A benzothiazole-based fluorescent probe for thiol bioimaging

Sun, Wei; Li, Wenhua; Li, Jing; Zhang, Jian; Du, Lüpei; Li, Minyong

doi:10.1016/j.tetlet.2012.02.098

Cited by 37 publications

(13 citation statements)

References 18 publications

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“…Most probes for the detection of thiols have been developed by exploiting the strong nucleophilicity of the thiols and their affinity for transition metal ions [7,11]. 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]. In recent years, Michael-type probes have been widely developed because thiols react readily with 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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“…reported that 2,4‐dinitrobenzenesulfonyl fluorescein derivatives can act as ON–OFF fluorescent probes toward thiols because of the highly selective aromatic nucleophilic addition of thiols to the highly electron‐deficient aromatic ring 15. These seminal studies allowed the extension of the reactive 2,4‐dinitrobenzenesulfonyl derivatives to new fluorescent compounds, such as cyanine,16 merocyanine,17 boron‐dipyrromethene (BODIPY),18 benzothiazol,19 and coumarin 20. Remarkably, despite the excellent properties of xanthene‐based dyes, the corresponding 2,4‐dinitrobenzenesulfonyl derivatives have not been described to date.…”

Section: Introductionmentioning

confidence: 99%

New Dual Fluorescent Probe for Simultaneous Biothiol and Phosphate Bioimaging

Resa

Orte

Miguel

et al. 2015

Chemistry A European J

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The simultaneous detection of relevant metabolites in living organisms by using one molecule introduces an approach to understanding the relationships between these metabolites in healthy and deregulated cells. Fluorescent probes of low toxicity are remarkable tools for this type of analysis of biological systems in vivo. As a proof of concept, different naturally occurring compounds, such as biothiols and phosphate anions, were the focus for this work. The 2,4-dinitrobenzenesulfinate (DNBS) derivative of 9-[1-(4-tert-butyl-2-methoxyphenyl)]-6-hydroxy-3H-xanthen-3-one (Granada Green; GG) were designed and synthesized. This new sulfinyl xanthene derivative can act as a dual sensor for the aforementioned analytes simultaneously. The mechanism of action of this derivative implies thiolysis of the sulfinyl group of the weakly fluorescent DNBS-GG by biological thiols at near-neutral pH values, thus releasing the fluorescent GG moiety, which simultaneously responds to phosphate anions through its fluorescence-decay time. The new dual probe was tested in solution by using steady-state and time-resolved fluorescence and intracellularly by using fluorescence-lifetime imaging microscopy (FLIM) in human epithelioid cervix carcinoma (HeLa) cells.

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“…Therefore, fluorescent probes that respond to thiols specifically within the lysosome are of particular interest to elucidate organelle functionality. Despite modern achievements with lysosome fluorescent probes, detecting thiols in some special organelles is still very challenging 14 37 38 39 40 41 42 . The traditional one-photon microscopy imaging technique (OPM), that observes the response of the fluorescent probe with thiols, has been favorably substituted with a two-photon microscopy (TPM) due to lower photo-toxicity, improved three dimensional spatial localization, deeper penetration and decreased self-absorption events 43 44 .…”

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confidence: 99%

A Two-Photon Fluorescent Probe for Lysosomal Thiols in Live Cells and Tissues

Fan

Han

Yao

et al. 2016

Sci Rep

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Lysosome-specific fluorescent probes are exclusive to elucidate the functions of lysosomal thiols. Moreover, two-photon microscopy offers advantages of less phototoxicity, better three dimensional spatial localization, deeper penetration depth and lower self-absorption. However, such fluorescent probes for thiols are still rare. In this work, an efficient two-photon fluorophore 1,8-naphthalimide-based probe conjugating a 2,4-dinitrobenzenesulfonyl chloride and morpholine was designed and synthesized, which exhibited high selectivity and sensitivity towards lysosomal thiols by turn-on fluorescence method quantitatively and was successfully applied to the imaging of thiols in live cells and tissues by two-photon microscopy.

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A benzothiazole-based fluorescent probe for thiol bioimaging

Cited by 37 publications

References 18 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

New Dual Fluorescent Probe for Simultaneous Biothiol and Phosphate Bioimaging

A Two-Photon Fluorescent Probe for Lysosomal Thiols in Live Cells and Tissues

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