A mitochondria targetable near-infrared fluorescence probe for glutathione visual biological detection

Abstract

A mitochondria targetable fluorescence probe with 730 nm emission was developed for GSH detection. The probe successfully imaged GSH in HeLa cells and C. elegans, and was applied in rat brain slices imaging.

Multiple fluorescence and hydrogen peroxide-responsive properties of novel triphenylamine–benzothiazole derivatives

“…Generally, screening time-dependant uorescence behavior is required in real-time detection of substances. 38,39 To explore the H 2 O 2 response of BZT-TPA-BO, we monitored the timeresponsive change of uorescence intensity at 575 nm. As indicated in Fig.…”

A water-soluble fluorescent probe for monitoring mitochondrial GSH fluctuations during oxidative stress

“…According to the published literature, the possible reaction mechanism between MITO-PQDNs and GSH was presented in Scheme 1. 20,22,[37][38][39] The strong electron-absorbing DNs group signicantly quenched the uorescence of MITO-PQDNs. However, the strongly nucleophilic GSH could undergo a nucleophilic aromatic substitution reaction (SNAr) with MITO-PQDNs leading to the cleavage of the sulfonate esters, thus releasing the uorophore MITO-PQ.…”

“…21 The 2,4-dinitrophenylsulfonyl (DNs) group with strong electronabsorbing ability could signicantly quench the uorescence of the uorophore MITO-PQ and react with the sulydryl group of GSH, so the DNs group was selected as the recognition moiety for MITO-PQDNs. 20,22 Furthermore, the pyridine salt moiety with a positive charge could bind tightly to the inner mitochondrial membrane with a negative potential of −180 mV, which allowed the probe MITO-PQDNs to be selectively enriched in mitochondria. [23][24][25][26][27][28] However, most of the available pyridinium probes had small Stokes shis, resulting in strong self-absorption which would be detrimental to uorescence imaging applications.…”

“… 19 In 2022, Zhou et al designed a near-infrared (NIR) fluorescent probe JGP based on the intramolecular charge transfer (ICT) mechanism to monitor mitochondrial GSH. 20 The probe JGP was composed of a cyanine fluorophore, an indole ammonium cation targeting group and a 2,4-dinitrobenzenesulfonyl recognition site, and triumphantly achieved the bioimaging of GSH in Caenorhabditis elegans and rat brain slices. However, these fluorescent probes, which possessed poor water-solubility, could usually only detect analytes in solutions containing organic cosolvents.…”