Fluorescent Probe For Hydrogen Peroxide Research Articles

A new lysosome-targeted fluorescent probe for hydrogen peroxide based on a benzothiazole derivative.

As an important member of reactive oxygen species, hydrogen peroxide (H2O2) plays a key role in oxidative stress and cell signaling. Abnormal levels of H2O2 in lysosomes can induce damage or even loss of lysosomal function, leading to certain diseases. Therefore, real-time monitoring of H2O2 in lysosomes is very important. In this work, we designed and synthesized a novel lysosome-targeted fluorescent probe for H2O2-specific detection based on a benzothiazole derivative. A morpholine group was used as a lysosome-targeted unit and a boric acid ester was chosen as the reaction site. In the absence of H2O2, the probe exhibited very weak fluorescence. In the presence of H2O2, the probe showed an increased fluorescence emission. The fluorescence intensity of the probe for H2O2 displayed a good linear relationship in the concentration range of H2O2 from 8.0×10-7 to 2.0×10-4 mol·L-1. The detection limit was estimated to be 4.6×10-7 mol·L-1 for H2O2. The probe possessed high selectivity, good sensitivity and short response time for the detection of H2O2. Moreover, the probe had almost no cytotoxicity and had been successfully applied to confocal imaging of H2O2 in lysosomes of A549 cells. These results illustrated that the developed fluorescent probe in this study could provide a good tool for the determination of H2O2 in lysosomes.

A Novel Fluorescent Probe for Hydrogen Peroxide and Its Application in Bio-Imaging.

Hydrogen peroxide (H2O2) plays an important role in the human body and monitoring its level is meaningful due to the relationship between its level and diseases. A fluorescent sensor (CMB) based on coumarin was designed and its ability for detecting hydrogen peroxide by fluorescence signals was also studied. The CMB showed an approximate 25-fold fluorescence enhancement after adding H2O2 due to the interaction between the CMB and H2O2 and had the potential for detecting physiological H2O2. It also showed good biocompatibility and permeability, allowing it to penetrate cell membranes and zebrafish tissues, thus it can perform fluorescence imaging of H2O2 in living cells and zebrafish. This probe is a promising tool for monitoring the level of H2O2 in related physiological and pathological research.

Development of a coumarin-based fluorescent probe for hydrogen peroxide based on the Payne/Dakin tandem reaction

Hydrogen peroxide (H2O2) is associated with many physiological and pathological processes in biological systems. Here, we report 7-diethylamino-3-formyl-coumarin (Cou-CHO) as a turn-on fluorescent probe for H2O2. The proposed probe employs a tandem Payne/Dakin reaction to convert the electron-withdrawing aldehyde to the electron-donating hydroxyl group, thus hindering the formation of twisted intramolecular charge transfer (TICT) state of 7-diethylaminocoumarin, and thereby resulting in a fluorescence turn-on response. Cou-CHO features high specificity, excellent sensitivity and fast response toward H2O2. In particular, Cou-CHO enables the direct visualization of basal and endogenously produced H2O2 in living cells. The results demonstrate that the tandem Payne/Dakin reaction can provide a new choice to develop H2O2-selective probes.

Research Progress in Mitochondrial Targeting Fluorescent Probes for Hydrogen Peroxide

Research Progress in Mitochondrial Targeting Fluorescent Probes for Hydrogen Peroxide

Mitochondria and lysosome-targetable fluorescent probes for hydrogen peroxide.

Hydrogen peroxide (H2O2), as a key member of the reactive oxygen species (ROS), has a certain regulatory effect on many physiological processes, such as cell proliferation, differentiation and migration. However, abnormal production of H2O2 can cause diseases including cancer, Alzheimer's disease, cardiovascular disease, and so on. Therefore, it is important to detect changes in H2O2 at the subcellular level. In recent years, many fluorescent probes for H2O2 have been developed and used in living cells. In this review, we introduce some typical fluorescent probes for H2O2 with mitochondrial and lysosomal targeting. This review contains targeting strategies, detection mechanisms, optical characteristics and cell imaging of these probes.

Lipid Droplet‐Targetable Fluorescence Guided Photodynamic Therapy of Cancer Cells with an Activatable AIE‐Active Fluorescent Probe for Hydrogen Peroxide

AbstractFluorescence guided photodynamic therapy (FL‐PDT) offers the great opportunity for realizing personalized medicine in the treatment of cancer. Aggregation‐induced emission luminogens (AIEgens) with efficient emission and reactive oxygen species (ROS) generation even in the aggregated state are the ideal FL‐PDT photosensitizers to overcome the quenched fluorescence and ROS that traditional photosensitizers faced in PDT. Moreover, considering the higher levels of H2O2 in cancer cells than in normal cells and the fact that lipid droplet (LD) accumulation correlates to the enhanced survival rate of cancer cells in hypoxic conditions, it will be very interesting and rewarding to develop a LD‐targeted, H2O2 activatable AIE‐active photosensitizer for FL‐PDT. Thereafter, a LD‐targeted fluorescent probe TPECNPB is fabricated for H2O2‐activatable fluorescence guided PDT of cancer cells. AIE‐active TPECNPB exhibits the unique features of large Stokes shift (175 nm), superior photostability, and excellent selectivity toward H2O2. TPECNPB is able to selectively accumulate in LD and is activated by endogenous H2O2 for light‐up bioimaging in live MCF‐7 cells. In addition, H2O2‐activatable singlet oxygen generation and PDT of cancer cells has also been successfully implemented with TPECNPB. These prominent parameters would make TPECNPB a powerful toolbox for H2O2‐activatable and LD‐targetable fluorescence guided PDT of cancer cells.

Ratio fluorescent hybrid probe for visualized fluorescence detection of H2O2in vitro and in vivo

A silicon oxide quantum dots (Si-O QDs) and Ag nanoclusters hybrid nanosensing probe with dual-emission and small nanocrystals that acts as an “off-on” ratio fluorescent probe for hydrogen peroxide (H2O2) detection was developed. The probe was used to measure the H2O2 concentration generated by mitochondria in vitro via recording the I455/I680 fluorescence ratio. Furthermore, this hybrid probe was applied to monitor the wound-induced H2O2 in lettuce leaf, and realized the visualized fluorescence qualitative detection H2O2in vivo via laser scanning confocal microscope. The working mechanism of the probe is also investigated. Inner filter effect (IFE) estimation, Fourier transform infrared (FTIR) spectra and high-resolution transmission electron microscopy (HRTEM) images were applied to study the quenching mechanism and recovering reason of Si-O QDs fluorescence. The results show that the blue fluorescence of Si-O QDs can be quenched by Ag NCs via the IFE and fluorescent resonance energy transfer (FRET) effect. After adding H2O2, the surface groups of Ag NCs was changed and the IFE and FRET effects between the Si-O QDs and Ag NCs are disabled, thus the quenched Si-O QDs luminescence can be regularly recovered.

Organelle targetable fluorescent probes for hydrogen peroxide

Hydrogen peroxide (H2O2), as important products of oxygen metabolism, plays an important role in many biological processes, such as immune responses and cellular signal transduction. However, abnormal production of H2O2 can damage cellular biomolecules, which was closely associated with many diseases. Thus, it is urgent to monitor the level change of H2O2 in living cells, particularly at subcellular levels. Toward this end, a wide variety of H2O2 fluorescent probes have been designed, developed and applied for imaging of H2O2 in subcellular levels. In this review, we highlight the representative cases of H2O2 fluorescent probes with mitochondria, nuclei and lysosomes-targetable ability. The review contains organelle target strategies, structures, fluorescence behavior and biological applications of these probes.

A FRET-based fluorescent probe for hydrogen peroxide based on the use of carbon quantum dots conjugated to gold nanoclusters.

In the Fenton reaction, ferrous ion acts as a catalyst and reacts with hydrogen peroxide (H2O2) to produce hydroxy radicals (·OH) and hydroperoxy radicals (·OOH). Both have much stronger oxidization ability than H2O2. A fluorescent probe for H2O2 is described here that was obtained by covalent conjugation of carbon quantum dots to gold nanoclusters (AuNCs). The conjugate, under 360nm photoexcitation, displays dual (blue and red) emission, with peaks located at 450 and 640nm. When introducing ·OH radicals via the Fenton reaction, the fluorescence intensities of both the CQDs and the AuNCs are decreased. The ratio of the fluorescence at the two peaks is related to the concentration of H2O2 in the 1.25nM to 10μM concentration range, and the detection limit is 0.16 nM. The probe was applied to the determination of H2O2 in milk and toothpaste and to cell imaging. Graphical abstract Schematic diagram of the FRET-based fluorescent probe and enhanced performance of hydrogen peroxide detection via Fenton reaction. The fluorescence intensity of CQD-AuNCs nanoaster was decreased as introducing H2O2 to the probe, and can be applied to the determination of milk and toothpaste and cells imaging.

An ICT‐Based Mitochondria‐Targeted Fluorescent Probe for Hydrogen Peroxide with a Large Turn‐On Fluorescence Signal

AbstractAn ICT‐based mitochondria‐targeted fluorescent probe Mito‐NP was designed and synthesized for the detection of H2O2, with radical fluorescence intensity changes (up to 120‐fold) and a large Stokes shift (93 nm) in aqueous solution. There was good linear relationship (R2=0.9983) between the concentration of H2O2 in the range of 0 to 100 μM and the fluorescence intensity at 553 nm, with a low detection limit of 0.25 μM (S/N=3). Mito‐NP could also visualize enzymatically generated H2O2. Furthermore, the probe could detect endogenous H2O2 with good mitochondria targeting ability in living cells and could also detect the change in H2O2 levels during mitochondria‐oriented apoptosis.Introduction

Gold nanocluster-based ratiometric fluorescent probes for hydrogen peroxide and enzymatic sensing of uric acid

A method is described for ratiometric fluorometric assays of H2O2by using two probes that have distinct response profiles. Under the catalytic action of ferrous ion, the 615nm emission of protein-stabilized gold nanoclusters (under 365nm photoexcitation) is quenched by H2O2, while an increased signal is generated with a peak at 450nm by oxidizing coumarin with the H2O2/Fe(II) system to form a blue emitting fluorophore. These decrease/increase responses give a ratiometric signal. The ratio of the fluorescences at the two peaks are linearly related to the concentration of H2O2 in the range from 0.05 to 10μM, with a 7.7nM limit of detection. The detection scheme was further coupled to the urate oxidase catalyzed oxidation of uric acid which proceeds under the formation of H2O2. This method provides an simple and effective means for the construction of ratiometric fluorometric (enzymatic) assays that involve the detection of H2O2. Graphical abstract Under catalysis byferrous ion, hydrogen peroxide quenches the luminescence of gold nanoclusters (AuNCs) and oxidizes coumarin into a fluorescent derivative, which rendered fluorescence ON and OFF at two distinct wavelengths for ratiometric measurements.

苦味酸介导CdSe/ZnS量子点用于水环境双氧水的测定

苦味酸介导CdSe/ZnS量子点用于水环境双氧水的测定

An ESIPT-based mitochondria-targeted ratiometric and NIR-emitting fluorescent probe for hydrogen peroxide and its bioimaging in living cells

A mitochondria-targetable ratiometric fluorescent probe, HBTPB, has been developed for the detection of H2O2 with a near infrared (NIR) emission and a large Stokes shift (357 nm). Probe HBTPB displays high selectivity toward H2O2 over other reactive oxygen/nitrogen species (ROS/RNS), biological thiols and anions. The detection limit of this probe is as low as 5.9 × 10−7 M. The sensing process confirmed by NMR and mass spectral analysis shows that the addition of H2O2 to the solution of HBTPB triggers an oxidative hydrolysis and a subsequent elimination reaction undergoes to release an ESIPT (excited-state intramolecular proton transfer) featured fluorescent dye. Probe HBTPB is cell permeable and has been applied to sense exogenous and endogenous H2O2 in living A549 cells.

A mitochondria-targeted colorimetric and ratiometric fluorescent probe for hydrogen peroxide with a large emission shift and bio-imaging in living cells

A novel mitochondria-targeted fluorescent probe compound 1 for H2O2 has constructed based on a coumarin as the fluorophore and a boronate moiety as the reaction site, which showed colorimetric and ratiometric fluorescence dual response to H2O2. This probe displayed a large blue-shifted in emission wavelength (105nm) with two well-resolved emission bands toward hydrogen peroxide. The compound 1 can be quantitative, good selective and sensitive recognition to H2O2 with low detection limit (10nM). The sensing mechanism was confirmed by H NMR and HRMS spectroscopy. The mechanism regarding the optical responses of the compound 1 toward H2O2 was also determined by density function theory (DFT) calculations. Moreover, the probe could be used for determining H2O2 in living cells by ratiometric fluorescence imaging with excellent mitochondrial targeting.

A Fluorescent Probe for Hydrogen Peroxide in Vivo Based on the Modulation of Intramolecular Charge Transfer.

Endogenous hydrogen peroxide in vivo is related to many diseases, including cancer, diabetes, cardiovascular disease, and neurodegenerative disorders. Although many probes for detection of H2O2 have been explored, rapid response probes are still expected for in vivo application. Here, a new probe (PAM-BN-PB) was designed based on an intramolecular charge transfer (ICT) process with three parts: phenanthroimidazole, benzonitrile, and phenyl boronate. By modulation ICT process of PAM-BN-PB, H2O2 in solution systems can be detected with good selectivity. The exogenous and endogenous H2O2 in normal living cells, ischemia-reperfusion injury cells, and animals all can be imaged by PAM-BN-PB.

A highly selective fluorescent probe for hydrogen peroxide and its applications in living cells

Abstract A turn-on fluorescent probe ACR {6′-[2-(azidomethyl)benzoyl]-7′-chloro- N,N -diethylrhodol} for selective detection of H 2 O 2 was developed. An ester bond was broken by the nucleophilic substitution of H 2 O 2 which released strong fluorescence. Probe ACR was proved to be made up of three essential parts, chlorine atom, azide group and an active carbonyl. This probe showed high selectivity for H 2 O 2 and a linear fluorescence intensity enhancement with a wide range of concentrations of H 2 O 2 . Fluorescence imaging experiments in HeLa cells indicated its potential to image H 2 O 2 in biological systems.

Sulfur-doped carbon quantum dots and derived 3D carbon nanoflowers are effective visible to near infrared fluorescent probes for hydrogen peroxide

Near-infrared photoluminescence is intrinsic only to a minority of carbonaceous nanomaterials. Longwave fluorescence is, however, well suited for bio-sensing and bio-imaging owing to the low autofluorescence and low absorbance by biomatter. The authors describe here sulfur doped carbon quantum dots (S-CQDs) and their derivatives (referred to as 3D carbon nanoflowers; S-CNFs). Their average diameters are 2 and 28.5 nm, respectively. They display two emission peaks, one being purple and peaking at 407 nm, the other in the near-infrared and peaking at 780 nm. Quantum yields are 4% for S-CQDs and 6.4% for S-CNFs. The nanoparticles are shown to be viable fluorescent probes for hydrogen peroxide which acts as a quencher. The 3D structure of the S-CNFs and near-infrared detection result in a better linear relationship and lower detection limits. The detection limits for H2O2 are 1.1 μM for S-CQDs, and 0.6 μM for S-CNFs. The results presented here contribute to an improved understanding on how the nanostructure and selection of wavelengths affect the sensitivity and detection limits of such probes.

Photoluminescence of MoS2 quantum dots quenched by hydrogen peroxide: A fluorescent sensor for hydrogen peroxide

By cutting MoS2 microcrystals to quantum dots (QDs) of sizes below 10 nm, the photoluminescence (PL) at ca. 450 nm can be detected easily due to the quantum confinement effects across the 2D planes. The PL is stable under continuous irradiation of UV light but gradually quenches when treated with an increasing concentration of hydrogen peroxide. Time-resolved PL and Raman spectra imply that H2O2 causes the partial oxidation of MoS2 QDs. First-principles calculations reveal that the MoS2 QDs with oxygen impurity are of indirect bandgap structures showing no notable PL. And absorption spectra verify that the PL of MoS2 QDs quenched by H2O2 is attributed to the oxidation. The integrated PL intensity and H2O2 concentration show an exponential relationship in the range of 2–20 μM, suggesting that MoS2 QDs are potential fluorescent probes for hydrogen peroxide sensing in a physiological environment.

An extremely rapid-response fluorescent probe for hydrogen peroxide and its application in living cells

An extremely rapid-response fluorescent probe for H2O2was constructed for monitoring the H2O2levels in biological processes.

Rapid-response fluorescent probe for hydrogen peroxide in living cells based on increased polarity of C-B bonds.

Hydrogen peroxide (H2O2) as a reactive oxygen species (ROS) plays a crucial role in oxidative stress and signal transduction of organisms. Currently, a fluorescence probe has proven to be a powerful tool for the H2O2 analysis. However, the common problem is the slow response, causing difficulty in tracking H2O2 in situ. Herein, we describe a novel aggregation-induced emission (AIE) fluorescence probe based on increased polarity of C-B bonds that is well suited for monitoring H2O2 rapidly and selectively. Importantly, the probe was successfully applied to visualize H2O2 levels in living cells, which provides a rapid-response and highly selective fluorescence tool for monitoring of the H2O2 levels in biological process.