7-(2,4-dinitrophenoxy)-3-benzo[d]thiazol-2-yl coumarin | 1221678-24-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(2,4-dinitrophenoxy)-3-benzo[d]thiazol-2-yl coumarin
• 英文别名: 3-(benzothiazol-2yl)-7-(2,4-dinitrophenoxy)coumarin；3-(1,3-Benzothiazol-2-yl)-7-(2,4-dinitrophenoxy)chromen-2-one；3-(1,3-benzothiazol-2-yl)-7-(2,4-dinitrophenoxy)chromen-2-one
• CAS: 1221678-24-5
• 化学式: C₂₂H₁₁N₃O₇S
• 分子量: 461.411
• InChiKey: HCSIUMNTNWMZNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  168
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-(2-benzothiazolyl)-7-hydroxy-2-iminocoumarin 在 盐酸 、 水 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-(2,4-dinitrophenoxy)-3-benzo[d]thiazol-2-yl coumarin
  参考文献：
  名称：

  Selective Selenol Fluorescent Probes: Design, Synthesis, Structural Determinants, and Biological Applications

  摘要：

  Selenium (Se) is an essential micronutrient element, and the biological significance of Se is predominantly dependent on its incorporation as selenocysteine (Sec), the genetically encoded 21st amino acid in protein synthesis, into the active site of selenoproteins, which have broad functions, ranging from redox regulation and anti-inflammation to the production of active thyroid hormones. Compared to its counterpart Cys, there are only limited probes for selective recognition of Sec, and such selectivity is strictly restricted at low pH conditions. We reported herein the design, synthesis, and biological evaluations of a series of potential Sec probes based on the mechanism of nucleophilic aromatic substitution. After the initial screening, the structural determinants for selective recognition of Sec were recapitulated. The follow-up studies identified that probe 19 (Sel-green) responds to Sec and other selenols with more than 100-fold increase of emission in neutral aqueous solution (pH 7.4), while there is no significant interference from the biological thiols, amines, or alcohols. Sel-green was successfully applied to quantify the Sec content in the selenoenzyme thioredoxin reductase and image endogenous Sec in live HepG2 cells. With the aid of Sel-green, we further demonstrated that the cytotoxicity of different selenocompounds is correlated to their ability metabolizing to selenols in cells. To the best of our knowledge, Sel-green is the first selenol probe that works under physiological conditions. The elucidation of the structure-activity relationship for selective recognition of selenols paves the way for further design of novel probes to better understand the pivotal role of Sec as well as selenoproteins in vivo

  DOI：

  10.1021/ja5099676

文献信息

• New insights into the water-solubilization of thiol-sensitive fluorogenic probes based on long-wavelength 7-hydroxycoumarin scaffolds
  作者：Benoît Roubinet、Pierre-Yves Renard、Anthony Romieu

  DOI：10.1016/j.dyepig.2014.02.004

  日期：2014.11

  The synthesis and photophysical properties of novel water-soluble phenol-based fluorophores derived from 3-benzothiazolyl-7-hydroxycoumarin and emitting in the range 485–631 nm are described. Further conversion into thiol-sensitive fluorogenic probes through the chemical modification of their hydroxyl group was next investigated. Depending on the type of thiol-reactive quenching moiety used (2,4-d

  描述了衍生自3-苯并噻唑基-7-羟基香豆素并在485–631 nm范围内发射的新型水溶性酚基荧光团的合成和光物理性质。接下来研究通过其羟基的化学修饰进一步转化为对硫醇敏感的荧光探针的方法。根据所用硫醇反应性淬灭基团的类型（2,4-二硝基苯磺酰基酯，2,4-二硝基苯基醚或苯醌型迈克尔受体）和预先引入香豆素核心的水溶性基团，在生理条件下，观察到这些前荧光团的巯基诱导的荧光活化的差异。
• A highly sensitive fluorescent probe for detection of benzenethiols in environmental samples and living cells
  作者：Weiying Lin、Lingliang Long、Wen Tan

  DOI：10.1039/b922478e

  日期：——

  A highly sensitive fluorescent probe with a detection limit of 1.8 × 10−9 M was constructed and employed to detect benzenethiols in environmental samples and living cells.

  研究人员制造了一种灵敏度极高的荧光探针，其检测限为1.8×10-9M，用于检测环境样本和活细胞中的苯硫醇。
• Selective Selenol Fluorescent Probes: Design, Synthesis, Structural Determinants, and Biological Applications
  作者：Baoxin Zhang、Chunpo Ge、Juan Yao、Yaping Liu、Huichen Xie、Jianguo Fang

  DOI：10.1021/ja5099676

  日期：2015.1.21

  Selenium (Se) is an essential micronutrient element, and the biological significance of Se is predominantly dependent on its incorporation as selenocysteine (Sec), the genetically encoded 21st amino acid in protein synthesis, into the active site of selenoproteins, which have broad functions, ranging from redox regulation and anti-inflammation to the production of active thyroid hormones. Compared to its counterpart Cys, there are only limited probes for selective recognition of Sec, and such selectivity is strictly restricted at low pH conditions. We reported herein the design, synthesis, and biological evaluations of a series of potential Sec probes based on the mechanism of nucleophilic aromatic substitution. After the initial screening, the structural determinants for selective recognition of Sec were recapitulated. The follow-up studies identified that probe 19 (Sel-green) responds to Sec and other selenols with more than 100-fold increase of emission in neutral aqueous solution (pH 7.4), while there is no significant interference from the biological thiols, amines, or alcohols. Sel-green was successfully applied to quantify the Sec content in the selenoenzyme thioredoxin reductase and image endogenous Sec in live HepG2 cells. With the aid of Sel-green, we further demonstrated that the cytotoxicity of different selenocompounds is correlated to their ability metabolizing to selenols in cells. To the best of our knowledge, Sel-green is the first selenol probe that works under physiological conditions. The elucidation of the structure-activity relationship for selective recognition of selenols paves the way for further design of novel probes to better understand the pivotal role of Sec as well as selenoproteins in vivo