Browse
Submit Data
Databases
API
Help

Dataset Information

26 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A selective, cell-permeable optical probe for hydrogen peroxide in living cells.

ABSTRACT: We present the synthesis, properties, and biological applications of Peroxyfluor-1 (PF1), a new type of optical probe for intracellular imaging of hydrogen peroxide in living biological samples. PF1 utilizes a boronate deprotection mechanism to provide unprecedented selectivity and optical dynamic range for detecting H2O2 in aqueous solution over similar reactive oxygen species including superoxide, nitric oxide, tert-butyl hydroperoxide, and hydroxyl radical. We further demonstrate the value of this reagent for biological applications by imaging changes in [H2O2] in living mammalian cells.

SUBMITTER: Chang MC

PROVIDER: S-EPMC1434465 | biostudies-literature | 2004 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

A selective, cell-permeable optical probe for hydrogen peroxide in living cells.

Chang Michelle C Y MC Pralle Arnd A Isacoff Ehud Y EY Chang Christopher J CJ

Journal of the American Chemical Society 20041201 47

We present the synthesis, properties, and biological applications of Peroxyfluor-1 (PF1), a new type of optical probe for intracellular imaging of hydrogen peroxide in living biological samples. PF1 utilizes a boronate deprotection mechanism to provide unprecedented selectivity and optical dynamic range for detecting H2O2 in aqueous solution over similar reactive oxygen species including superoxide, nitric oxide, tert-butyl hydroperoxide, and hydroxyl radical. We further demonstrate the value of ...[more]

PMID: 15563161

Similar Datasets

A red-emitting naphthofluorescein-based fluorescent probe for selective detection of hydrogen peroxide in living cells.

Project description:We report the synthesis, properties, and cellular application of Naphtho-Peroxyfluor-1 (NPF1), a new fluorescent indicator for hydrogen peroxide based on a red-emitting naphthofluorescein platform. Owing to its boronate cages, NPF1 features high selectivity for hydrogen peroxide over a panel of biologically relevant reactive oxygen species (ROS), including superoxide and nitric oxide, as well as excitation and emission profiles in the far-red region of the visible spectrum (>600nm). Flow cytometry experiments in RAW264.7 macrophages establish that NPF1 can report changes in peroxide levels in living cells.

| S-EPMC2590631 | biostudies-literature

A pyrene-based ratiometric fluorescent probe with a large Stokes shift for selective detection of hydrogen peroxide in living cells.

Project description:Hydrogen peroxide (H2O2) plays a significant role in regulating a variety of biological processes. Dysregulation of H2O2 can lead to various diseases. Although numerous fluorescent imaging probes for H2O2 have been reported, the development of H2O2 ratiometric fluorescent probe with large Stokes shift remains rather limited. Such probes have shown distinct advantages, such as minimized interference from environment and improved signal-to noise ratio. In this work, we reported a new pyrene-based compound Py-VPB as H2O2 fluorescent probe in vitro. The probe demonstrated ratiometric detection behavior, large Stokes shift and large emission shift. In addition, the probe showed high sensitivity and selectivity towards H2O2 in vitro. Based on these excellent properties, we successfully applied Py-VPB to the visualization of exogenous and endogenous H2O2 in living cells. Cell imaging study also showed that our probe was localized in the mitochondria. We envision that the probe can provide a useful tool for unmasking the biological roles of mitochondrial H2O2 in living systems.

| S-EPMC7591780 | biostudies-literature

A targetable fluorescent probe for imaging hydrogen peroxide in the mitochondria of living cells.

Project description:We present the design, synthesis, and biological applications of mitochondria peroxy yellow 1 (MitoPY1), a new type of bifunctional fluorescent probe for imaging hydrogen peroxide levels within the mitochondria of living cells. MitoPY1 combines a chemoselective boronate-based switch and a mitochondrial-targeting phosphonium moiety for detection of hydrogen peroxide localized to cellular mitochondria. Confocal microscopy and flow cytometry experiments in a variety of mammalian cell types show that MitoPY1 can visualize localized changes in mitochondrial hydrogen peroxide concentrations generated by situations of oxidative stress.

| S-EPMC2810491 | biostudies-literature

Spatially-resolved intracellular sensing of hydrogen peroxide in living cells.

Project description:Understanding intracellular redox chemistry requires new tools for the site-specific visualization of intracellular oxidation. We have developed a spatially-resolved intracellular sensor of hydrogen peroxide, HyPer-Tau, for time-resolved imaging in live cells. This sensor consists of a hydrogen peroxide-sensing protein tethered to microtubules. We demonstrate the use of the HyPer-Tau sensor for three applications; dose-dependent response of human cells to exogenous hydrogen peroxide, a model immune response of mouse macrophages to stimulation by bacterial toxin, and a spatially-resolved response to localized delivery of hydrogen peroxide. These results demonstrate that HyPer-Tau can be used as an effective tool for tracking changes in spatially localized intracellular hydrogen peroxide and for future applications in redox signaling.

| S-EPMC4653655 | biostudies-literature

Stimuli-responsive colorimetric and NIR fluorescence combination probe for selective reporting of cellular hydrogen peroxide.

Project description:Hydrogen peroxide (H2O2) is a key reactive oxygen species and a messenger in cellular signal transduction apart from playing a vital role in many biological processes in living organisms. In this article, we present phenyl boronic acid-functionalized quinone-cyanine (QCy-BA) in combination with AT-rich DNA (exogenous or endogenous cellular DNA), i.e., QCy-BA?DNA as a stimuli-responsive NIR fluorescence probe for measuring in vitro levels of H2O2. In response to cellular H2O2 stimulus, QCy-BA converts into QCy-DT, a one-donor-two-acceptor (D2A) system that exhibits switch-on NIR fluorescence upon binding to the DNA minor groove. Fluorescence studies on the combination probe QCy-BA?DNA showed strong NIR fluorescence selectively in the presence of H2O2. Furthermore, glucose oxidase (GOx) assay confirmed the high efficiency of the combination probe QCy-BA?DNA for probing H2O2 generated in situ through GOx-mediated glucose oxidation. Quantitative analysis through fluorescence plate reader, flow cytometry and live imaging approaches showed that QCy-BA is a promising probe to detect the normal as well as elevated levels of H2O2 produced by EGF/Nox pathways and post-genotoxic stress in both primary and senescent cells. Overall, QCy-BA, in combination with exogenous or cellular DNA, is a versatile probe to quantify and image H2O2 in normal and disease-associated cells.

| S-EPMC6054040 | biostudies-literature

A Cell-Permeable Fluorescent Prochelator Responds to Hydrogen Peroxide and Metal Ions by Decreasing Fluorescence.

Project description:Described here is the development of two boronic ester-based fluorescent prochelators, FloB (2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-4(5)-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzylidene-hydrazinocarbonyl]-benzoic acid) and FloB-SI (2-(6-hydroxy-3-oxo-3Hxanthen-9-yl)-4(5)-[2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxy)-benzylidene-hydrazinocarbonyl]-benzoic acid) that show a fluorescence response to a variety of transition metal ions only after reaction with H(2)O(2). Both prochelators' boronic ester masks are oxidized by H(2)O(2) to reveal a fluorescein-tagged metal chelator, FloS (4(5)-(2-hydroxy-benzylidenehydrazinocarbonyl)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid). Chelation of Fe(3+) or Cu(2+) elicits a 70% decrease in the emission signal of FloS, while Zn(2+), Ni(2+), and Co(2+) produce a more modest fluorescence decrease. The conversion of FloB to FloS proceeds in organic solvents, but hydrolytic decomposition of its hydrazone backbone is observed in aqueous solution. However, FloB-SI oxidizes cleanly with H(2)O(2) within 1 h in aqueous solutions to produce FloS. Fluorescence microscopy studies in HeLa cells with FloB-SI show that the sensor's fluorescence intensity remains unchanged until incubation with exogenous H(2)O(2), which results in a decreased fluorescent signal. Incubation with a competitive chelator restores the emission response, thus suggesting that FloB-SI can effectively report on a H(2)O(2)-induced increase in intracellular labilized metal.

| S-EPMC3266376 | biostudies-literature

A novel near-infrared fluorescent probe for highly selective recognition of hydrogen sulfide and imaging in living cells.

Project description:A novel near-infrared fluorescent probe (L) based on a 1,4-diethyl-1,2,3,4-tetrahydro-7H-pyrano[2,3-g]quinoxalin-7-one scaffold has been synthesized and characterized. Probe L displays highly selective and sensitive recognition to H2S over various anions and biological thiols with a large Stokes shift (125 nm) in THF/H2O (6/4, v/v, Tris-HCl 10 mM, pH = 7.4). This probe exhibits turn-on fluorescence for H2S through HS- induced thiolysis of dinitrophenyl ether. Confocal laser scanning micrographs of MCF-7 cells incubated with L confirm that L is cell-permeable and can successfully detect H2S in living cells.

| S-EPMC9081853 | biostudies-literature

Turn-on Luminescent Probe for Hydrogen Peroxide Sensing and Imaging in Living Cells based on an Iridium(III) Complex-Silver Nanoparticle Platform.

Project description:A sensitive turn-on luminescent sensor for H2O2 based on the silver nanoparticle (AgNP)-mediated quenching of an luminescent Ir(III) complex (Ir-1) has been designed. In the absence of H2O2, the luminescence intensity of Ir-1 can be quenched by AgNPs via non-radiative energy transfer. However, H2O2 can oxidize AgNPs to soluble Ag+ cations, which restores the luminescence of Ir-1. The sensing platform displayed a sensitive response to H2O2 in the range of 0-17??M, with a detection limit of 0.3??M. Importantly, the probe was successfully applied to monitor intracellular H2O2 in living cells, and it also showed high selectivity for H2O2 over other interfering substances.

| S-EPMC5566206 | biostudies-literature

Hydrogen peroxide detection with high specificity in living cells and inflamed tissues.

Project description:Hydrogen peroxide (H2O2) detection in biological systems is of significant importance, which act as critical second messenger in fundamental biological processes. Here, we report on a chemoselective fluorescent naphthylimide peroxide probe (NPP) for the H2O2 detection in vitro and in vivo. NPP is a phenylboronic acid-caged chromophore that selectively responds to H2O2 through a self-immolate mechanism. NPP exhibited high sensitivity and selectivity to H2O2 with distinctive fluorescence change due to the excellent two-photon excitation property, which permits the facile detection of inflammation produced H2O2 and offers chance to monitor the inflammatory stages in diseased cells.

| S-EPMC4966294 | biostudies-literature

A highly selective and sensitive near-infrared fluorescent probe for imaging of hydrogen sulphide in living cells and mice.

Project description:Hydrogen sulphide (H2S), the third endogenous gaseous signalling molecule, has attracted attention in biochemical research. The selective detection of H2S in living systems is essential for studying its functions. Fluorescence detection methods have become useful tools to explore the physiological roles of H2S because of their real-time and non-destructive characteristics. Herein we report a near-infrared fluorescent probe, NIR-HS, capable of tracking H2S in living organisms. With high sensitivity, good selectivity and low cytotoxicity, NIR-HS was able to recognize both the exogenous and endogenous H2S in living cells. More importantly, it realized the visualization of endogenous H2S generated in cells overexpressing cystathionine ?-synthase (CBS), one of the enzymes responsible for producing endogenous H2S. The probe was also successfully applied to detect both the exogenous and endogenous H2S in living mice. The superior sensing properties of the probe render it a valuable research tool in the H2S-related medical research.

| S-EPMC4705538 | 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