(4Z)-4-(4-(N,N-dimethylamino)benzylidene)-1-methyl-2-phenyl-1,4-dihydro-5H-imidazolin-5-one | 1177415-58-5

• 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: (4Z)-4-(4-(N,N-dimethylamino)benzylidene)-1-methyl-2-phenyl-1,4-dihydro-5H-imidazolin-5-one
• 英文别名: DMPI；(5Z)-5-[[4-(dimethylamino)phenyl]methylidene]-3-methyl-2-phenylimidazol-4-one
• CAS: 1177415-58-5
• 化学式: C₁₉H₁₉N₃O
• 分子量: 305.379
• InChiKey: MKNRUHSDPNMSFT-LGMDPLHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  35.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4Z)-4-(4-(N,N-dimethylamino)benzylidene)-1-methyl-2-phenyl-1,4-dihydro-5H-imidazolin-5-one 以 氘代氯仿 为溶剂， 反应 16.0h， 生成 (4E)-4-(4-(N,N-dimethylamino)benzylidene)-1-methyl-2-phenyl-1,4-dihydro-5H-imidazolin-5-one
  参考文献：
  名称：

  Excited State Relaxation Dynamics of Model Green Fluorescent Protein Chromophore Analogs: Evidence for Cis–Trans Isomerism

  摘要：

  Two green fluorescent protein (GFP) chromophore analogs (4Z)-4-(N,N-dimethylaminobenzylidene)-1-methyl-2-phenyl-1,4-dihydro-5H-imidazolin-5-one (DMPI) and (4Z)4-(N,N-diphenylaminobenzylidene)-1-methyl-2-phenyl-1,4-dihydro-5H-imidazolin-5-one (DPMPI) were investigated using femtosecond fluorescence up-conversion spectroscopy and quantum chemical calculations with the results being substantiated by HPLC and NMR measurements. The femtosecond fluorescence transients are found to be biexponential in nature and the time constants exhibit a significant dependence on solvent viscosity and polarity. A multicoordinate relaxation mechanism is proposed for the excited state relaxation behavior of the model GFP analogs. The first time component (tau(1)) was assigned to the formation of twisted intramolecular charge transfer (TICT) state along the rotational coordinate of N-substituted amine group. Time resolved intensity normalized and area normalized emission spectra (TRES and TRANES) were constructed to authenticate the occurrence of TICT state in subpicosecond time scale. Another picosecond time component (tau(2)) was attributed to internal conversion via large amplitude motion along the exomethylenic double bond which has been enunciated by quantum chemical calculations. Quantum chemical calculation also forbids the involvement of hula-twist because of high activation barrier of twisting. HPLC profiles and proton-NMR measurements of the irradiated analogs confirm the presence of Z and E isomers, whose possibility of formation can be accomplished only by the rotation along the exomethylenic double bond. The present observations can be extended to p-HBDI in order to understand the role of protein scaffold in reducing the nonradiative pathways, leading to highly luminescent nature of GFP.

  DOI：

  10.1021/jp206815t

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.