Probe For Detection Of Thiophenols Research Articles

A novel near-infrared xanthene-based fluorescent probe for detection of thiophenolin vitroandin vivo

A novel near-infrared xanthene-based fluorescent probe for detection of thiophenol in living cells and mice.

Ultrafast 2,7-Naphthyridine-Based fluorescent probe for detection of thiophenol with a remarkable Stokes shift and its application In vitro and in vivo

2,7-Naphthyridine derivatives were developed as fluorophores for the first time to design two fluorescence probes, AND-DNP and ND-DNP, which can be applied for detecting thiophenol in aqueous media. Comparing with ND-DNP, AND-DNP showed more favorable properties such as lower background, larger Stokes shift, and higher fluorescence quantum yield for detecting thiophenol. Moreover, the experimental results were verified by theoretical calculations. Hence, AND-DNP was selected as the superior fluorescence probe to detect thiophenol because of its high sensitivity and selectivity. Based on the experimental results, AND-DNP showed a remarkably larger Stokes shift (225 nm), faster response speed (30 s) and higher fluorescence enhancement (240-fold) than most other fluorescent probes for thiophenol reported in the literature. For an extended application, AND-DNP was applied to detect thiophenol quantitatively in real water samples. Meanwhile, AND-DNP also detected thiophenol via red emission in living A549 cells and zebrafish. All these results proved AND-DNP's potential value as an accurate probe for imaging thiophenol in different environments.

Highly sensitive fluorescent probe based on a novel phenothiazine dye for detection of thiophenols in real water samples and living cells.

Based on an excited-state intramolecular proton transfer (ESIPT) fluorophore, a novel fluorescent off-on probe for detection of thiophenols was designed and synthesized. This probe (λex = 401nm, λem = 527nm) displayed high specificity for sensing thiophenols over other biologically related species. Besides, this probe possessed capabilities of monitoring thiophenols with rapid response rate (3min), a large Stokes shift (126nm), and high sensitivity (2.7nM). The sensing mechanism was considered to be that thiophenols triggered thiolysis of the probe and the ESIPT fluorophore was released, as confirmed by means of HPLC and HRMS. Most notably, this probe was successfully applied to monitor levels of thiophenols in realistic samples and MDA-MB-231 cells. Graphical abstract A novel phenothiazine-based fluorescent probe was developed for sensitively sensing thiophenols in both aqueous medium and living cells.

Iridium (III) complex-based fluorescent probe for detection of thiophenols and its application in water samples

In consideration of the nucleophilic capacity of thiophenols, which could cleave sulfonamide bond under neutral conditions, a cyclometalated iridium(III) complex (probe 1) comprised 2,4-dinitrobenzenesulfonamide (DNBS) as the recognition unit was designed and synthesized to high selectivity and sensitivity detect thiophenols successfully based on internal charge transfer (ICT) mechanism. Upon addition with thiophenols to 20% DMSO/PBS solution of nearly non-fluorescent probe 1 (10 μM, pH = 7.4), fluorescent product (complex 2) was formed after cleavage of DNBS group and a significant emission enhancement at 470 nm was observed. In addition, it could be successfully applied to detect thiophenol in water samples with a high recovery, confirming its practical value in environment science.

A novel isophorone-based red-emitting/NIR probe for thiophenol and its application in real water sample and vivo.

Fast, highly selective and sensitive thiophenol probes are highly desirable in the field of bioimaging and environmental monitoring. For that, based on the mechanism that thiophenol can effectively cleave the sulfonamide bond selectively, we herein report a dicyanoisophorone-based Red-emitting/NIR probe for thiophenol detection. This probe had some desirable properties such as rapid response, high selectivity and sensitivity, remarkable large Stokes shift (181 nm), Red-emitting/NIR fluorescence region and low LOD value (80 nM, according to 3σ/s). Moreover, this novel Red-emitting/NIR probe can potentially be applied to the detection of thiophenols in real water samples quantitatively and fluorescent imaging in living cells and zebrafishes.

A naphthalimide-indole fused chromophore-based fluorescent probe for instantaneous detection of thiophenol with a red emission and a large Stokes shift

This work presented a naphthalimide-indole fused chromophore-based fluorescent probe for the detection of thiophenol using 2,4-dinitrobenzene moiety as a sensing unit. This probe was able to work in aqueous media and instantaneously respond to thiophenol (within 5 min). In detecting thiophenol, this probe displayed a red emission (λmax = 590 nm), a 140 nm Stokes shift and a low detect limit (3.6 × 10−8 M). Furthermore, the potential ability for practical applications of this probe has been successfully demonstrated in monitoring thiophenol in living cells and in real water samples.

Reaction-based fluorescent probe for the selective and sensitive detection of thiophenols with a large Stokes shift and its application in water samples.

Although widely used in organic synthesis, pharmaceuticals and agrochemicals, thiophenol has brought about a series of ecological problems due to its high toxicity. Therefore, the development of efficient methods to discriminate thiophenols from aliphatic thiols is of great importance. In this work, a new reaction-based turn-on red fluorescence probe for the detection of thiophenols has been developed for the first time by employing dicyanomethylene-4H-pyran (DCM) as a fluorescence reporter and 2,4-dinitrobenzene-sulfonate (DNBS) as a recognition unit. The probe displayed a highly selective and sensitive (63 fold-fluorescence enhancement) response to thiophenols over aliphatic thiols. Additionally, the probe also exhibited a large Stokes shift (159 nm) and the detection limit reached as low as 8.3 nM. Moreover, this probe was also proved suitable for the quantification of thiophenol in real environmental water samples.

A red emitting fluorescent probe for instantaneous sensing of thiophenol in both aqueous medium and living cells with a large Stokes shift

A novel red emitting fluorescent probe for the instantaneous detection of thiophenol has been developed with a large Stokes shift. The successful application of this new probe for thiophenol detection in real water samples and living cells has been demonstrated.

A phthalimide-based fluorescent probe for thiophenol detection in water samples and living cells with a large Stokes shift

A phthalimide-based fluorescent probe for the detection of thiophenol was developed based on the combination of photo-induced electron transfer (PET) and excited-state intramolecular proton transfer (ESIPT) mechanisms. This probe displays high sensitivity and good selectivity toward thiophenol with a large Stokes shift (161 nm) and a low detection limit (3.5 nM, based on S/N=3). Furthermore, the applications of this probe for quantitative detection of thiophenol in real water samples and imaging intracellular thiophenol in living cells were successfully demonstrated.

Near-infrared fluorescent probe for detection of thiophenols in water samples and living cells.

The development of probes for rapid, selective, and sensitive detection of the highly toxic thiophenols is of great importance in both environmental and biological science. Despite the appealing advantages of near-infrared (NIR) fluorescent detection, no NIR fluorescent probes have been reported for thiophenols to date. Using the chemical properties of thiophenols that are able to cleave sulfonamide selectively and efficiently under mild conditions, we herein report a dicyanomethylene-benzopyran (DCMB)-based NIR fluorescent probe for thiophenols. This probe features remarkable large Stokes shift and shows a rapid, highly selective, and sensitive detection process for thiophenols with significant NIR fluorescent turn-on responses. The potential applications of this new NIR fluorescent probe were demonstrated by the quantitative detection of thiophenol in real water samples and by fluorescent imaging of thiophenol in living cells.