title: Highly Fluorescent Green Fluorescent Protein Chromophore Analogues Made by Decorating the Imidazolone Ring.
abstract: 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.
authors.affiliation: Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, Edificio de Farmacia, 28871, Alcalá de Henares, Madrid (Spain).
authors.forename: Sara
authors.initials: S
authors.lastname: Gutiérrez
authors.affiliation: Departamento de Química, Centro de Investigación en Síntesis Química (CISQ), Universidad de La Rioja, Madre de Dios, 53, 26006, Logroño, La Rioja (Spain).
authors.forename: David
authors.initials: D
authors.lastname: Martínez-López
authors.affiliation: Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, Edificio de Farmacia, 28871, Alcalá de Henares, Madrid (Spain).
authors.forename: María
authors.initials: M
authors.lastname: Morón
authors.affiliation: Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, Edificio de Farmacia, 28871, Alcalá de Henares, Madrid (Spain). david.sucunza@uah.es.
authors.forename: David
authors.initials: D
authors.lastname: Sucunza
authors.affiliation: Departamento de Química, Centro de Investigación en Síntesis Química (CISQ), Universidad de La Rioja, Madre de Dios, 53, 26006, Logroño, La Rioja (Spain). diego.sampedro@unirioja.es.
authors.forename: Diego
authors.initials: D
authors.lastname: Sampedro
authors.affiliation: Departamento de Biología de Sistemas, Universidad de Alcalá, Edificio de Medicina, 28871, Alcalá de Henares, Madrid (Spain).
authors.forename: Alberto
authors.initials: A
authors.lastname: Domingo
authors.affiliation: Departamento de Química, Universidad Yachay Tech, Hacienda San José s/n, San Miguel de Urcuquí, 100119 (Ecuador).
authors.forename: Antonio
authors.initials: A
authors.lastname: Salgado
authors.affiliation: Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, Edificio de Farmacia, 28871, Alcalá de Henares, Madrid (Spain). juanjose.vaquero@uah.es.
authors.forename: Juan J
authors.initials: JJ
authors.lastname: Vaquero
mesh_terms: D001597:Benzylidene Compounds / Q000737:chemistry*; D049452:Green Fluorescent Proteins / Q000737:chemistry* / Q000378:metabolism; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000737:chemistry*; D011437:Propylamines / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
chemical_list: C000608186:4-(4-hydroxybenzylidene)-1-propyl-2-(propylamino)-1H-imidazol-5(4 H)-one; C000608188:5-(4-hydroxybenzylidene)-2,3-dimethyl-3,5-dihydro-4H-imidazol-4-one; D001597:Benzylidene Compounds; D007093:Imidazoles; D011437:Propylamines; C117197:imidazolone; D049452:Green Fluorescent Proteins
keywords: TD-DFT calculations; cell staining; fluorescence; imidazolone derivatives; proteins