Journal
DYES AND PIGMENTS
Volume 93, Issue 1-3, Pages 1447-1455Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2011.10.010
Keywords
Catechol; Fluorescein; Chemosensor; Fluorescence spectroscopy; Iron(III); Microwave irradiation
Funding
- Fundacao para a Ciencia e aTecnologia (FCT) [PEst-C/EQB/LA0006/2011, PTDC/QUI/67915/2006, SFRH/BPD/34262/2006]
- POCI (FEDER) [REDE/1517/RMN/2005]
- Fundação para a Ciência e a Tecnologia [PTDC/QUI/67915/2006] Funding Source: FCT
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In the present work we report the synthesis and characterization of a novel fluorescein-based dye containing a catechol chelating unit designed to act as a chemosensor for iron(III). The compound was prepared using conventional and microwave-assisted amide coupling of a catechol derivative with a 5(6)-carboxyfluorescein scaffold. One of the most interesting features of this conjugate structure is a high affinity binding site on the catechol ring close to the fluorophore. As a consequence, the behaviour of the new compound in the presence of metal ions of biological importance was monitored by optical spectroscopy (at physiological pH). The results show that the conjugate is particularly sensitive to iron(III), thus suggesting that it may be used as fluorescent chemosensor for the detection of iron(III) in cellular systems. (C) 2011 Elsevier Ltd. All rights reserved.
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