Browse
Submit Data
Databases
API
Help

Dataset Information

33 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Sensitivity and Selectivity Analysis of Fluorescent Probes for Hydrogen Sulfide Detection.

ABSTRACT: Hydrogen sulfide (H₂ S) is a gasotransmitter known to regulate physiological and pathological processes. Abnormal H₂ S levels have been associated with a range of conditions, including Parkinson's and Alzheimer's diseases, cardiovascular and renal diseases, bacterial and viral infections, as well as cancer. Therefore, fast and sensitive H₂ S detection is of significant clinical importance. Fluorescent H₂ S probes hold great potential among the currently developed detection methods because of their high sensitivity, selectivity, and biocompatibility. However, many proposed probes do not provide a gold standard for proper use and selection. Consequently, issues arise when applying the probes in different conditions. Therefore, we systematically evaluated four commercially available probes (WSP-1, WSP-5, CAY, and P3), considering their detection range, sensitivity, selectivity, and performance in different environments. Furthermore, their capacity for endogenous H₂ S imaging in live cells was demonstrated.

SUBMITTER: Zhou Y

PROVIDER: S-EPMC9306468 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Reaction based fluorescent probes for hydrogen sulfide.

Project description:A reaction based fluorescence turn-on strategy for hydrogen sulfide (H(2)S) was developed. This strategy was based on a H(2)S-specific Michael addition-cyclization sequence. Other biological thiols such as cysteine and glutathione did not pursue the reaction and therefore did not turn on the fluorescence/consume the substrates. The probes showed good selectivity and sensitivity for hydrogen sulfide.

| S-EPMC3336739 | biostudies-literature

Low-Cytotoxicity Fluorescent Probes Based on Anthracene Derivatives for Hydrogen Sulfide Detection.

Project description:Owing to the role of H2S in various biochemical processes and diseases, its accurate detection is a major research goal. Three artificial fluorescent probes based on 9-anthracenecarboxaldehyde derivatives were designed and synthesized. Their anion binding capacity was assessed by UV-Vis titration, fluorescence spectroscopy, HRMS, 1HNMR titration, and theoretical investigations. Although the anion-binding ability of compound 1 was insignificant, two compounds 2 and 3, containing benzene rings, were highly sensitive fluorescent probes for HS- among the various anions studied (HS-, F-, Cl-, Br-, I-, AcO-, H2PO4- , SO32- , Cys, GSH, and Hcy). This may be explained by the nucleophilic reaction between HS- and the electron-poor C=C double bond. Due to the presence of a nitro group, compound 3, with a nitrobenzene ring, showed stronger anion binding ability than that of compound 2. In addition, compound 1 had a proliferative effect on cells, and compounds 2 and 3 showed low cytotoxicity against MCF-7 cells in the concentration range of 0-150 μg·mL-1. Thus, compounds 2 and 3 can be used as biosensors for the detection of H2S in vivo and may be valuable for future applications.

| S-EPMC6024568 | biostudies-literature

Fluorescent probes based on nucleophilic substitution-cyclization for hydrogen sulfide detection and bioimaging.

Project description:The design, synthesis, properties, and cell imaging applications of a series of 2-pyridyl disulfide based fluorescent probes (WSP1, WSP2, WSP3, WSP4 and WSP5) for hydrogen sulfide detection are reported. The strategy is based on the dual-nucleophilicity of hydrogen sulfide. A hydrogen sulfide mediated tandem nucleophilic substitution-cyclization reaction is used to release the fluorophores and turn on the fluorescence. The probes showed high sensitivity and selectivity for hydrogen sulfide over other reactive sulfur species, including cysteine and glutathione.

| S-EPMC4049170 | biostudies-literature

Genetically anchored fluorescent probes for subcellular specific imaging of hydrogen sulfide.

Project description:Imaging hydrogen sulfide (H2S) at the subcellular resolution will greatly improve the understanding of functions of this signaling molecule. Taking advantage of the protein labeling technologies, we report a general strategy for the development of organelle specific H2S probes, which enables sub-cellular H2S imaging essentially in any organelles of interest.

| S-EPMC4747831 | biostudies-literature

Selective turn-on fluorescent probes for imaging hydrogen sulfide in living cells.

Project description:Hydrogen sulfide (H(2)S) is an important biological messenger but few biologically-compatible methods are available for its detection. Here we report two bright fluorescent probes that are selective for H(2)S over cysteine, glutathione and other reactive sulfur, nitrogen, and oxygen species. Both probes are demonstrated to detect H(2)S in live cells.

| S-EPMC3340910 | biostudies-literature

A Visible Colorimetric Fluorescent Probe for Hydrogen Sulfide Detection in Wine.

Project description:A new efficient and practical fluorescent probe 6-(benzo[d]thiazol-2-yl)naphthalen-2-yl-thiophene-2-carboxylate (probe 1) was synthesized to detect hydrogen sulfide (H2S). The addition of H2S caused the solution of probe 1 to change from colorless to yellow, and the solution of probe 1 changes to different colors with respect to different concentrations of H2S. Importantly, probe 1 could help detect H2S efficiently by a distinct color response as a visible detection agent. Probe 1 reacted with various concentrations of H2S (0-200 μM), and the detection limit for H2S was 0.10 μM. Particularly, probe 1 can be applied as a sensor to detect H2S accurately in wine samples.

| S-EPMC6348852 | biostudies-literature

Cell-trappable fluorescent probes for endogenous hydrogen sulfide signaling and imaging H2O2-dependent H2S production.

Project description:Hydrogen sulfide (H2S) is a reactive small molecule generated in the body that can be beneficial or toxic owing to its potent redox activity. In living systems, disentangling the pathways responsible for H2S production and their physiological and pathological consequences remains a challenge in part due to a lack of methods for monitoring changes in endogenous H2S fluxes. The development of fluorescent probes with appropriate selectivity and sensitivity for monitoring production of H2S at biologically relevant signaling levels offers opportunities to explore its roles in a variety of systems. Here we report the design, synthesis, and application of a family of azide-based fluorescent H2S indicators, Sulfidefluor-4, Sulfidefluor-5 acetoxymethyl ester, and Sulfidefluor-7 acetoxymethyl ester, which offer the unique capability to image H2S generated at physiological signaling levels. These probes are optimized for cellular imaging and feature enhanced sensitivity and cellular retention compared with our previously reported molecules. In particular, Sulfidefluor-7 acetoxymethyl ester allows for direct, real-time visualization of endogenous H2S produced in live human umbilical vein endothelial cells upon stimulation with vascular endothelial growth factor (VEGF). Moreover, we show that H2S production is dependent on NADPH oxidase-derived hydrogen peroxide (H2O2), which attenuates VEGF receptor 2 phosphorylation and establishes a link for H2S/H2O2 crosstalk.

| S-EPMC3645565 | biostudies-literature

Trapping hydrogen sulfide (H₂S) with diselenides: the application in the design of fluorescent probes.

Project description:Here we report a unique reaction between phenyl diselenide-ester substrates and H2S to form 1,2-benzothiaselenol-3-one. This reaction proceeded rapidly under mild conditions. Thiols could also react with the diselenide substrates. However, the resulted S-Se intermediate retained high reactivity toward H2S and eventually led to the same cyclized product 1,2-benzothiaselenol-3-one. Based on this reaction two fluorescent probes were developed and showed high selectivity and sensitivity for H2S. The presence of thiols was found not to interfere with the detection process.

| S-EPMC4372083 | biostudies-literature

Chemiluminescent detection of enzymatically produced hydrogen sulfide: substrate hydrogen bonding influences selectivity for H2S over biological thiols.

Project description:Hydrogen sulfide (H2S) is now recognized as an important biological regulator and signaling agent that is active in many physiological processes and diseases. Understanding the important roles of this emerging signaling molecule has remained challenging, in part due to the limited methods available for detecting endogenous H2S. Here we report two reaction-based ChemiLuminescent Sulfide Sensors, CLSS-1 and CLSS-2, with strong luminescence responses toward H2S (128- and 48-fold, respectively) and H2S detection limits (0.7 ± 0.3, 4.6 ± 2.0 μM, respectively) compatible with biological H2S levels. CLSS-2 is highly selective for H2S over other reactive sulfur, nitrogen, and oxygen species (RSONS) including GSH, Cys, Hcy, S2O3(2–), NO2(–), HNO, ONOO(–), and NO. Despite its similar chemical structure, CLSS-1 displays lower selectivity toward amino acid-derived thiols than CLSS-2. The origin of this differential selectivity was investigated using both computational DFT studies and NMR experiments. Our results suggest a model in which amino acid binding to the hydrazide moiety of the luminol-derived probes provides differential access to the reactive azide in CLSS-1 and CLSS-2, thus eroding the selectivity of CLSS-1 for H2S over Cys and GSH. On the basis of its high selectivity for H2S, we used CLSS-2 to detect enzymatically produced H2S from isolated cystathionine γ-lyase (CSE) enzymes (p < 0.001) and also from C6 cells expressing CSE (p < 0.001). CLSS-2 can readily differentiate between H2S production in active CSE and CSE inhibited with β-cyanoalanine (BCA) in both isolated CSE enzymes (p < 0.005) and in C6 cells (p < 0.005). In addition to providing a highly sensitive and selective reaction-based tool for chemiluminescent H2S detection and quantification, the insights into substrate–probe interactions controlling the selectivity for H2S over biologically relevant thiols may guide the design of other selective H2S detection scaffolds.

| S-EPMC3868629 | biostudies-literature

Direct Comparison of Triggering Motifs on Chemiluminescent Probes for Hydrogen Sulfide Detection in Water.

Project description:Hydrogen sulfide (H2S) is an important biomolecule and significant efforts have focused on developing chemical tools to aid different biological investigations. Of such tools, there are relatively few chemiluminescent or bioluminescent methods for H2S detection. Here we report two dioxetane-based chemiluminescent probes for H2S detection. With these probes, we directly compare the probe response to H2S-mediated azide reduction and nucleophilic displacement of 2,4-dinitrophenyl motifs and demonstrate that the SNAr cleavage of the DNP group results in a larger response and greater stability in water.

| S-EPMC8765743 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data