A simple hypochlorous acid signaling probe based on resorufin carbonodithioate and its biological application

Abstract

A novel HOCl signaling probe based on the oxidative hydrolysis of resorufin carbonodithioate to generate resorufin dye was investigated and applied to cell imaging.

Highly sensitive and rapid detection of hypochlorous acid in aqueous media and its bioimaging in live cells and zebrafish using an ESIPT-driven mycophenolic acid-based fluorescent probe

“…While thiol-based probes have demonstrated their ability to detect Hg 2+ , 45,46 their sensitivity to interference from Hg 2+ has not been a major concern in most biological applications due to the typically low concentrations of these metal ions. 47,48 We additionally confirmed that the Myco-OCl probe interacts with the thiophilic metal ion Hg 2+ displaying a low fluorescence signal (Fig. 1).…”

Fluorescent Probes for HOCl Detection in Living Cells

“…Thus, among the trends in the development and application of small-molecule probes for detecting HOCl, one can note the frequent use of DAMN as a target for HOCl in sensors, for example, in CSN [63], RO610 [78], compound (VIII) [90], and HQMN [91]. A new branch was the use of probes based on phenoxazine (CB [70], RT-1 [73], BR-O [74], BR-1 [75], BC-2, and BC-3 [77]), as well as a hybrid fluorophore rhodol (RO610 [78], HKOCl-4, and its derivatives [79]). Of interest is the strategy of simultaneous registration of several types of oxidants, implemented, for example, in the work of Zhang et al [67] using the FHZ probe as an example.…”

“…(d) For kinetic studies of HOCl formation (reaction time <1 min), all probes other than BCO and BETC (reaction time not determined) [62], FN-1 and FN-2 [69], RT-1 [73], BR-O [74], BR-1 [75], Dcp-EPtz [88], EtS-DMAB [92], NSSN [93].…”

“…In 2019, Choi and coauthors presented the RT-1 turn-on probe based on a carbonodithioate derivative of resorufin (Fig. 9) [73]. Hydrolysis of the car-bonodithioate fragment under the action of HOCl leads to the release of fluorescent resorufin (λ ex = 550 nm; λ em = 587 nm).…”

“…The disadvantages of the probe include a drop in the fluorescence intensity of resorufin in the presence of bromide and iodide ions, as well as a strong dependence of the ratio of the fluorescence intensity of resorufin to the fluorescence intensity of RT-1 on the pH value of the medium (optimum at pH 8). RT-1 was used to visualize exogenous HOCl in RAW264.7 and HeLa cell lines [73].…”