Nile-Red-Based Fluorescence Probe for Selective Detection of Biothiols, Computational Study, and Application in Cell Imaging

Abstract

A new colorimetric and fluorescence probe NRSH based on Nile-red chromophore for the detection of biothiols has been developed, exhibiting high selectivity towards biothiols over other interfering species. NRSH shows a blue shift in absorption peak upon reacting with biothiols, from 587 nm to 567 nm, which induces an obvious color change from blue to pink and exhibits a 35-fold fluorescence enhancement at 645 nm in red emission range. NRSH displays rapid (<1 min) response for H2S, which is faster than other biothiols (>5 min). The detection limits of probe NRSH towards biothiols are very low (22.05 nM for H2S, 34.04 nM for Cys, 107.28 nM for GSH and 113.65 nM for Hcy). Furthermore, NRSH is low cytotoxic and can be successfully applied as a bioimaging tool for real-time monitoring biothiols in HeLa cells. In addition, fluorescence mechanism of probe NRSH is further understood by theoretical calculations.

Synthesis of a Novel Electrochemical Probe for the Sensitive and Selective Detection of Biothiols and Its Clinical Applications

“…DNBS moiety is well-known as a specific recognition moiety for the selective determination of biothiols. − The novelty of this work is the designing of a simple and selective “signal on” type electrochemical probe for biothiols detection dependent on the attachment of DNBS group to a highly electroactive compound called p -aminophenol. As mentioned above selecting p -aminophenol for the synthesis of arenesulfonamide protecting group increases the probe selectivity toward biothiols by improving the probe’s resistance toward other nucleophiles such as oxygen and nitrogen nucleophiles.…”

Design and Development of a New Type of Hybrid PLGA/Lipid Nanoparticle as an Ursolic Acid Delivery System against Pancreatic Ductal Adenocarcinoma Cells

“…The next step was to evaluate the cellular uptake of the nanoparticles. For this purpose, we labeled nanoparticles with Nile Red, which is commonly used for bioimaging studies [ 46 ]. Confocal microscopy observation was performed using fluorescence signals from two fluorophores: one from cell nuclei stained with DAPI and the second from Nile Red encapsulated in nanoparticles, with the addition of transmitted light.…”

Enlightening the Path to Protein Engineering: Chemoselective Turn-On Probes for High-Throughput Screening of Enzymatic Activity

“…Upon reaction with thiolates, the benzenesulfonamide or benzenesulfonate bond is cleaved, SO 2 is released, and fluorescence is restored (Figure ). − In 2005, Maeda et al . developed the DNBS-based probe BESThio 222 , which showed a high increase in fluorescence within minutes upon reaction with thiols under mild aqueous conditions (pH 7.4, 37 °C).…”