ArticleThe Journal of biological chemistry2014
Real-time measurements of amino acid and protein hydroperoxides using coumarin boronic acid.
Article in The Journal of biological chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
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Who cites it
36 citing papers in PubMed, 72 citations in OpenAlex.
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- Enhanced systemic oxidative stress response in patients with idiopathic inflammatory myopathies.Arthritis research & therapy · 2025Article
- Designing Functional and Responsive Molecules with Boronic Acids.Accounts of chemical research · 2025Article
- Small molecule probes for peroxynitrite detection.Redox biochemistry and chemistry · 2024Article
- Boronate-Based Bioactive Compounds Activated by Peroxynitrite and Hydrogen Peroxide.Redox biochemistry and chemistry · 2024Article
- Generation of singlet oxygen inside living cells: correlation between phosphorescence decay lifetime, localization and outcome of photodynamic action.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2024Article
- NADPH Oxidases: From Molecular Mechanisms to Current Inhibitors.Journal of medicinal chemistry · 2023Review
- Increased Oxidative Stress in Asthma-Relation to Inflammatory Blood and Lung Biomarkers and Airway Remodeling Indices.Biomedicines · 2022Article
- Fluorescent probes for monitoring myeloperoxidase-derived hypochlorous acid: a comparative study.Scientific reports · 2022Article
- Identification of Peroxynitrite by Profiling Oxidation and Nitration Products from Mitochondria-Targeted Arylboronic Acid.Methods in molecular biology (Clifton, N.J.) · 2021Article
- Photoreactivity of Bis-retinoid A2E Complexed with a Model Protein in Selected Model Systems.Cell biochemistry and biophysics · 2020Article
- The Effect of Antioxidants on Photoreactivity and Phototoxic Potential of RPE Melanolipofuscin Granules from Human Donors of Different Age.Antioxidants (Basel, Switzerland) · 2020Article
- Cysteine sulfenylation by CD36 signaling promotes arterial thrombosis in dyslipidemia.Blood advances · 2020Article
- Quercetin protects ARPE-19 cells against photic stress mediated by the products of rhodopsin photobleaching.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2020Article
- Tracking isotopically labeled oxidants using boronate-based redox probes.The Journal of biological chemistry · 2020Article
- Boronate-Based Probes for Biological Oxidants: A Novel Class of Molecular Tools for Redox Biology.Frontiers in chemistry · 2020Review
- Detection, identification, and quantification of oxidative protein modifications.The Journal of biological chemistry · 2019Review
- Detection and quantification of nitric oxide-derived oxidants in biological systems.The Journal of biological chemistry · 2019Review
- Lipofuscin-mediated photodynamic stress induces adverse changes in nanomechanical properties of retinal pigment epithelium cells.Scientific reports · 2018Article
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
Abstract
Hydroperoxides of amino acid and amino acid residues (tyrosine, cysteine, tryptophan, and histidine) in proteins are formed during oxidative modification induced by reactive oxygen species. Amino acid hydroperoxides are unstable intermediates that can further propagate oxidative damage in proteins. The existing assays (oxidation of ferrous cation and iodometric assays) cannot be used in real-time measurements. In this study, we show that the profluorescent coumarin boronic acid (CBA) probe reacts with amino acid and protein hydroperoxides to form the corresponding fluorescent product, 7-hydroxycoumarin. 7-Hydroxycoumarin formation was catalase-independent. Based on this observation, we have developed a fluorometric, real-time assay that is adapted to a multiwell plate format. This is the first report showing real-time monitoring of amino acid and protein hydroperoxides using the CBA-based assay. This approach was used to detect protein hydroperoxides in cell lysates obtained from macrophages exposed to visible light and photosensitizer (rose bengal). We also measured the rate constants for the reaction between amino acid hydroperoxides (tyrosyl, tryptophan, and histidine hydroperoxides) and CBA, and these values (7-23 M(-1) s(-1)) were significantly higher than that measured for H2O2 (1.5 M(-1) s(-1)). Using the CBA-based competition kinetics approach, the rate constants for amino acid hydroperoxides with ebselen, a glutathione peroxidase mimic, were also determined, and the values were within the range of 1.1-1.5 × 10(3) M(-1) s(-1). Both ebselen and boronates may be used as small molecule scavengers of amino acid and protein hydroperoxides. Here we also show formation of tryptophan hydroperoxide from tryptophan exposed to co-generated fluxes of nitric oxide and superoxide. This observation reveals a new mechanism for amino acid and protein hydroperoxide formation in biological systems.
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