3-(9-cyano-8-oxo-8H-acenaphtho[1,2-b]pyrrol-3-ylsulfanyl)propionic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(9-cyano-8-oxo-8H-acenaphtho[1,2-b]pyrrol-3-ylsulfanyl)propionic acid
• 英文别名: 3-(9-Cyano-8-oxoacenaphthyleno[1,2-b]pyrrol-3-yl)sulfanylpropanoic acid
• 化学式: C₁₈H₁₀N₂O₃S
• 分子量: 334.355
• InChiKey: NSODKNBRGPOYEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(二氰基亚甲基)-2-氧代苊 在 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.0h， 生成 3-(9-cyano-8-oxo-8H-acenaphtho[1,2-b]pyrrol-3-ylsulfanyl)propionic acid
  参考文献：
  名称：

  A Highly Selective Fluorescence Turn-on Sensor for Cysteine/Homocysteine and Its Application in Bioimaging

  摘要：

  We demonstrated a highly electron-deficient system 1 as a turn-on fluorescence sensor for intracellular imaging of Cys/Hcy in biological samples. On the basis of the specific nucleophilic ability of thiols of Cys and Hcy, 1 exhibited high selectivity and sensitivity for Cys/Hcy over other amino acids and thiol biomolecules. This probe is the first Cys/Hcy sensor with excitation in the visible region and turn-on (75-fold) fluorescence emission and also gives a significant increase in two-photon excited fluorescence for sensing Cys/Hcy. Moreover, confocal laser scanning microscopy and two-photon laser scanning microscopy experiments further established that 1 can be used for sensing Cys/Hcy within biological samples.

  DOI：

  10.1021/ja073140i

文献信息

• A Highly Selective Fluorescence Turn-on Sensor for Cysteine/Homocysteine and Its Application in Bioimaging
  作者：Meng Zhang、Mengxiao Yu、Fuyou Li、Minwei Zhu、Manyu Li、Yanhong Gao、Lei Li、Zhiqiang Liu、Jianping Zhang、Dengqing Zhang、Tao Yi、Chunhui Huang

  DOI：10.1021/ja073140i

  日期：2007.8.1

  We demonstrated a highly electron-deficient system 1 as a turn-on fluorescence sensor for intracellular imaging of Cys/Hcy in biological samples. On the basis of the specific nucleophilic ability of thiols of Cys and Hcy, 1 exhibited high selectivity and sensitivity for Cys/Hcy over other amino acids and thiol biomolecules. This probe is the first Cys/Hcy sensor with excitation in the visible region and turn-on (75-fold) fluorescence emission and also gives a significant increase in two-photon excited fluorescence for sensing Cys/Hcy. Moreover, confocal laser scanning microscopy and two-photon laser scanning microscopy experiments further established that 1 can be used for sensing Cys/Hcy within biological samples.