Quantum chemical elucidation of the turn-on luminescence mechanism in two new Schiff bases as selective chemosensors of Zn2+: Synthesis, theory and bioimaging applications

Jessica C. Berrones-Reyes, Blanca M. Muñoz-Flores, Arelly M. Cantón-Diáz, Manuel A. Treto-Suárez, Dayan Páez-Hernández, Eduardo Schott, Ximena Zarate, Víctor M. Jiménez-Pérez

Resultado de la investigación: Article

Resumen

We report the synthesis and characterization of two new selective zinc sensors (S,E)-11-amino-8-((2,4-di-tert-butyl-1-hydroxybenzylidene) amino)-11-oxopentanoic acid (A) and (S,E)-11-amino-8-((8-hydroxybenzylidene)amino)-11-oxopentanoic acid (B) based on a Schiff base and an amino acid. The fluorescent probes, after binding to Zn2+ ions, presented an enhancement in fluorescent emission intensity up to 30 times (ϕ = A 50.10 and B 18.14%). The estimated LOD for compounds A and B was 1.17 and 1.20 μM respectively (mixture of acetonitrile : water 1 : 1). Theoretical research has enabled us to rationalize the behaviours of the two selective sensors to Zn2+ synthesized in this work. Our results showed that in the free sensors, PET and ESIPT are responsible for the quenching of the luminescence and that the turn-on of luminescence upon coordination to Zn2+ is mainly induced by the elimination of the PET, which is deeply analysed through EDA, NOCV, molecular structures, excited states and electronic transitions via TD-DFT computations. Confocal fluorescence microscopy experiments demonstrate that compound A could be used as a fluorescent probe for Zn2+ in living cells.

Idioma originalEnglish
Páginas (desde-hasta)30778-30789
Número de páginas12
PublicaciónRSC Advances
Volumen9
N.º53
DOI
EstadoPublished - 1 ene 2019

Huella dactilar

Schiff Bases
Luminescence
Sensors
Fluorescent Dyes
Acids
Confocal microscopy
Fluorescence microscopy
Electron transitions
Acetonitrile
Excited states
Discrete Fourier transforms
Molecular structure
Amino acids
Zinc
Quenching
Cells
Ions
Amino Acids
Water
Experiments

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Citar esto

Berrones-Reyes, J. C., Muñoz-Flores, B. M., Cantón-Diáz, A. M., Treto-Suárez, M. A., Páez-Hernández, D., Schott, E., ... Jiménez-Pérez, V. M. (2019). Quantum chemical elucidation of the turn-on luminescence mechanism in two new Schiff bases as selective chemosensors of Zn2+: Synthesis, theory and bioimaging applications. RSC Advances, 9(53), 30778-30789. https://doi.org/10.1039/c9ra05010h
Berrones-Reyes, Jessica C. ; Muñoz-Flores, Blanca M. ; Cantón-Diáz, Arelly M. ; Treto-Suárez, Manuel A. ; Páez-Hernández, Dayan ; Schott, Eduardo ; Zarate, Ximena ; Jiménez-Pérez, Víctor M. / Quantum chemical elucidation of the turn-on luminescence mechanism in two new Schiff bases as selective chemosensors of Zn2+ : Synthesis, theory and bioimaging applications. En: RSC Advances. 2019 ; Vol. 9, N.º 53. pp. 30778-30789.
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title = "Quantum chemical elucidation of the turn-on luminescence mechanism in two new Schiff bases as selective chemosensors of Zn2+: Synthesis, theory and bioimaging applications",
abstract = "We report the synthesis and characterization of two new selective zinc sensors (S,E)-11-amino-8-((2,4-di-tert-butyl-1-hydroxybenzylidene) amino)-11-oxopentanoic acid (A) and (S,E)-11-amino-8-((8-hydroxybenzylidene)amino)-11-oxopentanoic acid (B) based on a Schiff base and an amino acid. The fluorescent probes, after binding to Zn2+ ions, presented an enhancement in fluorescent emission intensity up to 30 times (ϕ = A 50.10 and B 18.14{\%}). The estimated LOD for compounds A and B was 1.17 and 1.20 μM respectively (mixture of acetonitrile : water 1 : 1). Theoretical research has enabled us to rationalize the behaviours of the two selective sensors to Zn2+ synthesized in this work. Our results showed that in the free sensors, PET and ESIPT are responsible for the quenching of the luminescence and that the turn-on of luminescence upon coordination to Zn2+ is mainly induced by the elimination of the PET, which is deeply analysed through EDA, NOCV, molecular structures, excited states and electronic transitions via TD-DFT computations. Confocal fluorescence microscopy experiments demonstrate that compound A could be used as a fluorescent probe for Zn2+ in living cells.",
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Berrones-Reyes, JC, Muñoz-Flores, BM, Cantón-Diáz, AM, Treto-Suárez, MA, Páez-Hernández, D, Schott, E, Zarate, X & Jiménez-Pérez, VM 2019, 'Quantum chemical elucidation of the turn-on luminescence mechanism in two new Schiff bases as selective chemosensors of Zn2+: Synthesis, theory and bioimaging applications', RSC Advances, vol. 9, n.º 53, pp. 30778-30789. https://doi.org/10.1039/c9ra05010h

Quantum chemical elucidation of the turn-on luminescence mechanism in two new Schiff bases as selective chemosensors of Zn2+ : Synthesis, theory and bioimaging applications. / Berrones-Reyes, Jessica C.; Muñoz-Flores, Blanca M.; Cantón-Diáz, Arelly M.; Treto-Suárez, Manuel A.; Páez-Hernández, Dayan; Schott, Eduardo; Zarate, Ximena; Jiménez-Pérez, Víctor M.

En: RSC Advances, Vol. 9, N.º 53, 01.01.2019, p. 30778-30789.

Resultado de la investigación: Article

TY - JOUR

T1 - Quantum chemical elucidation of the turn-on luminescence mechanism in two new Schiff bases as selective chemosensors of Zn2+

T2 - Synthesis, theory and bioimaging applications

AU - Berrones-Reyes, Jessica C.

AU - Muñoz-Flores, Blanca M.

AU - Cantón-Diáz, Arelly M.

AU - Treto-Suárez, Manuel A.

AU - Páez-Hernández, Dayan

AU - Schott, Eduardo

AU - Zarate, Ximena

AU - Jiménez-Pérez, Víctor M.

PY - 2019/1/1

Y1 - 2019/1/1

N2 - We report the synthesis and characterization of two new selective zinc sensors (S,E)-11-amino-8-((2,4-di-tert-butyl-1-hydroxybenzylidene) amino)-11-oxopentanoic acid (A) and (S,E)-11-amino-8-((8-hydroxybenzylidene)amino)-11-oxopentanoic acid (B) based on a Schiff base and an amino acid. The fluorescent probes, after binding to Zn2+ ions, presented an enhancement in fluorescent emission intensity up to 30 times (ϕ = A 50.10 and B 18.14%). The estimated LOD for compounds A and B was 1.17 and 1.20 μM respectively (mixture of acetonitrile : water 1 : 1). Theoretical research has enabled us to rationalize the behaviours of the two selective sensors to Zn2+ synthesized in this work. Our results showed that in the free sensors, PET and ESIPT are responsible for the quenching of the luminescence and that the turn-on of luminescence upon coordination to Zn2+ is mainly induced by the elimination of the PET, which is deeply analysed through EDA, NOCV, molecular structures, excited states and electronic transitions via TD-DFT computations. Confocal fluorescence microscopy experiments demonstrate that compound A could be used as a fluorescent probe for Zn2+ in living cells.

AB - We report the synthesis and characterization of two new selective zinc sensors (S,E)-11-amino-8-((2,4-di-tert-butyl-1-hydroxybenzylidene) amino)-11-oxopentanoic acid (A) and (S,E)-11-amino-8-((8-hydroxybenzylidene)amino)-11-oxopentanoic acid (B) based on a Schiff base and an amino acid. The fluorescent probes, after binding to Zn2+ ions, presented an enhancement in fluorescent emission intensity up to 30 times (ϕ = A 50.10 and B 18.14%). The estimated LOD for compounds A and B was 1.17 and 1.20 μM respectively (mixture of acetonitrile : water 1 : 1). Theoretical research has enabled us to rationalize the behaviours of the two selective sensors to Zn2+ synthesized in this work. Our results showed that in the free sensors, PET and ESIPT are responsible for the quenching of the luminescence and that the turn-on of luminescence upon coordination to Zn2+ is mainly induced by the elimination of the PET, which is deeply analysed through EDA, NOCV, molecular structures, excited states and electronic transitions via TD-DFT computations. Confocal fluorescence microscopy experiments demonstrate that compound A could be used as a fluorescent probe for Zn2+ in living cells.

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DO - 10.1039/c9ra05010h

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JO - RSC Advances

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