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

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.

A novel system for Fe3+ ion detection based on fluorescence resonance energy transfer

“…The detection limit of Fe 3+ was determined to be 2.54 M using the 3s/k equation. Compared to recent studies regarding this value, it has been reached a very low detection limit of Fe 3+ ion [24,30,31]. Moreover, according to the U.S. Environmental Protection Agency (EPA), the maximum Fe 3+ levels in drinking water must be ∼5.357 M [32].…”

Thiophene aldehyde-diamino uracil Schiff base: A novel fluorescent probe for detection and quantification of cupric, silver and ferric ions

“…Encouraged by these considerations, we developed DDUTS as a novel fluorescence probe for Ag + , Cu 2+ and Fe 3+ ions in aqueous solutions. Reports on fluorescent sensors for more than one metal ions are rare and is known for a few combination of metal ions, like Cu 2+ , Ni 2+ [52]; Zn 2+ , Ni 2+ [53,54]; Cu 2+ , Zn 2+ [55]; Cu 2+ , Hg 2+ [31]; Cu 2+ , Fe 3+ [26]; Mg 2+ , Zn 2+ [56]; Ag + , Zn 2+ [16]; Ni 2+ , Fe 3+ [45]; Hg 2+ , Ag + [11,57]; F À , Cu 2+ [58]; Pb 2+ , K + [59] and Pb 2+ , Al 3+ [60]. To the best of our knowledge, fluorescence sensing for ternary cation samples is still lacking in the literature, which shows the importance of the developed fluorescent sensor in both detection and quantification of Ag + , Cu 2+ and Fe 3+ ions.…”

“…Copper ion fluorescent sensors include heptamethine cyanine-based near-infrared fluorescent probe [17], dansyl-based probe [18], 6-(N,N-dimethylamino)-2-naphthoylacryl acid [19], triarylpyrazoline-based Cu(I) sensor [20], coumarin Schiff base [21], near-infrared fluorescent probe based on photo-induced electron transfer mechanism [22], bis-benzimidazolyldiamide-based probe [23], riboflavin-stabilized gold nanoclusters [24], [3-diam inophenazine, 1,2-diamino-anthraquinone and 2,4-dinitrophen ylhydrazine] [25], coumarin-based sensor [26,27], dehydroabietyl derivative bearing a 2-(2 0 -hydroxyphenyl) benzimidazole unit [28], rhodamine B hydrazide hydrazone derivative [29], carboxylic acid-functionalized tris(2,2 0 -bipyridine)-ruthenium(II) complex [30], thiourea-based probe [31], carbazole-based Schiff base [32], rhodamine-based probe [33], silver nanoclusters (Ag NCs) [34], 1,8-diaminonaphthalene-based sensor [35] and malonamide fluoroionophore [36].…”

“…Ferric ion fluorescent sensors include carbogenic nanoparticles (NPs) [37], naphthalimide-based probe [38], Europium metal with chelating terpyridine sites [39], pyoverdin [40], FITC/Au 1 Ag 4 @SiO 2 nanoparticles [41], 2-(-4-aminophenyl)-benzothiazole and 2-picolylamine derivatives [42], N-phenyl-2-(2-hydroxynap hthale n-1-ylmethylene)hydrazinecarbothioamide [43], coumarin or fluorescein and 3-hydroxy-pyridin-4-one or 3-hydroxy-pyran-4-one [44], perylenetetracarboxylicdiimide [45], calcein [46], coumarin-based probe [26], rhodamine-based sensor [47] and deprotection of acetal reaction [48].…”

Thiazolothiazole‐Based Fluorescence Probe towards Detection of Copper and Iron Ions through Formation of Radical Cations

“…Fe 3+ metal ion was detected via fluorescent quenching and Cu 2+ was detected via colorimetry (colourless to pink). García‐Beltrán et al . have demonstrated coumarin‐based fluorescent probes for detecting Cu 2+ and Fe 3+ metal ions through fluorescent turn‐off method and their detection limit for Cu 2+ and Fe 3+ were 8.5 μM and 2.0 μM, respectively.…”