A Naphthalimide-Based Glyoxal Hydrazone for Selective Fluorescence Turn-On Sensing of Cys and Hcy

Abstract

A fluorescent turn-on probe for Cys/Hcy based on inhibiting the C═N isomerization quenching process by an intramolecular hydrogen bond was reported. The probe exhibited higher selectivity toward Cys/Hcy over other amino acids as well as thiol-containing compounds.

A New Turn on Fluorescent Probe for Selective Detection of Cysteine/Homocysteine

“…In combination with the previous conclusions by other groups [17], a possible mechanism was proposed as shown in Scheme 2. The spectroscopic responses of 1 toward Cys/ Hcy could be ascribed to the cyclization reaction of aldehyde group in 1 with Cys/Hcy.…”

“…The cyclization reaction of aldehyde group in probe 1 with Cys/Hcy would result in the formation of thiazolidines/ thiazinanes. The five-membered cyclic intramolecular hydrogen bond [17] between thiazolidine/thiazinane NH and the imine N atom in 1-Cys/1-Hcy would prevent the C=N bond isomerization-induced quenching, thereby causing a fluorescence enhancement of the system. The data of ESI mass spectrum provided evidence of the cyclization of Cys with probe 1 in CH 3 Figure S3 in Supplementary information).…”

“…Significant efforts have been devoted to construction of fluorescent probes for biothiols [7]. Many fluorescent probes involved in different detecting mechanisms have been developed for thiols detecting, such as Michael addition reaction [8][9][10][11][12][13][14][15][16], cyclization reaction based on aminothiols and aldehyde [17][18][19][20][21], cleavage reaction induced by thiols [22][23][24][25][26][27][28][29][30], and ligand displacement of metal complexes by thiols [31][32][33].…”

A multi-emissive fluorescent probe for the discrimination of glutathione and cysteine

“…For instance, the selective detections of Cys/Hcy were usually performed based on the strategy of cyclization with aldehydes (Rusin et al, 2004;Wang et al, 2012;Barve et al, 2014) and conjugate addition-cyclization with acrylates (Yang et al, 2011;Niu et al, 2016;Han et al, 2015;Guo et al, 2012). On the other hand, the discriminations of GSH from Cys were achieved using aromatic substitution-rearrangement reactions, etc (Niu et al, 2012;Wang et al, 2014c;Lim, 2014;Niu et al, 2015c;Işık et al, 2014).…”

Photostable red turn-on fluorescent diketopyrrolopyrrole chemodosimeters for the detection of cysteine in living cells

“…These processes of detecting thiols involve a specific reaction such as cleavage reaction by thiol [9,22,33,34,[47][48][49], cyclization with aldehyde [27,[50][51][52][53], metal complex-displacement coordination [54], and others [23,55,30,56]. One of the most commonly used recognition methods in design of a chemodosimeter for biological thiols is the cleavage of sulfonic ester linker.…”