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Highly Fluorescent Green Fluorescent Protein Chromophore Analogues Made by Decorating the Imidazolone Ring
Author(s) -
Gutiérrez Sara,
MartínezLópez David,
Morón María,
Sucunza David,
Sampedro Diego,
Domingo Alberto,
Salgado Antonio,
Vaquero Juan J.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502929
Subject(s) - chromophore , fluorescence , green fluorescent protein , ring (chemistry) , chemistry , fluorescence microscope , confocal microscopy , intracellular , stereochemistry , photochemistry , biochemistry , biology , organic chemistry , physics , quantum mechanics , gene , microbiology and biotechnology
The synthesis and photophysical behavior of an unexplored family of green fluorescent protein (GFP)‐like chromophore analogues is reported. The compound ( Z )‐4‐(4‐hydroxybenzylidene)‐1‐propyl‐2‐(propylamino)‐1 H ‐imidazol‐5(4 H )‐one ( p ‐HBDNI, 2 a ) exhibits significantly enhanced fluorescence properties relative to the parent compound ( Z )‐5‐(4‐hydroxybenzylidene)‐2,3‐dimethyl‐3,5‐dihydro‐4 H ‐imidazol‐4‐one ( p ‐HBDI, 1 ). p ‐HBDNI was considered as a model system and the photophysical properties of other novel 2‐amino‐3,5‐dihydro‐4 H ‐imidazol‐4‐one derivatives were evaluated. Time‐dependent DFT calculations were carried out to rationalize the results. The analogue AIDNI ( 2 c ), in which the 4‐hydroxybenzyl group of p ‐HBDNI was replaced by an azaindole group, showed improved photophysical properties and potential for cell staining. The uptake and intracellular distribution of 2 c in living cells was investigated by confocal microscopy imaging.