Diketopyrrolopyrrole-based ratiometric fluorescent probe for the sensitive and selective detection of cysteine over homocysteine and glutathione in living cells

Abstract

A new fluorescent probe (DPP-AC) based on diketopyrrolopyrrole with an acrylate group was designed and synthesized for the sensitive and selective detection of biological thiols.

Galactose functionalized diketopyrrolopyrrole as NIR fluorescent probes for lectin detection and HepG2 cell targeting based on aggregation-induced emission mechanism

“…Diketopyrrolopyrrole (DPP) and their derivatives have attracted considerable research interests over the last few decades due to their relatively simple synthesis, intense color and excellent photo-stability. Currently, DPPs have been extensively applied in construction of materials for twophoton absorption [23,24], fluorescent probes [25][26][27] and imaging [28,29]. DPP derivatives functionalized with electron donor groups usually exhibit red to near-infrared (NIR) emission and large Stokes shifts that are advantageous in biological applications [30][31][32][33].…”

Electrochemical Molecular Switch for the Selective Profiling of Cysteine in Live Cells and Whole Blood and for the Quantification of Aminoacylase-1

“…These results indicated that, in contrast to Cys, these other biothiols could not effectively participate in the intramolecular cyclization and hence not initiate the subsequent disassembly of the probe to release AF under ambient test conditions. The results were consistent with earlier findings of acrylate-based fluorescent indicators showing selective detection of Cys over other biothiols. ,, …”

“…The common amino acids and biothiols do not make any significant alteration in the response current of Cys; these analytical results were in agreement with the Cys-selective fluorescent indicators. 27,28 Thus, the results showed the designed probe to have excellent selectivity for Cys over other biothiols and over large amounts of other potentially interfering species. Further, the interaction of the probe with active sulfur species such as NaHS, Na 2 S, Na 2 S 2 O 3 , and polysulfides (S 2 2− , S 3 2− , and S 4 2− ) were analyzed in the presence and absence of Cys.…”

“…The results were consistent with earlier findings of acrylate-based fluorescent indicators showing selective detection of Cys over other biothiols. 20,27,28 Despite the advantages of electrochemical instrumentation over fluorescence instruments, electrochemical approaches have scarcely been reported for the selective detection of Cys in the presence of Hcy. Discriminating the voltammetric signals of Cys and Hcy is a challenging task using traditional electrochemical methods, as these molecules are structurally similar and differ by only a single methylene group.…”

“…The enhanced selectivity results from the Michael addition of Cys-sulfur to acrylate with a subsequent intramolecular cyclization of Cys-amine to generate electrochemical signal over conventional thiolinduced electrochemical signal. 20,27,28 The unique discrimination of Cys over Hcy by FCPA can be accounted for by the kinetically restricted intramolecular cyclization of the Hcy− acrylate adduct to yield the eight membered cyclic product. Indeed, the thiol addition of Hcy with acrylate requires an almost equal time to the completion on matching with the overall reaction time between Cys with acrylate esters.…”