S-(2,4-Dinitrophenyl)-cystein | 3165-76-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S-(2,4-Dinitrophenyl)-cystein
• 英文别名: 2-Amino-3-(2,4-dinitrophenyl)sulfanylpropanoic acid
• CAS: 3165-76-2
• 化学式: C₉H₉N₃O₆S
• 分子量: 287.253
• InChiKey: QGTPCMCCGCVZQY-UHFFFAOYSA-N

物化性质

• 沸点：
  497.7±45.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  180
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-(3-hydroxypropyl)-2,4-dinitrobenzenesulfonamide 在 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三苯基膦 作用下， 以 aq. phosphate buffer 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.5h， 生成 S-(2,4-Dinitrophenyl)-cystein
  参考文献：
  名称：

  硫醇活化的二氧化硫（SO 2）前药作为MRSA抑制剂

  摘要：

  耐药感染在世界范围内变得越来越普遍，并且新的药物开发策略是必需的。在这里，我们报告2，4-二硝基苯磺酰胺的合成和评估，这是一种活性硫物质二氧化硫（SO 2）的供体，作为耐甲氧西林的金黄色葡萄球菌（MRSA）抑制剂。N-（3-甲氧基苯基）-2,4-二硝基-N-（prop-2-yn-1-yl）苯磺酰胺（5e）具有优异的体外MRSA抑制能力。该化合物具有细胞渗透性，并用5e耗尽的细胞内硫醇和增强的氧化物种处理MRSA细胞，两者的结果均与涉及硫醇活化以产生SO 2的机理一致。

  DOI：

  10.1016/j.bmcl.2015.04.046

文献信息

• Two chemodosimeters for fluorescence recognition of biothiols in aqueous solution and their bioimaging application
  作者：Wei Du、Rui-Juan Liu、Jianguo Fang、Hong Gao、Ya-Wen Wang、Yu Peng

  DOI：10.1016/j.tet.2019.130477

  日期：2019.9

  Two fluorescein derivatives containing 2,4-dinitrobenzenesulfonyl group have been developed as fluorescent probes to detect the biothiols (Cys, Hcy and GSH) in aqueous solution. Probes 1 and 2 can distinguish these biothiols in the presence of other amino acids. While probe 1 can recognize the biothiols in PBS/DMSO (v:v = 95:5, pH = 7.40) solution, notably probe 2 could be used in PBS buffer solution

  已经开发出两种含有2，4-二硝基苯磺酰基的荧光素衍生物作为荧光探针，以检测水溶液中的生物硫醇（Cys，Hcy和GSH）。探针1和2可以在其他氨基酸存在下区分这些生物硫醇。虽然探针1可以识别PBS / DMSO（v：v = 95：5，pH = 7.40）溶液中的生物硫醇，但值得注意的是探针2可以用于PBS缓冲溶液（pH = 7.40）。半胱氨酸的用于探针的检测限2在0.021达到 μ水溶液中的M低于胞内Cys浓度。在识别过程中，探针与生物硫醇之间发生了反应，其中S-O键被裂解以去除2，4-二硝基苯磺酰基。的数据1 H NMR，MS和DFT / TD-DFT计算进一步证实了检测机制。此外，两种探针已成功应用于HeLa细胞成像。
• Nile-Red-Based Fluorescence Probe for Selective Detection of Biothiols, Computational Study, and Application in Cell Imaging
  作者：Xiang Rong、Zhong-Yong Xu、Jin-Wu Yan、Zhi-Zhong Meng、Bin Zhu、Lei Zhang

  DOI：10.3390/molecules25204718

  日期：——

  A new colorimetric and fluorescence probe NRSH based on Nile-red chromophore for the detection of biothiols has been developed, exhibiting high selectivity towards biothiols over other interfering species. NRSH shows a blue shift in absorption peak upon reacting with biothiols, from 587 nm to 567 nm, which induces an obvious color change from blue to pink and exhibits a 35-fold fluorescence enhancement at 645 nm in red emission range. NRSH displays rapid (<1 min) response for H2S, which is faster than other biothiols (>5 min). The detection limits of probe NRSH towards biothiols are very low (22.05 nM for H2S, 34.04 nM for Cys, 107.28 nM for GSH and 113.65 nM for Hcy). Furthermore, NRSH is low cytotoxic and can be successfully applied as a bioimaging tool for real-time monitoring biothiols in HeLa cells. In addition, fluorescence mechanism of probe NRSH is further understood by theoretical calculations.

  基于尼罗红色团的新型比色和荧光探针NRSH已开发出来，用于生物硫醇的检测，对生物硫醇具有高选择性，而对其他干扰物质则不敏感。NRSH在与生物硫醇反应后，吸收峰向蓝色移动，从587nm到567nm，引起明显的颜色变化，从蓝色变为粉红色，并在红色发射范围内的645nm处展现35倍的荧光增强。NRSH对H2S的响应速度快（<1分钟），比其他生物硫醇（>5分钟）更快。探针NRSH对生物硫醇的检测限非常低（H2S 22.05nM，Cys 34.04nM，GSH 107.28nM和Hcy 113.65nM）。此外，NRSH细胞毒性低，可成功应用于HeLa细胞中实时监测生物硫醇的生物成像工具。此外，通过理论计算，进一步了解了探针NRSH的荧光机制。
• Stimuli-Responsive Polymer Film that Autonomously Translates a Molecular Detection Event into a Macroscopic Change in Its Optical Properties via a Continuous, Thiol-Mediated Self-Propagating Reaction
  作者：Hemakesh Mohapatra、Hyungwoo Kim、Scott T. Phillips

  DOI：10.1021/jacs.5b08582

  日期：2015.10.7

  This Communication describes a chemically responsive polymer film that is capable of detecting low levels of a specific applied molecular signal (thiol) and subsequently initiating a self-propagating reaction within the material that converts the nonfluorescent film into a globally fluorescent material. We illustrate that the intensity of the resulting fluorescent material is independent of the quantity of the applied thiol, whereas the rate to reach the maximum level of signal is directly proportional to the quantity of the signal. In contrast, a control film, which lacks functionality for mediating the self-propagating reaction, provides a maximum change in fluorescence that is directly proportional to the quantity of the applied thiol. This level of nonamplified signal is 78% lower in intensity (when initiated with 100 mu M of applied thiol) than is achieved when the material contains functionality that supports the self-powered, self-propagating amplification reaction.
• US5578470A
  申请人：——

  公开号：US5578470A

  公开（公告）日：1996-11-26
• Thiol activated prodrugs of sulfur dioxide (SO2) as MRSA inhibitors
  作者：Kundansingh A. Pardeshi、Satish R. Malwal、Ankita Banerjee、Surobhi Lahiri、Radha Rangarajan、Harinath Chakrapani

  DOI：10.1016/j.bmcl.2015.04.046

  日期：2015.7

  are becoming common worldwide and new strategies for drug development are necessary. Here, we report the synthesis and evaluation of 2,4-dinitrophenylsulfonamides, which are donors of sulfur dioxide (SO2), a reactive sulfur species, as methicillin-resistant Staphylococcus aureus (MRSA) inhibitors. N-(3-Methoxyphenyl)-2,4-dinitro-N-(prop-2-yn-1-yl)benzenesulfonamide (5e) was found to have excellent in

  耐药感染在世界范围内变得越来越普遍，并且新的药物开发策略是必需的。在这里，我们报告2，4-二硝基苯磺酰胺的合成和评估，这是一种活性硫物质二氧化硫（SO 2）的供体，作为耐甲氧西林的金黄色葡萄球菌（MRSA）抑制剂。N-（3-甲氧基苯基）-2,4-二硝基-N-（prop-2-yn-1-yl）苯磺酰胺（5e）具有优异的体外MRSA抑制能力。该化合物具有细胞渗透性，并用5e耗尽的细胞内硫醇和增强的氧化物种处理MRSA细胞，两者的结果均与涉及硫醇活化以产生SO 2的机理一致。