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      Boronate-Based Probes for Biological Oxidants: A Novel Class of Molecular Tools for Redox Biology

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          Abstract

          Boronate-based molecular probes are emerging as one of the most effective tools for detection and quantitation of peroxynitrite and hydroperoxides. This review discusses the chemical reactivity of boronate compounds in the context of their use for detection of biological oxidants, and presents examples of the practical use of those probes in selected chemical, enzymatic, and biological systems. The particular reactivity of boronates toward nucleophilic oxidants makes them a distinct class of probes for redox biology studies. We focus on the recent progress in the design and application of boronate-based probes in redox studies and perspectives for further developments.

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          Most cited references223

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          Hydroperoxide metabolism in mammalian organs.

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            Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications.

            Mitochondria are recognized as one of the most important targets for new drug design in cancer, cardiovascular, and neurological diseases. Currently, the most effective way to deliver drugs specifically to mitochondria is by covalent linking a lipophilic cation such as an alkyltriphenylphosphonium moiety to a pharmacophore of interest. Other delocalized lipophilic cations, such as rhodamine, natural and synthetic mitochondria-targeting peptides, and nanoparticle vehicles, have also been used for mitochondrial delivery of small molecules. Depending on the approach used, and the cell and mitochondrial membrane potentials, more than 1000-fold higher mitochondrial concentration can be achieved. Mitochondrial targeting has been developed to study mitochondrial physiology and dysfunction and the interaction between mitochondria and other subcellular organelles and for treatment of a variety of diseases such as neurodegeneration and cancer. In this Review, we discuss efforts to target small-molecule compounds to mitochondria for probing mitochondria function, as diagnostic tools and potential therapeutics. We describe the physicochemical basis for mitochondrial accumulation of lipophilic cations, synthetic chemistry strategies to target compounds to mitochondria, mitochondrial probes, and sensors, and examples of mitochondrial targeting of bioactive compounds. Finally, we review published attempts to apply mitochondria-targeted agents for the treatment of cancer and neurodegenerative diseases.
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              Free radical lipid peroxidation: mechanisms and analysis.

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                Author and article information

                Contributors
                Journal
                Front Chem
                Front Chem
                Front. Chem.
                Frontiers in Chemistry
                Frontiers Media S.A.
                2296-2646
                25 September 2020
                2020
                : 8
                : 580899
                Affiliations
                [1] 1Faculty of Chemistry, Institute of Applied Radiation Chemistry, Lodz University of Technology , Lodz, Poland
                [2] 2Department of Biophysics and Free Radical Research Center, Medical College of Wisconsin , Milwaukee, WI, United States
                [3] 3Faculty of Chemistry, Institute of Polymer and Dye Technology, Lodz University of Technology , Lodz, Poland
                Author notes

                Edited by: Giuseppe Vitiello, University of Naples Federico II, Italy

                Reviewed by: Gloria Virginia López, Universidad de la República, Uruguay; Flavia Carla Meotti, University of São Paulo, Brazil; María Lucía Piacenza, Universidad de la República, Uruguay

                *Correspondence: Adam Sikora adam.sikora@ 123456p.lodz.pl

                This article was submitted to Chemical Biology, a section of the journal Frontiers in Chemistry

                Article
                10.3389/fchem.2020.580899
                7545953
                33102447
                350d0275-1d33-48f0-b25d-594e0230c550
                Copyright © 2020 Sikora, Zielonka, Dębowska, Michalski, Smulik-Izydorczyk, Pięta, Podsiadły, Artelska, Pierzchała and Kalyanaraman.

                This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

                History
                : 07 July 2020
                : 12 August 2020
                Page count
                Figures: 12, Tables: 3, Equations: 4, References: 224, Pages: 32, Words: 21504
                Funding
                Funded by: Narodowe Centrum Nauki 10.13039/501100004281
                Funded by: American Cancer Society 10.13039/100000048
                Categories
                Chemistry
                Review

                peroxynitrite,hydrogen peroxide,hydroperoxides,hypochlorous acid,azanone,nadph oxidases,boronic acids,molecular probes

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