2-{6-hydroxy-3-oxo-4,5-bis[(pyridin-2-ylmethylthiophen-2-yl-methylamino)methyl]-3H-xanthen-9-yl}benzoic acid | 1025880-01-6

• 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-{6-hydroxy-3-oxo-4,5-bis[(pyridin-2-ylmethylthiophen-2-yl-methylamino)methyl]-3H-xanthen-9-yl}benzoic acid
• 英文别名: Zinspy-5；2-[3-Hydroxy-6-oxo-4,5-bis[[pyridin-2-ylmethyl(thiophen-2-ylmethyl)amino]methyl]xanthen-9-yl]benzoic acid
• CAS: 1025880-01-6
• 化学式: C₄₄H₃₆N₄O₅S₂
• 分子量: 764.926
• InChiKey: LISAFEGDQHMKGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  55
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  173
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-{6-hydroxy-3-oxo-4,5-bis[(pyridin-2-ylmethylthiophen-2-yl-methylamino)methyl]-3H-xanthen-9-yl}benzoic acid 、 zinc(II) chloride 在 potassium chloride 、 1,4-哌嗪二乙磺酸 作用下， 以 水 为溶剂， 生成 (2-(6-hydroxy-3-oxo-4,5-bis[(pyridin-2-ylmethylthiophen-2-ylmethylamino)methyl]-3H-xanthen-9-yl)benzoic acid(-2H))zinc(II)
  参考文献：
  名称：

  Zinspy Sensors with Enhanced Dynamic Range for Imaging Neuronal Cell Zinc Uptake and Mobilization

  摘要：

  Thiophene moieties were incorporated into previously described Zinspy (ZS) fluorescent Zn(II) sensor motifs (Nolan, E. M.; Lippard, S. J. Inorg. Chem. 2004, 43, 8310-8317) to provide enhanced fluorescence properties, low-micromolar dissociation constants for Zn(II), and improved Zn(II) selectivity. Halogenation of the xanthenone and benzoate moieties of the fluorescein platform systematically modulates the excitation and emission profiles, pH-dependent fluorescence, Zn(II) affinity, and Zn(II) complexation rates, offering a general strategy for tuning multiple properties of xanthenone- based metal ion sensors. Extensive biological studies in cultured cells and primary neuronal cultures demonstrate 2-{6-hydroxy-3-oxo- 4,5-bis[(pyridin-2-ylmethylthiophen-2-ylmethylamino)methyl]-3H-xanthen-9-yl}benzoic acid (ZS5) to be a versatile imaging tool for detecting Zn(II) in vivo. ZS5 localizes to the mitochondria of HeLa cells and allows visualization of glutamate-mediated Zn(II) uptake in dendrites and Zn(II) release resulting from nitrosative stress in neurons.

  DOI：

  10.1021/ja065759a
• 作为产物：
  描述：

  4',5'-fluoresceindicarboxaldehyde 、 1-(pyridin-2-yl)-N-(thiophen-2-ylmethyl)methanamine 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 以38%的产率得到2-{6-hydroxy-3-oxo-4,5-bis[(pyridin-2-ylmethylthiophen-2-yl-methylamino)methyl]-3H-xanthen-9-yl}benzoic acid
  参考文献：
  名称：

  Zinspy Sensors with Enhanced Dynamic Range for Imaging Neuronal Cell Zinc Uptake and Mobilization

  摘要：

  Thiophene moieties were incorporated into previously described Zinspy (ZS) fluorescent Zn(II) sensor motifs (Nolan, E. M.; Lippard, S. J. Inorg. Chem. 2004, 43, 8310-8317) to provide enhanced fluorescence properties, low-micromolar dissociation constants for Zn(II), and improved Zn(II) selectivity. Halogenation of the xanthenone and benzoate moieties of the fluorescein platform systematically modulates the excitation and emission profiles, pH-dependent fluorescence, Zn(II) affinity, and Zn(II) complexation rates, offering a general strategy for tuning multiple properties of xanthenone- based metal ion sensors. Extensive biological studies in cultured cells and primary neuronal cultures demonstrate 2-{6-hydroxy-3-oxo- 4,5-bis[(pyridin-2-ylmethylthiophen-2-ylmethylamino)methyl]-3H-xanthen-9-yl}benzoic acid (ZS5) to be a versatile imaging tool for detecting Zn(II) in vivo. ZS5 localizes to the mitochondria of HeLa cells and allows visualization of glutamate-mediated Zn(II) uptake in dendrites and Zn(II) release resulting from nitrosative stress in neurons.

  DOI：

  10.1021/ja065759a

文献信息

• Zinspy Sensors with Enhanced Dynamic Range for Imaging Neuronal Cell Zinc Uptake and Mobilization
  作者：Elizabeth M. Nolan、Jubin W. Ryu、Jacek Jaworski、Rodney P. Feazell、Morgan Sheng、Stephen J. Lippard

  DOI：10.1021/ja065759a

  日期：2006.12.1

  Thiophene moieties were incorporated into previously described Zinspy (ZS) fluorescent Zn(II) sensor motifs (Nolan, E. M.; Lippard, S. J. Inorg. Chem. 2004, 43, 8310-8317) to provide enhanced fluorescence properties, low-micromolar dissociation constants for Zn(II), and improved Zn(II) selectivity. Halogenation of the xanthenone and benzoate moieties of the fluorescein platform systematically modulates the excitation and emission profiles, pH-dependent fluorescence, Zn(II) affinity, and Zn(II) complexation rates, offering a general strategy for tuning multiple properties of xanthenone- based metal ion sensors. Extensive biological studies in cultured cells and primary neuronal cultures demonstrate 2-6-hydroxy-3-oxo- 4,5-bis[(pyridin-2-ylmethylthiophen-2-ylmethylamino)methyl]-3H-xanthen-9-yl}benzoic acid (ZS5) to be a versatile imaging tool for detecting Zn(II) in vivo. ZS5 localizes to the mitochondria of HeLa cells and allows visualization of glutamate-mediated Zn(II) uptake in dendrites and Zn(II) release resulting from nitrosative stress in neurons.