sulfonefluorescein

• 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: sulfonefluorescein
• 英文别名: thiofluorescein；3',6'-Dihydroxyspiro[2-benzothiophene-3,9'-xanthene]-1-one
• 化学式: C₂₀H₁₂O₄S
• 分子量: 348.379
• InChiKey: CPWVZQHUKHITCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  92.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  sulfonefluorescein 在 sodium hypochlorite 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以0.32 mg的产率得到fluorescein disodium salt
  参考文献：
  名称：

  A Highly Specific Fluorescent Probe for Hypochlorous Acid and Its Application in Imaging Microbe-Induced HOCl Production

  摘要：

  Oxidative stress induced by reactive oxygen species (ROS) plays crucial roles in a wide range of physiological processes and is also implicated in various diseases, including cancer, chronic inflammatory diseases, and neurodegenerative disorders. Among the various ROS, hypochlorous acid (HOCl) plays as a powerful microbicidal agent in the innate immune system. The regulated production of microbicidal HOCl is required for the host to control the invading microbes. However, as a result of the highly reactive and diffusible nature of HOCl, its uncontrolled production may lead to an adverse effect on host physiology. Because of its biological importance, many efforts have been focused on developing selective fluorescent probes to image ROS. However, it is still challenging to design a fluorescent probe with exclusive selectivity toward a particular member of ROS. In the current work, we designed FBS as. a new fluorescent HOCl probe which has high selectivity, sensitivity, and short response time in a broad range of pH. Compared with other sensors, the "dual-lock" structure of FBS has an advantage of eliminating interferences from other ROS/RNS. Importantly, we further showed that our HOCl probe could be applied for the in vivo imaging of physiological HOCl production in the mucosa of live animals. This probe provides a promising tool for the study of HOCl production.

  DOI：

  10.1021/ja404649m
• 作为产物：
  描述：

  3',6'-dibromofluoran 在 劳森试剂 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 水 、 双氧水 、 potassium acetate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 甲苯 为溶剂， 反应 84.0h， 生成 sulfonefluorescein
  参考文献：
  名称：

  A Highly Specific Fluorescent Probe for Hypochlorous Acid and Its Application in Imaging Microbe-Induced HOCl Production

  摘要：

  Oxidative stress induced by reactive oxygen species (ROS) plays crucial roles in a wide range of physiological processes and is also implicated in various diseases, including cancer, chronic inflammatory diseases, and neurodegenerative disorders. Among the various ROS, hypochlorous acid (HOCl) plays as a powerful microbicidal agent in the innate immune system. The regulated production of microbicidal HOCl is required for the host to control the invading microbes. However, as a result of the highly reactive and diffusible nature of HOCl, its uncontrolled production may lead to an adverse effect on host physiology. Because of its biological importance, many efforts have been focused on developing selective fluorescent probes to image ROS. However, it is still challenging to design a fluorescent probe with exclusive selectivity toward a particular member of ROS. In the current work, we designed FBS as. a new fluorescent HOCl probe which has high selectivity, sensitivity, and short response time in a broad range of pH. Compared with other sensors, the "dual-lock" structure of FBS has an advantage of eliminating interferences from other ROS/RNS. Importantly, we further showed that our HOCl probe could be applied for the in vivo imaging of physiological HOCl production in the mucosa of live animals. This probe provides a promising tool for the study of HOCl production.

  DOI：

  10.1021/ja404649m

文献信息

• Aromatische Hydroxy- oder Thiol-Derivate von Carbonsäureestern als Lipasesubstrate
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0207252B1

  公开（公告）日：1992-07-29
• Cholesterin-esterase-Farbsubstrat
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0328029B1

  公开（公告）日：1993-12-08
• Substrate für Phospholipasen
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0331167B1

  公开（公告）日：1992-07-22
• A Highly Specific Fluorescent Probe for Hypochlorous Acid and Its Application in Imaging Microbe-Induced HOCl Production
  作者：Qingling Xu、Kyung-Ah Lee、Songyi Lee、Kyung Mi Lee、Won-Jae Lee、Juyoung Yoon

  DOI：10.1021/ja404649m

  日期：2013.7.3

  Oxidative stress induced by reactive oxygen species (ROS) plays crucial roles in a wide range of physiological processes and is also implicated in various diseases, including cancer, chronic inflammatory diseases, and neurodegenerative disorders. Among the various ROS, hypochlorous acid (HOCl) plays as a powerful microbicidal agent in the innate immune system. The regulated production of microbicidal HOCl is required for the host to control the invading microbes. However, as a result of the highly reactive and diffusible nature of HOCl, its uncontrolled production may lead to an adverse effect on host physiology. Because of its biological importance, many efforts have been focused on developing selective fluorescent probes to image ROS. However, it is still challenging to design a fluorescent probe with exclusive selectivity toward a particular member of ROS. In the current work, we designed FBS as. a new fluorescent HOCl probe which has high selectivity, sensitivity, and short response time in a broad range of pH. Compared with other sensors, the "dual-lock" structure of FBS has an advantage of eliminating interferences from other ROS/RNS. Importantly, we further showed that our HOCl probe could be applied for the in vivo imaging of physiological HOCl production in the mucosa of live animals. This probe provides a promising tool for the study of HOCl production.