb II）络合后显示出显着的发射红移。。配合物的X射线晶体学证实，金属离子与荧光团紧密相连，形成了芳烃与金属离子的相互作用。基于TDDFT的电子结构计算为传感机制提供了理论基础，因此表明金属离子静电调节了荧光团分子轨道的能级。荧光探针已成功地用于比例检测活细胞中Cd II 离子和硫化氢（H 2 S）的吸收。这些结果突显了芳烃基团和金属离子之间相互作用在生物学分析中的效用。
• 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.
• Turn-On Fluorescence Sensing of Nucleoside Polyphosphates Using a Xanthene-Based Zn(II) Complex Chemosensor
  作者：Akio Ojida、Ippei Takashima、Takahiro Kohira、Hiroshi Nonaka、Itaru Hamachi

  DOI：10.1021/ja803262w

  日期：2008.9.10

  fluorescence change was induced by monophosphate species and various other anions. The 'turn-on,' fluorescence of 1-2Zn(II) is based on a new mechanism, which involves the binding-induced recovery of the conjugated form of the xanthene ring from its nonfluorescent deconjugated state which was formed by an unprecedented nucleophilic attack of zinc-bound water. The selective and highly sensitive ability

  小分子化学传感器的荧光传感是一种用于阐明各种生物物质功能的通用技术。我们现在报告了一种新的荧光化学传感器，用于使用金属 - 阴离子配位化学的核苷多磷酸盐（如 ATP）。化学传感器 1-2Zn(II) 由两个位点 2,2'-二吡啶甲胺 (Dpa)-Zn(II) 作为结合基序和呫吨作为核苷多磷酸盐的荧光传感单元组成。化学传感器 1-2Zn(II) 选择性地感应具有大荧光增强 (F/F(o) > 15) 和强结合亲和力 (K(app) 大约 = 1 x 10(6) M(-1)) 的多磷酸核苷，而没有可检测的荧光变化被单磷酸盐物质和各种其他阴离子诱导。1-2Zn(II) 的“开启”荧光基于一种新机制，这涉及结合诱导的氧杂蒽环的共轭形式从其非荧光去共轭状态恢复，这是由锌结合水的前所未有的亲核攻击形成的。1-2Zn(II) 检测多磷酸核苷的选择性和高度灵敏的能力使其能够在活细胞中 ATP 颗粒储存的荧光可视化中进行生物分析应用，证明了
• Organelle-Localizable Fluorescent Chemosensors for Site-Specific Multicolor Imaging of Nucleoside Polyphosphate Dynamics in Living Cells
  作者：Yasutaka Kurishita、Takahiro Kohira、Akio Ojida、Itaru Hamachi

  DOI：10.1021/ja308754g

  日期：2012.11.14

  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.