A colorimetric and fluorometric BODIPY probe for rapid, selective detection of H2S and its application in live cell imaging

Abstract

A BODIPY-azide based colorimetric and fluorescence turn-ON probe for rapid, selective and sensitive detection of H2S is reported. The probe displayed a fast response time (10 min in HEPES and 30 s in serum albumin), 28-fold fluorescence enhancement and low detection limit up to 259 nM. The application of the probe to the estimation of H2S in live cells was demonstrated.

“On demand” redox buffering by H2S contributes to antibiotic resistance revealed by a bacteria-specific H2S donor

“…A H 2 S-sensitive dye BODIPY-azide 4a was employed to detect H 2 S. BODIPY-azide is known to be reduced by H 2 S to produce a fluorescent amine 4b . 14 Compounds 1a–1g were independently exposed to NTR and all compounds were found to generate H 2 S under these conditions ( Fig. 2a ).…”

Chemical probes for molecular imaging and detection of hydrogen sulfide and reactive sulfur species in biological systems

“…Reporters for H 2 S based on coumarin ( 8-9 ), 70,71,72 2-(2-aminophenyl)benzothiazole ( 10 ), 73 7-nitrobenz-2-oxa-1,3-diazole ( 11 ), 74 dicyanomethylenedihydrofuran ( 12 ), 75 resorufamine ( 13 ), 76 BODIPY ( 14 ), 77 phenanthroimidazole ( 15 ), 78 and the 1,8-naphthalimide scaffold ( 16 ) 79 have been described, including a lysosomally-targeted derivative ( 17 ). 80 The Pluth laboratory has also developed the first chemiluminescent H 2 S probe 18 based on an azido derivative of luminol, which can be used to detect enzymatically-produced H 2 S in vitro .…”

BODIPY‐Based Fluorescent Probes for Biothiols

“…The azide moiety, as a representative recognition group of H 2 S, was attached to a wide array of amine‐containing fluorophores to regulate the optical signals as demonstrated in the pioneering works from both the Chang group and the Wang group, through the chemoselective reduction of azides to amines by H 2 S. Talukdar and co‐workers directly linked an azide moiety onto the 3‐position of the BODIPY core to develop probe 1 (Figure ) with 28‐fold fluorescence turn‐on in HEPES buffer (10 m m , pH 7.4) and displayed green fluorescence in HeLa cells upon treatment with Na 2 S . The weak fluorescence of probe 1 was believed to be induced by photoinduced electron transfer (PET), which takes place from the electron‐rich α‐nitrogen of the azido group to the electron‐poor BODIPY core.…”