Highly Fluorescent Green Fluorescent Protein Chromophore Analogues Made by Decorating the Imidazolone Ring

  1. Gutiérrez, Sara. 1
  2. Martínez-Lõpez, D. 2
  3. Morõn, M. 1
  4. Sucunza, D. 1
  5. Sampedro, D. 2
  6. Domingo, A. 1
  7. Salgado, A. 3
  8. Vaquero, J.J. 1
  1. 1 Universidad de Alcalá
    info

    Universidad de Alcalá

    Alcalá de Henares, España

    ROR https://ror.org/04pmn0e78

  2. 2 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  3. 3 Universidad Yachay Tech
    info

    Universidad Yachay Tech

    Urcuquí, Ecuador

    ROR https://ror.org/04jjswc10

Revista:
Chemistry - A European Journal

ISSN: 0947-6539

Año de publicación: 2015

Volumen: 21

Número: 51

Páginas: 18758-18763

Tipo: Artículo

DOI: 10.1002/CHEM.201502929 SCOPUS: 2-s2.0-84955192282 WoS: WOS:000368280400038 GOOGLE SCHOLAR

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.