(Z)-4-(3,5-dichloro-4-hydroxybenzylidene)-1,2-dimethyl-1H-imidazol-5(4H)-one | 1241390-31-7

• 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: (Z)-4-(3,5-dichloro-4-hydroxybenzylidene)-1,2-dimethyl-1H-imidazol-5(4H)-one
• 英文别名: (5Z)-5-[(3,5-dichloro-4-hydroxyphenyl)methylidene]-2,3-dimethylimidazol-4-one
• CAS: 1241390-31-7
• 化学式: C₁₂H₁₀Cl₂N₂O₂
• 分子量: 285.13
• InChiKey: SFNOAXFLBJXEGI-YHYXMXQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-吡啶甲醛 、 (Z)-4-(3,5-dichloro-4-hydroxybenzylidene)-1,2-dimethyl-1H-imidazol-5(4H)-one 在 zinc(II) chloride 作用下， 以 1,4-二氧六环 为溶剂， 以65%的产率得到5-((Z)-3,5-dichloro-4-hydroxybenzylidene)-3-methyl-2-((E)-2-(pyridin-4-yl)vinyl)-3,5-dihydro-4H-imidazol-4-one
  参考文献：
  名称：

  基于GFP类发色团的FAST荧光激活蛋白的红移底物

  摘要：

  提出了用于活细胞显微镜的遗传编码的荧光标签。该标签由先前发布的荧光激活蛋白FAST和绿色荧光蛋白（GFP）样发色团的新型荧光衍生物组成，具有红色荧光。新型氟和FAST的可逆结合伴随着红色荧光（580-650 nm）增加了三个数量级。与以前发表的flugen：FAST复合物相比，所提出的染料可立即染色与FAST融合的靶细胞蛋白，在很短的时间内被洗掉，并在共聚焦和宽视野显微镜中显示出更高的荧光信号光稳定性。

  DOI：

  10.1002/chem.201901151
• 作为产物：
  描述：

  3,5-二氯-4-羟基苯甲醛 在 sodium acetate 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 (Z)-4-(3,5-dichloro-4-hydroxybenzylidene)-1,2-dimethyl-1H-imidazol-5(4H)-one
  参考文献：
  名称：

  Plug-and-Play Fluorophores Extend the Spectral Properties of Spinach

  摘要：

  Spinach and Spinach2 are RNA aptamers that can be used for the genetic encoding of fluorescent RNA. Spinach2 binds and activates the fluorescence of (Z)-4-(3,5-difluoro-4-hydroxybenzylidene)-1,2-dimethyl-1H-imidazol-5 (4H)-one (DFHBI), allowing the dynamic localizations of Spinach2-tagged RNAs to be imaged in live cells. The spectral properties of Spinach2 are limited by DFHBI, which produces fluorescence that is bluish-green and is not optimized for filters commonly used in fluorescence microscopes. Here we characterize the structural features that are required for fluorophore binding to Spinach2 and describe novel fluorophores that bind and are switched to a fluorescent state by Spinach2. These diverse Spinach2 fluorophore complexes exhibit fluorescence that is more compatible with existing microscopy filter sets and allows Spinach2-tagged constructs to be imaged with either GFP or YFP filter cubes. Thus, these "plug-and-play" fluorophores allow the spectral properties of Spinach2 to be altered on the basis of the specific spectral needs of the experiment.

  DOI：

  10.1021/ja410819x

文献信息

• COUPLED RECOGNITION/DETECTION SYSTEM FOR IN VIVO AND IN VITRO USE
  申请人：Cornell University

  公开号：US20190185434A1

  公开（公告）日：2019-06-20

  The present invention relates to novel fluorophores and their use in combination with novel nucleic acid molecules, called aptamers, that bind specifically to the fluorophore and thereby enhance the fluorescence signal of the fluorophore upon exposure to radiation of suitable wavelength. Molecular complexes formed between the novel fluorophores, novel nucleic acid molecules, and their target molecules are described, and the use of multivalent aptamer constructs as fluorescent sensors for target molecules of interest are also described.

  本发明涉及新型荧光物质及其与称为寡核苷酸的新型核酸分子结合使用，这些寡核苷酸能够特异性地结合到荧光物质上，从而在受到适当波长辐射照射时增强荧光物质的荧光信号。描述了新型荧光物质、新型核酸分子及其靶分子形成的分子复合物，还描述了多价寡核苷酸构建物作为感兴趣的靶分子的荧光传感器的使用。
• Coupled recognition/detection system for in vivo and in vitro use
  申请人：Jaffrey Samie R.

  公开号：US10316000B2

  公开（公告）日：2019-06-11

  The present invention relates to novel fluorophores and their use in combination with novel nucleic acid molecules, called aptamers, that bind specifically to the fluorophore and thereby enhance the fluorescence signal of the fluorophore upon exposure to radiation of suitable wavelength. Molecular complexes formed between the novel fluorophores, novel nucleic acid molecules, and their target molecules are described, and the use of multivalent aptamer constructs as fluorescent sensors for target molecules of interest are also described.

  本发明涉及新型荧光团及其与新型核酸分子（称为适配体）的结合使用，后者与荧光团特异性结合，从而在暴露于适当波长的辐射时增强荧光团的荧光信号。此外，还介绍了新型荧光团、新型核酸分子及其目标分子之间形成的分子复合物，以及多价适配体构建体作为荧光传感器用于检测感兴趣的目标分子的情况。
• [EN] COUPLED RECOGNITION/DETECTION SYSTEM FOR IN VIVO AND IN VITRO USE<br/>[FR] SYSTÈME DE RECONNAISSANCE/DÉTECTION COUPLÉE POUR UNE UTILISATION IN VIVO ET IN VITRO
  申请人：UNIV CORNELL

  公开号：WO2010096584A1

  公开（公告）日：2010-08-26

  The present invention relates to novel fluorophores and their use in combination with novel nucleic acid molecules, called aptamers, that bind specifically to the fluorophore and thereby enhance the fluorescence signal of the fluorophore upon exposure to radiation of suitable wavelength. Molecular complexes formed between the novel fluorophores, novel nucleic acid molecules, and their target molecules are described, and the use of multivalent aptamer constructs as fluorescent sensors for target molecules of interest are also described.
• Red‐Shifted Substrates for FAST Fluorogen‐Activating Protein Based on the GFP‐Like Chromophores
  作者：Natalia V. Povarova、Snizhana O. Zaitseva、Nadezhda S. Baleeva、Alexander Yu. Smirnov、Ivan N. Myasnyanko、Marina B. Zagudaylova、Nina G. Bozhanova、Dmitriy A. Gorbachev、Kseniya K. Malyshevskaya、Alexey S. Gavrikov、Alexander S. Mishin、Mikhail S. Baranov

  DOI：10.1002/chem.201901151

  日期：2019.7.22

  A genetically encoded fluorescent tag for live cell microscopy is presented. This tag is composed of previously published fluorogen‐activating protein FAST and a novel fluorogenic derivative of green fluorescent protein (GFP)‐like chromophore with red fluorescence. The reversible binding of the novel fluorogen and FAST is accompanied by three orders of magnitude increase in red fluorescence (580–650 nm)

  提出了用于活细胞显微镜的遗传编码的荧光标签。该标签由先前发布的荧光激活蛋白FAST和绿色荧光蛋白（GFP）样发色团的新型荧光衍生物组成，具有红色荧光。新型氟和FAST的可逆结合伴随着红色荧光（580-650 nm）增加了三个数量级。与以前发表的flugen：FAST复合物相比，所提出的染料可立即染色与FAST融合的靶细胞蛋白，在很短的时间内被洗掉，并在共聚焦和宽视野显微镜中显示出更高的荧光信号光稳定性。
• Plug-and-Play Fluorophores Extend the Spectral Properties of Spinach
  作者：Wenjiao Song、Rita L. Strack、Nina Svensen、Samie R. Jaffrey

  DOI：10.1021/ja410819x

  日期：2014.1.29

  Spinach and Spinach2 are RNA aptamers that can be used for the genetic encoding of fluorescent RNA. Spinach2 binds and activates the fluorescence of (Z)-4-(3,5-difluoro-4-hydroxybenzylidene)-1,2-dimethyl-1H-imidazol-5 (4H)-one (DFHBI), allowing the dynamic localizations of Spinach2-tagged RNAs to be imaged in live cells. The spectral properties of Spinach2 are limited by DFHBI, which produces fluorescence that is bluish-green and is not optimized for filters commonly used in fluorescence microscopes. Here we characterize the structural features that are required for fluorophore binding to Spinach2 and describe novel fluorophores that bind and are switched to a fluorescent state by Spinach2. These diverse Spinach2 fluorophore complexes exhibit fluorescence that is more compatible with existing microscopy filter sets and allows Spinach2-tagged constructs to be imaged with either GFP or YFP filter cubes. Thus, these "plug-and-play" fluorophores allow the spectral properties of Spinach2 to be altered on the basis of the specific spectral needs of the experiment.