4-methyl-2-oxo-2H-chromen-7-yl-4-nitrobenzenesulfonate

• 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: 4-methyl-2-oxo-2H-chromen-7-yl-4-nitrobenzenesulfonate
• 英文别名: (4-Methyl-2-oxochromen-7-yl) 4-nitrobenzenesulfonate
• 化学式: C₁₆H₁₁NO₇S
• 分子量: 361.332
• InChiKey: USSBJVUJSFUINR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  间苯二酚 在 磷酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-methyl-2-oxo-2H-chromen-7-yl-4-nitrobenzenesulfonate
  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

• A dual-responsive fluorescent probe for detection of fluoride ion and hydrazine based on test strips
  作者：Xiao Wang、Yanmei Zhou、Chenggong Xu、Haohan Song、Xiaobin Pang、Xiaoqiang Liu

  DOI：10.1016/j.saa.2018.12.004

  日期：2019.3

  and fluoride ion (F−) are regarded as environmental pollutants and potential carcinogens. A dual-functional fluorescent probe (probe 1) was developed for both F− and N2H4 with high selectivity and sensitivity. 1 was based on nucleophilic aromatic substitution reaction for N2H4 detection and selective cleavage of 4-nitrobenzenesulphonyl group for the determination of F−. The limits of detection of probe

  肼（N 2 H ^ 4）和氟离子（F - ）被视为环境污染物和潜在的致癌物质。一种双官能的荧光探针（探针1）是为两个F开发-和N 2 ħ 4具有高的选择性和灵敏度。1是基于对于N亲核芳族取代反应2 ħ 4检测和为F的判定4-硝基苯磺酰基的选择性裂解- 。检测探针与F的极限- N和2 H ^ 4分别为77.82 nM和29.34 nM，远低于美国环境保护局（EPA）的阈限值（TLV）。的自制测试条1与F提供的正工具-和气态Ñ 2 ħ 4在不同的系统中。共聚焦荧光图像表明1可以定量检测活PC12细胞中的N 2 H 4。有希望的是1在生命系统中对N 2 H 4成像和确定具有广阔的前景。
• Oxidized glutathione assay
  申请人：PROMEGA CORPORATION

  公开号：US10889849B2

  公开（公告）日：2021-01-12

  The present invention provides an assay for detection of oxidized glutathione (GSSG).

  本发明提供了一种检测氧化谷胱甘肽（GSSG）的方法。
• OXIDIZED GLUTATHIONE ASSAY
  申请人：Promega Corporation

  公开号：EP2611929B1

  公开（公告）日：2016-01-13
• US9816127B2
  申请人：——

  公开号：US9816127B2

  公开（公告）日：2017-11-14
• 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