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.
%0 Journal Article
%1 RN194
%A Garcia-Beltran, O.
%A Cassels, B.K.
%A Perez, C.
%A Mena, N.
%A Nunez, M.T.
%A Martinez, N.P.
%A Pavez, P.
%A Aliaga, M.E.
%D 2014
%J Sensors
%K bio-imaging, chemosensor, coumarin-based cu2+ cu2+, design, dqcauchile fe3+ fluorescence ion, probes, sensor sensors, turn-off
%N 1
%P 1358-1371
%R 10.3390/s140101358
%T Coumarin-Based Fluorescent Probes for Dual Recognition of Copper(Ii) and Iron(Iii) Ions and Their Application in Bio-Imaging
%U /brokenurl#<Go to ISI>://WOS:000336039100075
%V 14
%X 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.
@article{RN194,
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.},
added-at = {2019-12-04T03:57:35.000+0100},
author = {Garcia-Beltran, O. and Cassels, B.K. and Perez, C. and Mena, N. and Nunez, M.T. and Martinez, N.P. and Pavez, P. and Aliaga, M.E.},
biburl = {https://www.bibsonomy.org/bibtex/20ae0c5dea461ad258ca595d9b1f0daa9/dqcauchile},
doi = {10.3390/s140101358},
interhash = {b0517b009a0919d9b83776aae962e064},
intrahash = {0ae0c5dea461ad258ca595d9b1f0daa9},
issn = {1424-8220},
journal = {Sensors},
keywords = {bio-imaging, chemosensor, coumarin-based cu2+ cu2+, design, dqcauchile fe3+ fluorescence ion, probes, sensor sensors, turn-off},
number = 1,
pages = {1358-1371},
timestamp = {2019-12-04T03:58:17.000+0100},
title = {Coumarin-Based Fluorescent Probes for Dual Recognition of Copper(Ii) and Iron(Iii) Ions and Their Application in Bio-Imaging},
type = {Journal Article},
url = {/brokenurl#<Go to ISI>://WOS:000336039100075},
volume = 14,
year = 2014
}