Abstract
A new green-emitting fluorescent probe 1 was developed for biothiol detection. The sensing mechanism was considered to be biothiol-induced cleavage of the 2,4-dinitrobenzene- sulfonate group in probe 1 and resulting inhibition of the probe’s photoinduced electron transfer (PET) process. Probe 1 exhibited favorable properties such as excellent selectivity, highly sensitive (0.12 µM), large Stokes shift (117 nm) and a remarkable turn-on fluorescence signal (148-fold). Furthermore, confocal fluorescence imaging indicated that probe 1 was membrane-permeable and suitable for visualization of biothiols in living A549 cells.
Highlights
Biological thiols play essential functions in many physiological processes of prokaryotes and eukaryotes owing to their redox-relevant role and nucleophilicity [1–3]
Cysteine (Cys), homocysteine (Hcy) and glutathione are the most plentiful low molecular weight and typical endogenous biothiols [4–6]. Their content is of critical significance, and the abnormal levels of biothiols are directly linked with the occurence of some diseases
We firstly evaluated the sensing capability of probe 1 to detect biothiols in PBS buffer solution (50.0 mM, pH 7.4, 20% DMSO)
Summary
Biological thiols (biothiols) play essential functions in many physiological processes of prokaryotes and eukaryotes owing to their redox-relevant role and nucleophilicity [1–3]. Cysteine (Cys), homocysteine (Hcy) and glutathione are the most plentiful low molecular weight and typical endogenous biothiols [4–6]. Their content is of critical significance, and the abnormal levels of biothiols are directly linked with the occurence of some diseases. These studies have greatly advanced the research on the fluorescent detection of thiols [24–38] Many of these probes show low sensitivity and small Stokes shifts, which limits their. We identified the 2,4-dinitrobenzenesulfonate moiety (DNBS) as a reactive group and reaction switch specific for biothiols Integration of this unique moiety into the phenothiazine benzothiazole-based dye 2 fluorophore afforded a new turn-on fluorescence probe 1 for detection of biothiols (Scheme 1).
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