The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study

García‐Beltrán, Olimpo; Mena, Natalia; Pérez, Edwin G.; Cassels, Bruce K.; Núñez, Marco T.; Werlinger, Francisca; Zavala, Daniel; Aliaga, Margarita E.; Pavez, Paulina

doi:10.1016/j.tetlet.2011.09.137

Cited by 28 publications

(24 citation statements)

References 19 publications

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“…Accordingly, the optical detection of cysteine derivatives is based on specific reactions between the probes and thiols [12], such as nucleophilic addition [9,[13][14][15][16], nucleophilic substitution [8], cyclisation with an aldehyde [17], a cleavage reaction by thiols [18][19][20], oxidation-reduction of metal complexes [21], and others [7,10,20,22,23]. Maleimide moieties [10,24], a,b-unsaturated aldehydes [25], ketones [26], esters [27], and malononitriles [13] have been utilised as excellent Michael acceptors. Maleimide moieties [10,24], a,b-unsaturated aldehydes [25], ketones [26], esters [27], and malononitriles [13] have been utilised as excellent Michael acceptors.…”

Section: Introductionmentioning

confidence: 99%

Dyes derived from 3‐formyl‐2(1H)‐quinolone – synthesis, spectroscopic characterisation, and their behaviour in the presence of sulfhydryl and non‐sulfhydryl amino acids

Kowalska

Kolińska

Sokołowska

2015

Coloration Technology

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Novel dyes based on a 3-formyl-2(1H)-quinolone skeleton were synthesised and characterised using 1 H nuclear magnetic resonance spectroscopy and mass spectrometry. The spectroscopic properties of these dyes, such as their absorption spectra, emission spectra, and quantum fluorescence yields, were also examined. The behaviour of the obtained compounds at a pH of 7.4 in the absence and in the presence of thiol amino acids, such as L-cysteine, L-glutathione, and N-acetyl-L-cysteine, were studied. The spectroscopic responses of the tested dyes towards other amino acids were also investigated. A reference compound was synthesised to understand the reaction mechanism between the thiols and the obtained dyes. The experimental results show that the synthesised dyes have the potential to act as sensors for thiols. Coloration TechnologySociety of Dyers and Colourists 157

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Section: Introductionmentioning

confidence: 99%

Dyes derived from 3‐formyl‐2(1H)‐quinolone – synthesis, spectroscopic characterisation, and their behaviour in the presence of sulfhydryl and non‐sulfhydryl amino acids

Kowalska

Kolińska

Sokołowska

2015

Coloration Technology

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“…These are often colorimetric and fluorescent probes. In the past decade, much effort has been devoted to the development of different probes based on Michael addition, derived from fluorescein , coumarin , squarane , croconium , naphthopyranone , BODIPY , and others .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, spectroscopic characterisation, and potential application of dyes containing a carbostyril skeleton as sensors for thiols

2015

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Several dyes based on a carbostyril skeleton were synthesised and characterised using proton nuclear magnetic resonance spectroscopy and electron ionisation mass spectrometry. Their basic spectroscopic properties, such as absorption and emission spectra, were also measured. The behaviour of the obtained dyes in the absence and presence of thiol amino acids and other compounds under various conditions were studied. These dyes contain various moieties in the structure, acting as Michael acceptors. Results show that the studied compounds have the potential to act as colorimetric sensors for thiols, but the benzothioazolium dyes are less effective than dicyanoethylene derivatives.

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“…Reactions of L 1 and L 2 with different amino acids, cystine, glucose, DNA, and hydroxy/mercapto ethylamines, and their selective optical responses : In general, a problem associated with most literature procedures for the direct detection of Cys/Hcy is interference in the detection process by structurally related molecules, such as thiol‐bearing peptides, glutathione (GSH), other amino acids, 2‐mercaptoethanol, and hydroxy/mercapto ethylamines 14l. 15c, 16e In order to evaluate the recognition specificity of the two chemodosimetric reagents L 1 and L 2 towards Cys/Hcy, we extended our studies to other amino acids, cystine, glucose, CT‐DNA, ethanolamine (NH 2 CH 2 CH 2 OH), cysteamine (NH 2 CH 2 CH 2 SH), and 2‐mercaptoethanol (SHCH 2 CH 2 OH) in an appropriate DMSO/aqueous HEPES buffer medium of pH 7.4 at room temperature.…”

Section: Resultsmentioning

confidence: 99%

New Chemodosimetric Reagents as Ratiometric Probes for Cysteine and Homocysteine and Possible Detection in Living Cells and in Blood Plasma

Das

Mandal

Chandar

et al. 2012

Chemistry A European J

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In this work, we have rationally designed and synthesized two new reagents (L(1) and L(2)), each bearing a pendant aldehyde functionality. This aldehyde group can take part in cyclization reactions with β- or γ-amino thiols to yield the corresponding thiazolidine and thiazinane derivatives, respectively. The intramolecular charge-transfer (ICT) bands of these thiazolidine and thiazinane derivatives are distinctly different from those of the molecular probes (L(1) and L(2)). Such changes could serve as a potential platform for using L(1) and L(2) as new colorimetric/fluorogenic as well as ratiometric sensors for cysteine (Cys) and homocysteine (Hcy) under physiological conditions. Both reagents proved to be specific towards Cys and Hcy even in the presence of various amino acids, glucose, and DNA. Importantly, these two chemodosimetric reagents could be used for the quantitative detection of Cys present in blood plasma by using a pre-column HPLC technique. Such examples are not common in contemporary literature. MTT assay studies have revealed that these probes have low cytotoxicity. Confocal laser scanning micrographs of cells demonstrated that these probes could penetrate cell membranes and could be used to detect intracellular Cys/Hcy present within living cells. Thus, the results presented in this article not only demonstrate the efficiency and specificity of two ratiometric chemodosimeter molecules for the quantitative detection of Cys and Hcy, but also provide a strategy for developing reagents for analysis of these vital amino acids in biological samples.

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The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study

Cited by 28 publications

References 19 publications

Dyes derived from 3‐formyl‐2(1H)‐quinolone – synthesis, spectroscopic characterisation, and their behaviour in the presence of sulfhydryl and non‐sulfhydryl amino acids

Dyes derived from 3‐formyl‐2(1H)‐quinolone – synthesis, spectroscopic characterisation, and their behaviour in the presence of sulfhydryl and non‐sulfhydryl amino acids

Synthesis, spectroscopic characterisation, and potential application of dyes containing a carbostyril skeleton as sensors for thiols

New Chemodosimetric Reagents as Ratiometric Probes for Cysteine and Homocysteine and Possible Detection in Living Cells and in Blood Plasma

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