3-(benzyloxy)-1-[2-(dimethylamino)ethyl]-2-(hydroxymethyl)-6-methylpyridin-4(1H)-one | 1037734-73-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(benzyloxy)-1-[2-(dimethylamino)ethyl]-2-(hydroxymethyl)-6-methylpyridin-4(1H)-one
• CAS: 1037734-73-8
• 化学式: C₁₈H₂₄N₂O₃
• 分子量: 316.4
• InChiKey: FFXPGVQOEZLCMX-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  邻苯二甲酸亚胺 、 3-(benzyloxy)-1-[2-(dimethylamino)ethyl]-2-(hydroxymethyl)-6-methylpyridin-4(1H)-one 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以23%的产率得到3-(benzyloxy)-1-[2-(dimethylamino)ethyl]-6-methyl-2-phthalimidomethyl-pyridin-4(1H)-one
  参考文献：
  名称：

  Targeting the Lysosome: Fluorescent Iron(III) Chelators To Selectively Monitor Endosomal/Lysosomal Labile Iron Pools

  摘要：

  Iron-sensitive fluorescent chemosensors in combination with digital fluorescence spectroscopy have led to the identification of a distinct subcellular compartmentation of intracellular redox-active "labile" iron. To investigate the distribution of labile iron, our research has been focused on the development of fluorescent iron sensors targeting the endosomal/lysosomal system. Following the recent introduction of a series of 3-hydroxypyridin-4-one (HPO) based fluorescent probes we present here two novel HPO sensors capable of accumulating and monitoring iron exclusively in endosomal/lysosomal compartments. Flow cytometric and confocal microscopy studies in murine macrophages revealed endosomal/lysosomal sequestration of the probes and high responsiveness toward alterations of vesicular labile iron concentrations. This allowed assessment of cellular iron status with high sensitivity in response to the clinically applied medications desfenioxamine, deferiprone, and deferasirox. The probes represent a powerful class of sensors for quantitative iron detection and clinical real-time monitoring of subeellular labile iron levels in health and disease.

  DOI：

  10.1021/jm8001247
• 作为产物：
  描述：

  在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以3.99 g的产率得到3-(benzyloxy)-1-[2-(dimethylamino)ethyl]-2-(hydroxymethyl)-6-methylpyridin-4(1H)-one
  参考文献：
  名称：

  Targeting the Lysosome: Fluorescent Iron(III) Chelators To Selectively Monitor Endosomal/Lysosomal Labile Iron Pools

  摘要：

  Iron-sensitive fluorescent chemosensors in combination with digital fluorescence spectroscopy have led to the identification of a distinct subcellular compartmentation of intracellular redox-active "labile" iron. To investigate the distribution of labile iron, our research has been focused on the development of fluorescent iron sensors targeting the endosomal/lysosomal system. Following the recent introduction of a series of 3-hydroxypyridin-4-one (HPO) based fluorescent probes we present here two novel HPO sensors capable of accumulating and monitoring iron exclusively in endosomal/lysosomal compartments. Flow cytometric and confocal microscopy studies in murine macrophages revealed endosomal/lysosomal sequestration of the probes and high responsiveness toward alterations of vesicular labile iron concentrations. This allowed assessment of cellular iron status with high sensitivity in response to the clinically applied medications desfenioxamine, deferiprone, and deferasirox. The probes represent a powerful class of sensors for quantitative iron detection and clinical real-time monitoring of subeellular labile iron levels in health and disease.

  DOI：

  10.1021/jm8001247