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

Abstract

The ability to estimate and quantify biothiols in biological fluids is very significant for attaining a detailed understanding of biothiols-related pathological diseases. Most of the developed methods for biothiols detection are not suitable for this purpose owing to their low sensitivity, poor selectivity, and long experimental procedures. In this study, a novel and simple structure electrochemical probe has been synthesized for the first time for the selective determination of biothiols. The developed probe is based on using 2,4-dinitrobenzenesulfonyl moiety (DNBS) as a selective recognition moiety for biothiols. The electrochemical probe was successfully fabricated through a facile one-step reaction between 2,4-dinitrobenzenesulfonyl chloride (DNBS-Cl) and p-aminophenol. The successful synthesis of the probe was confirmed by using different characterization techniques such as an NMR spectroscopy, Fourier-transform infrared (FT-IR) spectroscopy, and mass spectrometry. Biothiols can selectively cleave the DNBS moiety through an aromatic nucleophilic substitution (ANS) reaction within 10 min to release p-aminophenol, which is a highly electrochemical active molecule that can be selectively detected easily by cyclic voltammetry at low potential. The probe has been employed for the quantification of cysteine, glutathione, and homocysteine with a LOD of 1.50, 3.48, and 4.67 μM, respectively. Excellent recoveries have been achieved in the range of 95.44–98.71% for the determination of the total biothiols in the human plasma sample.

Electrochemiluminescence from Single Molecule to Imaging

“…Rational design of the reaction system and optimization of reaction efficiency empowers single-molecule ECL microscopy with a higher spatiotemporal resolution, and also improves the signal-to-noise ratio of single-molecule detection. The discovery, design, and synthesis of new ECL probes are consistent with this goal. − To expand the available choice of ECL luminophores, Guo et al reported several new ruthenium­(II) and iridium­(III) complexes for synthesis, photophysics, electrochemistry, and ECL phenomenon, some of which were eventually adopted as signal probe molecules for multiplexed immunoassays (Figure B). The ECL behavior of a single luminophore and the mixture of several luminophores, including light intensity, spectrum, , and image measurement, was studied in various modes, and the potential-color resolved ECL signal capable of recognizing multiple antigens or nuclei acids could be a unique dimension of ECL microscopy utilizing the chemical interactions.…”

Simple and Cost-Effective Quantum Dot Chemodosimeter for Visual Detection of Biothiols in Human Blood Serum

“…8 Selective detection and quantification of these biologically important analytes are major difficult tasks due to their structural similarity, incorporating both carboxylic and amino functionalities. Various approaches for qualitative as well as quantitative analysis of these bioanalytes have been developed, mainly based on electroanalytical techniques, 9,10 high-performance liquid chromatography (HPLC), 11,12 capillary electrophoresis separation, immunoassays based on derivatization with fluorescent/phosphorescent reagents, spectrophotometric methods, etc. 13,14 Unfortunately, all of these methods require either expensive reagents or equipment or skilled manpower to ensure reproducibility.…”

“…Selective detection and quantification of these biologically important analytes are major difficult tasks due to their structural similarity, incorporating both carboxylic and amino functionalities. Various approaches for qualitative as well as quantitative analysis of these bioanalytes have been developed, mainly based on electroanalytical techniques, , high-performance liquid chromatography (HPLC), , capillary electrophoresis separation, immunoassays based on derivatization with fluorescent/phosphorescent reagents, spectrophotometric methods, etc. , Unfortunately, all of these methods require either expensive reagents or equipment or skilled manpower to ensure reproducibility. In this context, much attention is being paid to the development of simple and cheap fluorescent probes, without compromising selectivity and sensitivity. − Nanoparticles have been proven to be an efficient substitute for organic fluorophores, particularly for developing emission “turn on/off” sensors. − Among various nanoparticles, quantum dots (QDs) are of particular interest in developing novel biosensors owing to their unique properties such as broad absorption band, emission in the visible region, photostability, etc. − Moreover, the potential of QDs to transfer electrons or holes to biologically important molecules, interacting covalently or noncovalently with their surface, can be used to tune the QD emission intensity and thus generate charge transfer-based emission “on/off” signaling. − …”

Review on Carbon Dot-Based Fluorescent Detection of Biothiols

“…To detect and quantify the biothiols, numerous tactics have been proposed, including colorimetric assay, electrochemical methods, fluorescent imaging, surface enhanced Raman spectroscopy, etc. [ 29 , 30 , 31 , 32 ]. Among them, fluorescent imaging is rather impressive in terms of the real-time monitoring of biothiols in living tissues or cells [ 33 , 34 ].…”