An NBD‐Based Mitochondrial Targeting Ratiometric Fluorescent Probe for Hydrogen Sulfide Detection

Abstract

Hydrogen sulfide (H2S) is an important endogenous gaseous signaling molecule with multiple biological functions. In this study, an NBD‐based ratiometric fluorescent probe (MR‐1) was successfully designed and synthesized for selectively detection H2S. The probe exhibits high selectivity and fast emission intensity ratio changes in response to H2S in solution. The modification of triphenylphosphine in the probe enables it to be used for the imaging mitochondrial H2S in living HeLa cells.

Characterization of Dialkyldithiophosphates as Slow Hydrogen Sulfide Releasing Chemicals and Their Effect on the Growth of Maize

“…There are numerous methods to monitor the release of H 2 S, such as the use of gas chromatography, HPLC, H 2 S electrodes, and fluorescent probes and the formation of tin sulfide. − Recent work has focused on the development of probes that strongly fluoresce after reacting with H 2 S and that can work in cellular environments. We chose to investigate the hydrolysis of dibutyldithiophosphate by 31 P NMR spectroscopy and by use of a H 2 S electrode.…”

Small‐Molecule Quenchers for Förster Resonance Energy Transfer: Structure, Mechanism, and Applications

“…AlexaFluor 488 (72 000; 516)/fluorescein Detect bromo-benzophenanthridinone 968 on glutaminase C (GAC) [74] /liposome [77 Detect cathepsins L, K or S, [62] caspase-3, [63] MMP-2, [65] cysteine cathepsin (CTS), [69] cathepsin S, [70] intracellular hypoxia [79] /fusion proteins [68] /pH [71] /β-Lactamase (BlaC) [73] /Glucose [82] Quantify the degradation of antibodies [91] /detect thrombin, [92] miRNA, [93] β-lactamase, [96] caspase-3 [99] /enzyme [94] /metalloprotease ADAMTS13 [95] /2-deoxyglucose (2-DG) [97] Monitor the activity of acid sphingomyelinase (ASM) [100] /ASM activity, [101] detect H 2 S [103][104][105][106][107] / influenza virus-mediated membrane fusion [109] /Phospholipase A2 (PLA2) [116] /sense the polymer conformational changes [119] DYQ Monitor the translocation of the deacetylated tRNA [125] /investigate the binding sites' changes of the N-and C-terminus of initiation factor 3 (IF3) on small ribosomal subunit (30S) platform [126] /label mRNA [127] /tRNA [128] ATTO 575Q 582 Detect retroviruses Human T-cell leukemia virus type 1 (HTLV-1) and HIV-1 simultaneously [133] /monitor minimal residual disease (MRD) [134] /rapid detection of SARS-CoV-2 [135] BMN-Q590 CBG-488/thio-BODIPY/FAM Manipulate protein functions in living cells [68] /detect GSH…”

“…[102] A FRET-based ratiometric fluorogenic probe was used to detect mitochondrial H 2 S by conjugating the probe with mitochondrial targeting group triphenylphosphine (TPP) (Figure 9c). [103] Upon addition of H 2 S, the new absorption peak at 530 nm emerged due to the formation of the NBD-SH bond and the emission band of coumarin at 415 nm appeared (Φ, 0.0501). NBD has also been used to pair with coumarin, [104] rhodamine, [105] ANN, [106] acetoxymethyl ester (AM), and BODIPY [107] for the detection of H 2 S in vitro and in vivo.…”

“…A recent study showed that the serum H 2 S levels in COVID‐19 patients are significantly higher than that of uninfected ones [102] . A FRET‐based ratiometric fluorogenic probe was used to detect mitochondrial H 2 S by conjugating the probe with mitochondrial targeting group triphenylphosphine (TPP) (Figure 9c) [103] . Upon addition of H 2 S, the new absorption peak at 530 nm emerged due to the formation of the NBD‐SH bond and the emission band of coumarin at 415 nm appeared ( Φ , 0.0501).…”

A fast-responsive fluorescent probe based on a styrylcoumarin dye for visualizing hydrogen sulfide in living MCF-7 cells and zebrafish

“…This is associated with many illnesses, such as diabetes, mental decline, cardiovascular diseases, and cancer. [10][11][12][13] Therefore, the accurate measurement of H 2 S in organisms and the environment is of great signicance for in-depth studies on the pathogenesis of related diseases.…”