4-methyl-2-oxo-2H-chromen-7-yl-2-nitrobenzenesulfonate | 1286689-78-8

• 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: 4-methyl-2-oxo-2H-chromen-7-yl-2-nitrobenzenesulfonate
• 英文别名: 4-methylumbelliferyl-2-nitrobenzenesulfonate；(4-methyl-2-oxochromen-7-yl) 2-nitrobenzenesulfonate
• CAS: 1286689-78-8
• 化学式: C₁₆H₁₁NO₇S
• 分子量: 361.332
• InChiKey: BHZGXNGUVZUBJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  116.72
• 氢给体数：
  0.0
• 氢受体数：
  7.0

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-2-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 4-Methylumbelliferone-based Fluorescent Probe for Sodium New Houttuyfonate
  作者：Xiaofeng Yang、Liping Wang、Minglei Zhao、Haiping Qi、Yao Wu

  DOI：10.1002/cjoc.201090251

  日期：——

  4‐dinitrobenzenesulfonate (4‐MUDNBS) was a nonfluorescent compound and was synthesized via the one‐step reaction of 4‐methylumbelliferone (4‐MU) with 2,4‐dinitrobenzenesulfonyl chloride. In basic media, SNH was decomposed to produce sodium sulfite, which then reacted with 4‐MUDNBS to yield highly fluorescent 4‐MU, hence leading to the fluorescence increase of the reaction solution. A linear correlation existed

  提出了一种新的鱼腥草酸钠（SNH）的荧光探针。4-甲基伞形酮-2,4-二硝基苯磺酸盐（4-MUDNBS）是一种非荧光化合物，是通过4-甲基伞形酮（4-MU）与2,4-二硝基苯磺酰氯的一步反应合成的。在碱性介质中，SNH分解生成亚硫酸钠，然后与4-MUDNBS反应生成高度荧光的4-MU，因此导致反应溶液的荧光增强。发射强度与SNH的浓度在0.5至15μg·mL -1范围内呈线性相关，检出限为0.15μg·mL -1（3δ）。讨论了取代基对探针的苯磺酰基部分的影响，并且负电性基团的存在有利于提出的裂解反应。
• 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