ArticleChemical research in toxicology2023
Boronate-Based Oxidant-Responsive Derivatives of Acetaminophen as Proinhibitors of Myeloperoxidase.
Article in Chemical research in toxicology, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Boron-Based Bioisosteres in Medicinal Chemistry: Advances in Heterocycles and Therapeutic.ChemMedChem · 2026Review
- Toward Specific Detection of Peroxynitrite─Intramolecular Cyclization of Boronobenzylated Pyridinium Probe in Chemical and Cellular Systems.Chemical research in toxicology · 2026Article
- Neutrophil Extracellular Trap-Related Gene Signatures and Molecular Clusters in Severe Influenza: Identification Through Integrative Transcriptome Analysis.Journal of immunology research · 2026Article
- Functional Group Compatibility of the Oxidation-Resistant Benzoxaborolone Pharmacophore.The Journal of organic chemistry · 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
- NiNanoscale advances · 2024Article
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8 authors.
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Abstract
Myeloperoxidase (MPO) is an important component of the human innate immune system and the main source of a strong oxidizing and chlorinating species, hypochlorous acid (HOCl). Inadvertent, misplaced, or excessive generation of HOCl by MPO is associated with multiple human inflammatory diseases. Therefore, there is a considerable interest in the development of MPO inhibitors. Here, we report the synthesis and characterization of a boronobenzyl derivative of acetaminophen (AMBB), which can function as a proinhibitor of MPO and release acetaminophen, the inhibitor of chlorination cycle of MPO, in the presence of inflammatory oxidants, i.e., hydrogen peroxide, hypochlorous acid, or peroxynitrite. We demonstrate that the AMBB proinhibitor undergoes conversion to acetaminophen by all three oxidants, with the involvement of the primary phenolic product intermediate, with relatively long half-life at pH 7.4. The determined rate constants of the reaction of the AMBB proinhibitor with hydrogen peroxide, hypochlorous acid, or peroxynitrite are equal to 1.67, 1.6 × 10
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