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Sensors 2014, 14(1), 1358-1371; doi:10.3390/s140101358
Article

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

1,2,* , 1
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1
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3
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3
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4
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4
 and
4,*
1 Department of Chemistry, Faculty of Sciences, University of Chile, Santiago 7800024, Chile 2 Facultad de Ciencias Naturales y Matemáticas, Universidad de Ibagué, Carrera 22 Calle 67, Ibagué 730001, Colombia 3 Department of Biology, Faculty of Sciences, University of Chile, Santiago 7800024, Chile 4 Facultad de Química, Pontificia Universidad Católica de Chile, Casilla 306, Santiago 6094411, Chile
* Authors to whom correspondence should be addressed.
Received: 31 October 2013 / Revised: 18 December 2013 / Accepted: 18 December 2013 / Published: 13 January 2014
(This article belongs to the Special Issue Fluorescent Biosensors)
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Abstract

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 Cu2+ and Fe3+ 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 Cu2+ and Fe3+ ions can be imaged in human neuroblastoma SH-SY5Y cells treated with the tested probes.
Keywords: Cu2+ ion; Fe3+ ion; turn-off probes; coumarin-based probes; fluorescence sensors; bio-imaging Cu2+ ion; Fe3+ ion; turn-off probes; coumarin-based probes; fluorescence sensors; bio-imaging
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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García-Beltrán, O.; Cassels, B.K.; Pérez, C.; Mena, N.; Núñez, M.T.; Martínez, N.P.; Pavez, P.; Aliaga, M.E. Coumarin-Based Fluorescent Probes for Dual Recognition of Copper(II) and Iron(III) Ions and Their Application in Bio-Imaging. Sensors 2014, 14, 1358-1371.

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