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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 (CC BY 3.0).

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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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