The DOI matches its Crossref record; 4 of the 4 references it cites were found in a registry or an index.
Direct oxidation of boronates by peroxynitrite: Mechanism and implications in fluorescence imaging of peroxynitrite
Open accessAbstract
In this study, we show that boronates, a class of synthetic organic compounds, react rapidly and stoichiometrically with peroxynitrite (ONOO−) to form stable hydroxy derivatives as major products. Using stopped-flow kinetic technique, we measured the second order rate constants for the reaction with ONOO−, hypochlorous acid (HOCl), and hydrogen peroxide (H2O2), and found that ONOO− reacts with 4-acetylphenylboronic acid nearly a million times (k = 1.6 × 106 M−1 s−1) faster than H2O2 (k = 2.2 M −1 s−1) and over two hundred times faster than HOCl (k = 6.2 × 103 M−1 s−1). Nitric oxide (•NO) and superoxide (O •2−) together, but not alone, oxidized boronates to the same phenolic products. Similar reaction profiles were obtained with other boronates. Results from this study will likely help develop a novel class of fluorescent probes for detection and imaging of ONOO− formed in cellular and cell-free systems.
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Cites
Peroxynitrite: biochemistry, pathophysiology and development of therapeutics
Szabó, C., Ischiropoulos, H., & Radi, R. (2007) · Nature Reviews Drug Discovery · doi:10.1038/nrd2222 · Cited by 2,134
Chemical biology of peroxynitrite: Kinetics, diffusion, and radicals
Ferrer-Sueta, G., & Radi, R. (2009) · ACS Chemical Biology · doi:10.1021/cb800279q · Cited by 776
Molecular imaging of hydrogen peroxide produced for cell signaling
Miller, E. W., Tulyathan, O., Isacoff, E. Y., & Chang, C. J. (2007) · Nature Chemical Biology · doi:10.1038/nchembio871 · Cited by 450
Mechanism of carbon dioxide-catalyzed oxidation of tyrosine by peroxynitrite
Lymar, S. V., Jiang, Q., & Hurst, J. K. (1996) · Biochemistry · doi:10.1021/bi960331h · Cited by 299
Cited by
Zielonka, J., Joseph, J., Sikora, A., Hardy, M., Ouari, O., Vasquez-Vivar, J., Cheng, G., Lopez, M., & Kalyanaraman, B. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00042 · Cited by 1,683
Self-citationUnraveling the biological roles of reactive oxygen species
Murphy, M. P., Holmgren, A., Larsson, N.-G., Halliwell, B., Chang, C. J., Kalyanaraman, B., Rhee, S. G., Thornalley, P. J., Partridge, L., Gems, D., et al. (2011) · Cell Metabolism · doi:10.1016/j.cmet.2011.03.010 · Cited by 836
Self-citationWu, L., Sedgwick, A. C., Sun, X., Bull, S. D., He, X.-P., & James, T. D. (2019) · Accounts of Chemical Research · doi:10.1021/acs.accounts.9b00302 · Cited by 665
ROS production in phagocytes: Why, when, and where?
Dupré-Crochet, S., Erard, M., & Nüβe, O. (2013) · Journal of Leukocyte Biology · doi:10.1189/jlb.1012544 · Cited by 467
Mitochondria-Targeted Small Molecule Therapeutics and Probes
Smith, R. A. J., Hartley, R. C., & Murphy, M. P. (2011) · Antioxidants & Redox Signaling · doi:10.1089/ars.2011.3969 · Cited by 399
Metadata
- Authors
- Sikora, A., Zielonka, J., Lopez, M., Joseph, J., & Kalyanaraman, B.
- Venue
- Free Radical Biology and Medicine
- Publisher
- Elsevier BV
- Published
- 2009-11
- Volume
- 47
- Issue
- 10
- Pages
- 1401-1407
- ISSN
- 0891-5849 (ISSN-L)
- OpenAlex
- W1989980805
- Cited by
- 361
- References
- 4
- FWCI
- 3.79
- Type
- journal article
- Language
- en
- Open access
- green
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- Sikora, A., Zielonka, J., Lopez, M., Joseph, J., & Kalyanaraman, B. (2009). Direct oxidation of boronates by peroxynitrite: Mechanism and implications in fluorescence imaging of peroxynitrite. Free Radical Biology and Medicine. https://doi.org/10.1016/j.freeradbiomed.2009.08.006
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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