A selective fluorescent probe for thiols based on α,β-unsaturated acyl sulfonamide

Abstract

We report herein a novel fluorescent probe based on α,β-unsaturated acyl sulfonamide to detect thiols. The probe has good water solubility and reacts with thiols under aqueous conditions. It reacts selectively with cysteine but not with the other natural amino acids. The probe was subsequently applied to detect intracellular thiols.

An ‘OFF–ON’ fluorescent probe for specially recognize on Cys and its application in bioimaging

“…Their abnormal levels are linked to a number of diseases. The deficiency of Cys is involved in many human diseases, such as delayed growth, lethargy, hair depigmentation, skin lesions, liver damage, muscle and fat loss, and so on [4][5][6][7][8][9][10]. As determined by elevated plasma levels, Hcy is a risk factor for Alzheimer's disease [11,12].…”

A minimalist fluorescent probe for differentiating Cys, Hcy and GSH in live cells

“…5 Over the last decade, a large number of fluorescent probes have been developed for detecting thiols. 6 Most of these probes are based on thiol-selective chemical reactions, including Michael addition reactions, 7 nucleophilic substitution, 8 cyclization reactions between aldehyde and aminothiols, 9 cleavage reactions of 2,4-dinitrobenzenesulfonyl (DNBS) with thiols, 10 disulfide exchange reaction, 11 and others. 12 …”

A Vinyl Sulfone‐Based Fluorogenic Probe Capable of Selective Labeling of PHGDH in Live Mammalian Cells

“…By replacing sulfonamide in these fluorophores with vinyl sulfone (giving DNS‐pE, DNS‐E, and SBD‐E, respectively; Figure B), our newly designed probes might provide a unique starting point to develop novel fluorogenic PHGDH probes. We further noted that our probes are also structural analogues of two well‐known thiol‐reactive fluorogenic small molecules, that is, acrylodan and DNS‐D (Supporting Information, Figure S1) . As controls, probes containing a sulfonyl fluoride (SF) were also examined (PSF in Figure A, DNS‐pF/DNS‐F/SBD‐F in Figure B); with numerous reports on biocompatible SF‐based compounds as emerging electrophilic probes capable of modifying different nucleophilic residues in proteins, these probes may help to expand the potential ligandable region around the PHGDH active site.…”

“…Several cysteine‐reactive, electrophilic α,β‐unsaturated moieties, including ketones, amides, and vinyl sulfonamides, are known fluorescence quenchers in suitably designed small molecule fluorophores . We took note of the structural and electronic similarities between vinyl sulfone and sulfonamide, an acceptor moiety commonly used in push‐pull fluorophores, including 2,6‐dansyl amide, dansyl amide, and 4‐sulfamoyl‐7‐aminobenzoxadiazole (Supporting Information, Figure S1) . By replacing sulfonamide in these fluorophores with vinyl sulfone (giving DNS‐pE, DNS‐E, and SBD‐E, respectively; Figure B), our newly designed probes might provide a unique starting point to develop novel fluorogenic PHGDH probes.…”