BODIPY‐based Fluorescent Probe for Fast Detection of Hydrogen Sulfide and Lysosome‐targeting Applications in Living Cells

Abstract

Hydrogen sulfide (H 2 S) is recognized as an endogenous gaseous signaling agent in many biological activities. Lysosomes are the main metabolic site and play a pivotal role in cells. Herein, we designed and synthesized two new fluorescent probes BDP-DNBS and BDP-DNP with a BODIPY core to distinguish H 2 S. The sensing mechanism is based on the inhibition-recovery of the photo-induced electron transfer (PET) process. Through comparing the responsive behaviors of the two probes toward H 2 S, BDP-DNBS showed a fast response time (60 s), low limit of detection (LOD, 51 nM), high sensitivity and selectivity. Moreover, the reaction mechanism was demonstrated by mass spectrometry and fluorescence off-on mechanism was proved by density functional theory (DFT). Significantly, confocal fluorescence imaging indicated that BDP-DNBS was successfully used to visualize H 2 S in lysosomes in living HeLa cells.

Photoinduced electron transfer (PeT) based fluorescent probes for cellular imaging and disease therapy

“…10A) to detect H 2 S in lysosomes. 75 BODIPY was used as the core fluorophore, and a dinitrophenoxy-moiety (DNP) or dinitrobenzenesulfonyl-moiety (DNBS) were incorporated into probe 11 and probe 12 , respectively. In particular, DNBS was selected because reaction with H 2 S could result in the cleavage of the group, exposing an electron rich phenol which in biological media becomes a phenolate group.…”

Novel fluorescent probe based on dicoumarin for detection of hydrogen sulfide in real samples

“…[33] In addition, due to its extremely fast and highly specific nucleophilic substitution between H 2 S and the active sensing moiety, H 2 S detection is independent of other gases and active molecules and is therefore susceptible to biological thiols decomposition, which opens the probe's luminescence switch. [34][35][36][37][38][39][40] Herein, we developed a novel fluorescent probe coumarin fused heterocycle (DC-HS) by fusing the fluorophore dicoumarin with the DNBS group (Scheme 1). Because 2,4-dinitrobenzylsulfonyl may stop ICT, the probe is nonfluorescent.…”

“…[ 33 ] In addition, due to its extremely fast and highly specific nucleophilic substitution between H 2 S and the active sensing moiety, H 2 S detection is independent of other gases and active molecules and is therefore susceptible to biological thiols decomposition, which opens the probe's luminescence switch. [ 34–40 ]…”

A New Ratiometric Fluorescent Probe Based on BODIPY for Highly Selective Detection of Hydrogen Sulfide

“…Among numerous fluorophores, Boron dipyrromethenes (BODIPY) dyes have been widely applied in fluorescence sensing and imaging because of their high absorption coefficient, excellent fluorescent quantum yield and high photo-stability [ 15 , 16 ]. So far, tremendous efforts have been devoted to the exploitation of BODIPY-based fluorescent probes for monitoring and imaging of endogenous hydrogen sulfide in living cells with high sensitivity and low detection limits [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 ]. However, most of the reported H 2 S fluorescent probes based on BODIPY are focused on the “turn-on” or “turn-off” detection model in which the fluorescence intensity of probes increases with the concentration of hydrogen sulfide.…”

“…The following supporting information can be downloaded at: , Table S1: The BODIPY-based fluorescent probes for detection of H 2 S; Figure S1: The absorption ratio at 568 nm and 516 nm of probe BH (5 μM) toward different concentration of H 2 S in aqueous solution of DMSO/PBS ( v / v 1/1, pH 7.4); Figure S2: The fluorescence intensity at 568 nm and 516 nm of probe BH (5 µM) toward increasing H 2 S concentration (0−500 μM) in aqueous solution of DMSO/PBS ( v / v 1/1, pH 7.4); Figure S3: Linear relationship of the fluorescence intensity ratio (I 594nm /I 542nm ) of probe BH toward H 2 S concentration (0−75 μM); Figure S4: ESI-MS spectrum of reaction product of probe BH with H 2 S; Figure S5: The fluorescence intensity ratios (I 594nm /I 542nm ) of probe BH (5 μM) in the absence (●) or presence ( ■ ) of H 2 S (500 μM) at various pH values [ 18 , 19 , 20 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 37 , 38 , 39 , 40 ].…”