A coumarin-based two-photon probe for hydrogen peroxide

Zhang, Kaiming; Dou, Wei; Li, Pengxuan; Shen, Rong; Ru, Jiaxi; Liu, Wei; Cui, Yumei; Chen, Chun-Yang; Bai, Decheng

doi:10.1016/j.bios.2014.09.073

Cited by 65 publications

(17 citation statements)

References 38 publications

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“…Some fluorescent molecular sensors for H 2 O 2 have been designed based on different chemical structures − such as the hydrolysis of sulfonic esters by H 2 O 2 , the conversation of diketone to acid group, − the reaction of arylboronates to phenols, ,− and protein sensors . However, the explored probes always have some minor defects.…”

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confidence: 99%

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

et al. 2017

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Endogenous hydrogen peroxide in vivo is related to many diseases, including cancer, diabetes, cardiovascular disease, and neurodegenerative disorders. Although many probes for detection of HO 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, HO in solution systems can be detected with good selectivity. The exogenous and endogenous HO in normal living cells, ischemia-reperfusion injury cells, and animals all can be imaged by PAM-BN-PB.

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confidence: 99%

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

et al. 2017

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“…Small molecules may appear as NOX inhibitors, but act as antioxidants that scavenge O 2 •- /H 2 O 2 , inhibit HRP in the Amplex ® Red assay, or are toxic to the cells. In order to test the antioxidant potential of the inhibitors, several assays were performed using serial dilutions of compounds at constant DMSO concentration: (i) 800 μM CBA [20] was incubated in presence of 10 μM H 2 O 2 instead of cells and fluorescence measured every minute for 1 h; (ii) similarly 10 μM H 2 O 2 was incubated in presence of 25 μM Amplex ® Red and 0.05 mU/mL HRP and fluorescence measured every minute for 1 h. This assay allows to detect H 2 O 2 scavengers as well as HRP inhibitors. (iii) Another assay for determining antioxidant activity analyzes serial dilutions of compounds in the presence of free radical DPPH in methanol in transparent 96-well plates (200 μl/well).…”

Section: Methodsmentioning

confidence: 99%

Pharmacological characterization of the seven human NOX isoforms and their inhibitors

Augsburger¹,

Филиппова²,

Rasti³

et al. 2019

Redox Biology

158

154

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Background NADPH oxidases (NOX) are a family of flavoenzymes that catalyze the formation of superoxide anion radical (O 2 •- ) and/or hydrogen peroxide (H 2 O 2 ). As major oxidant generators, NOX are associated with oxidative damage in numerous diseases and represent promising drug targets for several pathologies. Various small molecule NOX inhibitors are used in the literature, but their pharmacological characterization is often incomplete in terms of potency, specificity and mode of action. Experimental approach We used cell lines expressing high levels of human NOX isoforms (NOX1-5, DUOX1 and 2) to detect NOX-derived O 2 •- or H 2 O 2 using a variety of specific probes. NOX inhibitory activity of diphenylene iodonium (DPI), apocynin, diapocynin, ebselen, GKT136901 and VAS2870 was tested on NOX isoforms in cellular and membrane assays. Additional assays were used to identify potential off target effects, such as antioxidant activity, interference with assays or acute cytotoxicity. Key results Cells expressing active NOX isoforms formed O 2 •- , except for DUOX1 and 2, and in all cases activation of NOX isoforms was associated with the detection of extracellular H 2 O 2 . Among all molecules tested, DPI elicited dose-dependent inhibition of all isoforms in all assays, however all other molecules tested displayed interesting pharmacological characteristics, but did not meet criteria for bona fide NOX inhibitors. Conclusion Our findings indicate that experimental results obtained with widely used NOX inhibitors must be carefully interpreted and highlight the challenge of developing reliable pharmacological inhibitors of these key molecular targets.

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“…Benzil is a yellow crystalline containing a diketone moiety made by oxidizing benzoin [ 44 ]. Sawaki et al have reported that benzil can transform into benzoic anhydride via a Baeyer-Villiger type reaction with H 2 O 2 in alkaline organic solvents [ 39 ].…”

Section: H 2 O 2 -Responsive Mo...mentioning

confidence: 99%

Recent Studies on Hydrogels Based on H2O2-Responsive Moieties: Mechanism, Preparation and Application

Song

You

Zhang

et al. 2022

Gels

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H2O2 is essential for cellular processes and plays a vital role in the regulation of cell signaling pathways, which can be viewed as a warning signal for many kinds of disease including cancer, cardiovascular disease, reproductive abnormalities, diabetes, and renal failure. A H2O2-responsive hydrogel (H2O2-Gel) is a promising candidate for biomedical applications because of its good biocompatibility, similarity to soft biological tissues, ease of preparation, and its ability to respond to H2O2. In this study, the H2O2-responsive moieties used to fabricate H2O2-Gels were reviewed, including thioethers, disulfide bonds, selenides, diselenium bonds, diketones, boronic, and others. Next, the preparation method of H2O2-Gel was divided into two major categories according to their reaction mechanisms: either self-crosslinking or mechanisms entailing the addition of difunctional crosslinkers. Last, the applications of H2O2-Gels were emphasized, which have been viewed as desirable candidates in the fields of drug delivery, the detection of H2O2, glucose-responsive systems, ROS scavengers, tissue engineering, and cell-encapsulation.

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A coumarin-based two-photon probe for hydrogen peroxide

Cited by 65 publications

References 38 publications

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

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

Pharmacological characterization of the seven human NOX isoforms and their inhibitors

Recent Studies on Hydrogels Based on H2O2-Responsive Moieties: Mechanism, Preparation and Application

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