A reversible fluorescent probe for detecting hypochloric acid in living cells and animals: utilizing a novel strategy for effectively modulating the fluorescence of selenide and selenoxide

Abstract

Based on a novel strategy for modulating the fluorescence of selenide and selenoxide, we have designed and developed a reversible fluorescent probe for hypochloric acid. And the synthesis, characterization, fluorescence properties, as well as the biological applications in living cells and animals, have all been described. † Electronic supplementary information (ESI) available: Additional fluorescent confocal images, fluorescence spectra assays, TDDFT calculations, details of the synthesis, 1 H NMR, 13 C NMR, 77 Se NMR, MS spectra of compounds discussed in this communication. See

Development of a selenide-based fluorescent probe for imaging hypochlorous acid in lysosomes

“…1c, the fluorescence intensity decreased steadily upon the addition of GSH. This is in line with our former study that probes based on the redox states of selenide could be reduced after the reaction with ROS [36,37,42].…”

“…Fluorescent probes are powerful tools in cell biology and a variety of HOCl-sensitive probes have been developed for monitoring cellular HOCl under fluorescent microscopy [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37]. However, there are still opportunities to improve these probes in terms of selectivity, sensitivity, response speed and subcellular localization.…”

“…Besides the fluorophore, the structural key points of the probe are the selenide group and the (aminoethyl) morpholine moiety. Previous work has established that selenide could be selectively oxidized by HOCl [35][36][37], so we chose selenide as the fluorescent modulator. On the other hand, the morpholine moiety was expected to serve a function of leading this probe to lysosomes [38][39][40].…”

Fluorescent probes for hydrogen sulfide detection and bioimaging

“…Xian et al designed a series of turn-on probes (44,45) to detect H 2 S based on the dual nucleophilic property. 50,51 These fluorescent probes contained reactive disulfide groups.…”

Reversible Fluorescent Probes for Biological Redox States

“…5 [36] GSH 488/5144 -fold decrease HeLa -H 2 O 2 , a-lipoic acid and NEM Chalcogenoxides Cy-PSe [37] ONOO À 758/7752 3.3-fold increase RAW264.7 -SIN-1, GST,L PS, IFN-g,P MA, NOC-5 and TEMPO MPh-Se-BOD [38] -OCl 460/475-650 5f old increase RAW264.7 -PMA, Taurine, Xanth./Xanth. oxidase HCSe [39] -OCl 510/5261 38-fold increase RAW264.7 -NaOCl and GSH NI-Se [40] -OCl 420/5231 2-fold increase RAW264.7 -LPS, PMA and SHA Mice -LPS diMPhSe-BOD [41] HOBr 610/635, 700 230-fold increase RAW264.7 -H 2 O 2 ,EPO, KBr and H 2 S Bis(BODIPY)diselenide [42] O 2 C À 504/5143 0-fold increase MCF-7/ADRc ells -P MA 2Me TeR [43] -OCl (COH), (ONOO -PTZ [45] HOCl 450/605 % 7-fold increase Mice -NaOCl, H 2 Sand PABA FO-PSe [46] HOCl 415 (800) TP / 520 % 40-fold increase RAW264.7 -PMA, ABAH Zebrafish -Z ymosan and Mice abdomen Flavins CMFL-BODIPY [47] n.a.…”