N-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen]-2-yl)picolinamide | 1266715-64-3

• 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-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen]-2-yl)picolinamide
• 英文别名: N-[3',6'-bis(diethylamino)-3-oxospiro[isoindole-1,9'-xanthene]-2-yl]pyridine-2-carboxamide
• CAS: 1266715-64-3
• 化学式: C₃₄H₃₅N₅O₃
• 分子量: 561.684
• InChiKey: YVCGLPYILWTVAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  78
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  iron perchlorate hexahydrate 、 N-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen]-2-yl)picolinamide 以 乙醇 为溶剂， 以41%的产率得到
  参考文献：
  名称：

  A Turn-on Fluorescent Iron Complex and Its Cellular Uptake

  摘要：

  In the treatment of chronic iron overload disorders, ligands capable of complexing so-called "labile" (nonprotein bound) Fe are required to enter iron-loaded cells, sequester excess Fe, and then exit the cell (and the body) as an intact Fe complex. Despite the emergence of several ligand families that show high activity in mobilizing intracellular Fe, the mechanism and the locations of these subcellular labile Fe pools are still poorly understood. Our previous studies have unearthed a class of heterocyclic hydrazine-based chelators (e.g., benzoyl picolinoyl hydrazine, H2BPH) that show excellent activity at mobilizing Fe from Fe-loaded cells. Herein, we have grafted a fluorescent tag (rhodamine B) onto H2BPH to generate a ligand (L-1) that is nonfluorescent in its uncomplexed form but becomes strongly fluorescent in complex with Fe-III. The free ligand and its 1:2 Fe complex [Fe-III(L-1)(2)](3+) have both been fully characterized spectroscopically and with X-ray crystallography. Confocal fluorescent microscopy of HeLa cells incubated with [Fe-III(L-1)(2))(3+) shows that the complex rapidly enters HeLa cells and localizes within endosomes/lysosomes.

  DOI：

  10.1021/ic201495r
• 作为产物：
  描述：

  N-(Rhodamine-B) lactam-hydrazine 、 以 乙腈 为溶剂， 以1.75 g的产率得到N-(3',6'-bis(diethylamino)-3-oxospiro[isoindoline-1,9'-xanthen]-2-yl)picolinamide
  参考文献：
  名称：

  A Turn-on Fluorescent Iron Complex and Its Cellular Uptake

  摘要：

  In the treatment of chronic iron overload disorders, ligands capable of complexing so-called "labile" (nonprotein bound) Fe are required to enter iron-loaded cells, sequester excess Fe, and then exit the cell (and the body) as an intact Fe complex. Despite the emergence of several ligand families that show high activity in mobilizing intracellular Fe, the mechanism and the locations of these subcellular labile Fe pools are still poorly understood. Our previous studies have unearthed a class of heterocyclic hydrazine-based chelators (e.g., benzoyl picolinoyl hydrazine, H2BPH) that show excellent activity at mobilizing Fe from Fe-loaded cells. Herein, we have grafted a fluorescent tag (rhodamine B) onto H2BPH to generate a ligand (L-1) that is nonfluorescent in its uncomplexed form but becomes strongly fluorescent in complex with Fe-III. The free ligand and its 1:2 Fe complex [Fe-III(L-1)(2)](3+) have both been fully characterized spectroscopically and with X-ray crystallography. Confocal fluorescent microscopy of HeLa cells incubated with [Fe-III(L-1)(2))(3+) shows that the complex rapidly enters HeLa cells and localizes within endosomes/lysosomes.

  DOI：

  10.1021/ic201495r

文献信息

• Highly sensitive and selective turn-on fluorescent and chromogenic probe for Cu²⁺and ClO⁻based on a N-picolinyl rhodamine B-hydrazide derivative
  作者：Yunlong Liu、Yue Sun、Jun Du、Xin Lv、Yun Zhao、Maliang Chen、Pi Wang、Wei Guo

  DOI：10.1039/c0ob00411a

  日期：——

  A new rhodamine B-based dual-function chromo- and fluorogenic probe for Cu2+ and ClO− has been designed, synthesized, and characterized. The probe comprises a spectroscopic unit of rhodamine B and a Cu2+-specific chelating unit of pyridinecarboxamide as well as a ClO−-specific reactive moiety of diacylhydrazine, and is a highly selective and extremely sensitive fluorescent and colorimetric sensor for

  对Cu新的基于乙罗丹明双功能生色和荧光探针2+和C10 -已被设计，合成和表征。该探针包括一个光谱单元罗丹明B和Cu 2+特有的螯合单元吡啶甲酰胺以及一个CLO -二酰基肼的特异性反应性部分，并且是用于铜一种高选择性和非常敏感的荧光和比色传感器2 +和C10 -在不同的pH条件下。与铜的报道探针相比2+或C10 - ，这是一种基于小分子可以检测的Cu的第一化学传感器2+和C10 -分别以1nM的水平。
• A Turn-on Fluorescent Iron Complex and Its Cellular Uptake
  作者：Jy D. Chartres、Michael Busby、Mark J. Riley、Jason J. Davis、Paul V. Bernhardt

  DOI：10.1021/ic201495r

  日期：2011.9.19

  In the treatment of chronic iron overload disorders, ligands capable of complexing so-called "labile" (nonprotein bound) Fe are required to enter iron-loaded cells, sequester excess Fe, and then exit the cell (and the body) as an intact Fe complex. Despite the emergence of several ligand families that show high activity in mobilizing intracellular Fe, the mechanism and the locations of these subcellular labile Fe pools are still poorly understood. Our previous studies have unearthed a class of heterocyclic hydrazine-based chelators (e.g., benzoyl picolinoyl hydrazine, H2BPH) that show excellent activity at mobilizing Fe from Fe-loaded cells. Herein, we have grafted a fluorescent tag (rhodamine B) onto H2BPH to generate a ligand (L-1) that is nonfluorescent in its uncomplexed form but becomes strongly fluorescent in complex with Fe-III. The free ligand and its 1:2 Fe complex [Fe-III(L-1)(2)](3+) have both been fully characterized spectroscopically and with X-ray crystallography. Confocal fluorescent microscopy of HeLa cells incubated with [Fe-III(L-1)(2))(3+) shows that the complex rapidly enters HeLa cells and localizes within endosomes/lysosomes.