A near-infrared colorimetric fluorescent chemodosimeter for the detection of glutathione in living cells

Abstract

A novel near-infrared (NIR) and colorimetric fluorescent molecular probe based on a dicyanomethylene-4H-pyran chromophore for the selective detection of glutathione in living cells has been developed. The fluorescence OFF-ON switch is triggered by cleavage of the 2,4-dinitrobenzensulfonyl (DNBS) unit by the interaction with GSH.

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

“…The long wavelength (red to NIR region) molecular fluorescent probes are advantageous for in vivo bioimaging because of minimum photo-damage to biological samples, deep tissue penetration, and minimum interference from background auto-fluorescence by biomolecules in the living systems [22][23][24]. Generally, the fluorophore for detection of biological thiols is limited to coumarin [25], fluorescein [26], rhodamine [27] and cyanine [24,28], but others were reported less [29].…”

“…One of the most commonly used recognition methods in design of a chemodosimeter for biological thiols is the cleavage of sulfonic ester linker. Some electron-deficient sulfonic ester derivatives, such as 2,4-dinitrobenzenesulfonyl (DNBS) can act as fluorescence quencher and activator for nucleophilic reaction [22,23,34,48,57]. Rely on the electron density of these sulfonic ester derivatives, the sensitivity and selectivity of corresponding chemodosimeters can be adjusted quite easily.…”

“…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.…”

A near-infrared fluorescent probe for rapid detection of hydrogen peroxide in living cells

“…34 Compared with other NIR fluorophores like squaraine and cyanine, dicyanomethylene-4H-pyran (DCM) fluorophore is more photostable and is widely used in fluorescence imaging. [35][36][37][38][39][40] Our strategy for detection of H 2 O 2 bases on the introduction of styrene boronic acid moiety into benzopyran scaffold (Scheme 1). The near-infrared fluorescence OFF-ON switch is triggered by transformation of phenylboronic acid unit to phenol by the interaction with H 2 O 2 , which results in the formation of DPCOwithout the release of quinone methides.…”

A new ensemble approach based chemosensor for the reversible detection of bio-thiols and its application in live cell imaging

“…In the last two decades, enormous efforts have been devoted to the development of fluorescent chemosensors for the detection of thiols based on various chemical mechanisms, such as Michael addition [16][17][18], cyclization with aldehyde [19][20][21], disulfide bond cleavage reaction [22,23], binding with nanoparticles [24,25], cleavage of sulfonamide and sulfonate ester [26][27][28][29][30]. Recently, chemosensing ensemble-based displacement approach has been reported as one of new mechanisms for the thiols detection [31][32][33][34][35][36][37][38][39][40].…”