Highly Fluorescent Green Fluorescent Protein Chromophore Analogues Made by Decorating the Imidazolone Ring
- Gutiérrez, Sara. 1
- Martínez-Lõpez, D. 2
- Morõn, M. 1
- Sucunza, D. 1
- Sampedro, D. 2
- Domingo, A. 1
- Salgado, A. 3
- Vaquero, J.J. 1
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1
Universidad de Alcalá
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2
Universidad de La Rioja
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3
Universidad Yachay Tech
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ISSN: 0947-6539
Año de publicación: 2015
Volumen: 21
Número: 51
Páginas: 18758-18763
Tipo: Artículo
Otras publicaciones en: Chemistry - A European Journal
Resumen
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)-1H-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-4H-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-4H-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. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.