5-[3,7-Bis(diethylamino)phenoxazin-10-yl]-5-oxopentanoic acid | 1192185-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 5-[3,7-Bis(diethylamino)phenoxazin-10-yl]-5-oxopentanoic acid
• CAS: 1192185-62-8
• 化学式: C₂₅H₃₃N₃O₄
• 分子量: 439.555
• InChiKey: ZOGXTVNYXSTHSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  73.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[3,7-Bis(diethylamino)phenoxazin-10-yl]-5-oxopentanoic acid 生成 sodium 5-(3,7-bis(diethylamino)-10H-phenoxazin-10-yl)-5-oxopentanoate
  参考文献：
  名称：

  Oxazine Conjugated Nanoparticle Detects in Vivo Hypochlorous Acid and Peroxynitrite Generation

  摘要：

  The current lack of suitable probes has limited the in vivo imaging of reactive oxygen/nitrogen species (ROS/RNS). ROS/RNS are often generated by ischemia-induced inflammation; defining the extent of tissue involvement or ROS/RNS-related damage would have a significant clinical impact. We present the preparation and demonstration of a fluorogenic sensor for monitoring peroxynitrite (ONOO-) and myeloperoxidase (MIPO) mediated hypochlorous acid (HOCl/OCl-) production. The sensor consists of a long circulating biocompatible nanoparticle that targets phagocytic cells in vivo and is coated with similar to 400 quenched oxazine fluorophores that are released by reaction with HOCl or ONOO- but are stable toward oxidants such as hydroxyl radical, hydrogen peroxide, and superoxide. MPO-dependent probe activation is chloride ion dependent and is negated in flow cytometry studies of MPO inhibitor treated neutrophils. Fluorescence reflectance imaging and microscopic fluorescence imaging in mouse hearts after myocardial infarction showed probe release into neutrophil-rich ischemic areas, making this ROS/RNS sensor a novel prognostic indicator.

  DOI：

  10.1021/ja903922u
• 作为产物：
  描述：

  戊二酸酐 、 恶嗪-1 在 三乙胺 作用下， 以 氯苯 为溶剂， 反应 0.5h， 生成 5-[3,7-Bis(diethylamino)phenoxazin-10-yl]-5-oxopentanoic acid
  参考文献：
  名称：

  Oxazine Conjugated Nanoparticle Detects in Vivo Hypochlorous Acid and Peroxynitrite Generation

  摘要：

  The current lack of suitable probes has limited the in vivo imaging of reactive oxygen/nitrogen species (ROS/RNS). ROS/RNS are often generated by ischemia-induced inflammation; defining the extent of tissue involvement or ROS/RNS-related damage would have a significant clinical impact. We present the preparation and demonstration of a fluorogenic sensor for monitoring peroxynitrite (ONOO-) and myeloperoxidase (MIPO) mediated hypochlorous acid (HOCl/OCl-) production. The sensor consists of a long circulating biocompatible nanoparticle that targets phagocytic cells in vivo and is coated with similar to 400 quenched oxazine fluorophores that are released by reaction with HOCl or ONOO- but are stable toward oxidants such as hydroxyl radical, hydrogen peroxide, and superoxide. MPO-dependent probe activation is chloride ion dependent and is negated in flow cytometry studies of MPO inhibitor treated neutrophils. Fluorescence reflectance imaging and microscopic fluorescence imaging in mouse hearts after myocardial infarction showed probe release into neutrophil-rich ischemic areas, making this ROS/RNS sensor a novel prognostic indicator.

  DOI：

  10.1021/ja903922u

文献信息

• Optical sensor conjugates for detecting reactive oxygen and/or reactive nitrogen species in vivo
  申请人：The General Hospital Corporation

  公开号：US10357574B2

  公开（公告）日：2019-07-23

  The present invention provides methods and compositions based on optical sensor conjugates that are useful for detecting reactive oxygen, reactive nitrogen, or both species that are a direct result of inflammation caused by tissue damage.

  本发明提供了基于光学传感器共轭物的方法和组合物，可用于检测活性氧、活性氮或这两种物质，它们是组织损伤引起炎症的直接结果。
• OPTICAL SENSOR CONJUGATES FOR DETECTING REACTIVE OXYGEN AND/OR REACTIVE NITROGEN SPECIES IN VIVO
  申请人：Hilderbrand Scott A.

  公开号：US20130149251A1

  公开（公告）日：2013-06-13

  The present invention provides methods and compositions based on optical sensor conjugates that are useful for detecting reactive oxygen, reactive nitrogen, or both species that are a direct result of inflammation caused by tissue damage.
• US9636423B2
  申请人：——

  公开号：US9636423B2

  公开（公告）日：2017-05-02