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Coumarin-Based Fluorescent Probes for Dual Recognition of Copper(II) and Iron(III) Ions and Their Application in Bio-Imaging

Two new coumarin-based “turn-off” fluorescent probes, (E)-3-((3,4-dihydroxybenzylidene)amino)-7-hydroxy-2H-chromen-2-one (BS1) and (E)-3-((2,4-dihydroxybenzylidene)amino)-7-hydroxy-2H-chromen-2-one (BS2), were synthesized and their detection of copper(II) and iron(III) ions was studied. Results show...

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Autores principales: García-Beltrán, Olimpo, Cassels, Bruce K., Pérez, Claudio, Mena, Natalia, Núñez, Marco T., Martínez, Natalia P., Pavez, Paulina, Aliaga, Margarita E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International (MDPI) 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3926618/
https://www.ncbi.nlm.nih.gov/pubmed/24419164
http://dx.doi.org/10.3390/s140101358
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author García-Beltrán, Olimpo
Cassels, Bruce K.
Pérez, Claudio
Mena, Natalia
Núñez, Marco T.
Martínez, Natalia P.
Pavez, Paulina
Aliaga, Margarita E.
author_facet García-Beltrán, Olimpo
Cassels, Bruce K.
Pérez, Claudio
Mena, Natalia
Núñez, Marco T.
Martínez, Natalia P.
Pavez, Paulina
Aliaga, Margarita E.
author_sort García-Beltrán, Olimpo
collection PubMed
description Two new coumarin-based “turn-off” fluorescent probes, (E)-3-((3,4-dihydroxybenzylidene)amino)-7-hydroxy-2H-chromen-2-one (BS1) and (E)-3-((2,4-dihydroxybenzylidene)amino)-7-hydroxy-2H-chromen-2-one (BS2), were synthesized and their detection of copper(II) and iron(III) ions was studied. Results show that both compounds are highly selective for Cu(2+) and Fe(3+) ions over other metal ions. However, BS2 is detected directly, while detection of BS1 involves a hydrolysis reaction to regenerate 3-amino-7-hydroxycoumarin (3) and 3,4-dihydroxybenzaldehyde, of which 3 is able to react with copper(II) or iron(III) ions. The interaction between the tested compounds and copper or iron ions is associated with a large fluorescence decrease, showing detection limits of ca. 10(−5) M. Preliminary studies employing epifluorescence microscopy demonstrate that Cu(2+) and Fe(3+) ions can be imaged in human neuroblastoma SH-SY5Y cells treated with the tested probes.
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spelling pubmed-39266182014-02-18 Coumarin-Based Fluorescent Probes for Dual Recognition of Copper(II) and Iron(III) Ions and Their Application in Bio-Imaging García-Beltrán, Olimpo Cassels, Bruce K. Pérez, Claudio Mena, Natalia Núñez, Marco T. Martínez, Natalia P. Pavez, Paulina Aliaga, Margarita E. Sensors (Basel) Article Two new coumarin-based “turn-off” fluorescent probes, (E)-3-((3,4-dihydroxybenzylidene)amino)-7-hydroxy-2H-chromen-2-one (BS1) and (E)-3-((2,4-dihydroxybenzylidene)amino)-7-hydroxy-2H-chromen-2-one (BS2), were synthesized and their detection of copper(II) and iron(III) ions was studied. Results show that both compounds are highly selective for Cu(2+) and Fe(3+) ions over other metal ions. However, BS2 is detected directly, while detection of BS1 involves a hydrolysis reaction to regenerate 3-amino-7-hydroxycoumarin (3) and 3,4-dihydroxybenzaldehyde, of which 3 is able to react with copper(II) or iron(III) ions. The interaction between the tested compounds and copper or iron ions is associated with a large fluorescence decrease, showing detection limits of ca. 10(−5) M. Preliminary studies employing epifluorescence microscopy demonstrate that Cu(2+) and Fe(3+) ions can be imaged in human neuroblastoma SH-SY5Y cells treated with the tested probes. Molecular Diversity Preservation International (MDPI) 2014-01-13 /pmc/articles/PMC3926618/ /pubmed/24419164 http://dx.doi.org/10.3390/s140101358 Text en © 2014 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
García-Beltrán, Olimpo
Cassels, Bruce K.
Pérez, Claudio
Mena, Natalia
Núñez, Marco T.
Martínez, Natalia P.
Pavez, Paulina
Aliaga, Margarita E.
Coumarin-Based Fluorescent Probes for Dual Recognition of Copper(II) and Iron(III) Ions and Their Application in Bio-Imaging
title Coumarin-Based Fluorescent Probes for Dual Recognition of Copper(II) and Iron(III) Ions and Their Application in Bio-Imaging
title_full Coumarin-Based Fluorescent Probes for Dual Recognition of Copper(II) and Iron(III) Ions and Their Application in Bio-Imaging
title_fullStr Coumarin-Based Fluorescent Probes for Dual Recognition of Copper(II) and Iron(III) Ions and Their Application in Bio-Imaging
title_full_unstemmed Coumarin-Based Fluorescent Probes for Dual Recognition of Copper(II) and Iron(III) Ions and Their Application in Bio-Imaging
title_short Coumarin-Based Fluorescent Probes for Dual Recognition of Copper(II) and Iron(III) Ions and Their Application in Bio-Imaging
title_sort coumarin-based fluorescent probes for dual recognition of copper(ii) and iron(iii) ions and their application in bio-imaging
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3926618/
https://www.ncbi.nlm.nih.gov/pubmed/24419164
http://dx.doi.org/10.3390/s140101358
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