Hypochlorous Acid Turn-on Fluorescent Probe Based on Oxidation of Diphenyl Selenide

Abstract

A BODIPY-based fluorescent probe, HCSe, has been successfully developed for the rapid detection of hypochlorous acid based on the specific HOCl-promoted oxidation of diphenyl selenide in response to the amount of HOCl. Confocal fluorescence microscopy imaging using RAW264.7 cells showed that the new probe HCSe could be used as an effective fluorescent probe for detecting HOCl in living cells.

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.…”

“…[38] An umber of additional probes have been developed based on this strategy.H CSe contains aB ODIPY scaffold linked to ad iphenyl selenide,a nd undergoes reversible oxidation with OCl À to the green fluorescent HCSeO,b ut no information on the selectivity for reducing agents is available. [39] NI-Se contains a1,8-naphthalimide fluorophore, and is sensitive to the OCl À /H 2 Sr edox couple. [40] This probe operates by the twisted intramolecular charge-transfer (TICT) mechanism, in which the selenoxide formed upon oxidation restricts the internal rotation of the molecule,t hus leading to enhanced fluorescence emission.…”

Using photochemistry to understand and control the production of reactive oxygen species in biological environments

“…[51] In the last years, organoselenium chemistry was also exploited in the design of new PeT probes for the detection of HOCl. [52,53] The interesting aspect of these probes is that the selenoxide fluorescent "on" state can be recycled to the selenide "off" state by reduction with either glutathione or H 2 S. [52,53] PeT probes for sensing the highly reactive  OH radical were obtained by covalently joining the nitroxide TEMPO receptor to a BODIPY reporter (TEMPO-BDP, Fig. 5b).…”

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

“…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].…”