Tracking isotopically labeled oxidants using boronate-based redox probes
Resumen:
Reactive oxygen and nitrogen species have been implicated in many biological processes and diseases, including immune responses, cardiovascular dysfunction, neurodegeneration, and cancer. These chemical species are short-lived in biological settings, and detecting them in these conditions and diseases requires the use of molecular probes that form stable, easily detectable, products. The chemical mechanisms and limitations of many of the currently used probes are not well-understood, hampering their effective applications. Boronates have emerged as a class of probes for the detection of nucleophilic two-electron oxidants. Here, we report the results of an oxygen-18-labeling MS study to identify the origin of oxygen atoms in the oxidation products of phenylboronate targeted to mitochondria. We demonstrate that boronate oxidation by hydrogen peroxide, peroxymonocarbonate, hypochlorite, or peroxynitrite involves the incorporation of oxygen atoms from these oxidants. We therefore conclude that boronates can be used as probes to track isotopically labeled oxidants. This suggests that the detection of specific products formed from these redox probes could enable precise identification of oxidants formed in biological systems. We discuss the implications of these results for understanding the mechanism of conversion of the boronate-based redox probes to oxidant-specific products.
| 2020 | |
|
Hydrogen peroxide Hypochlorous acid Isotope tracing Isotopic tracer Mass spectrometry (MS) Oxygen radicals; oxygen-18 Peroxymonocarbonate Peroxynitrite Reaction mechanism Reactive nitrogen species (RNS) Reactive oxygen species (ROS) Redox probes Superoxide ion Superoxide radical anion ÁCIDOS BORÓNICOS METABOLISMO ENCÉFALO MARCAJE ISOTÓPICO SONDAS MOLECULARES ISÓTOPOS DE OXÍGENO OXIDANTES |
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| Inglés | |
| Universidad de la República | |
| COLIBRI | |
| https://hdl.handle.net/20.500.12008/55805 | |
| Acceso abierto | |
| Licencia Creative Commons Atribución (CC - By 4.0) |
| _version_ | 1875692830641356800 |
|---|---|
| author | Ríos, Natalia |
| author2 | Radi, Rafael Kalyanaraman, Balaraman Zielonka, Jacek |
| author2_role | author author author |
| author_facet | Ríos, Natalia Radi, Rafael Kalyanaraman, Balaraman Zielonka, Jacek |
| author_role | author |
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| collection | COLIBRI |
| dc.contributor.filiacion.none.fl_str_mv | Ríos Natalia, Universidad de la República (Uruguay). Facultad de Medicina. Departamento de Bioquímica y Centro de Investigaciones Biomédicas Radi Rafael, Universidad de la República (Uruguay). Facultad de Medicina. Departamento de Bioquímica y Centro de Investigaciones Biomédicas Kalyanaraman Balaraman, Medical College of Wisconsin (E.E.U.U.). Department of Biophysics Zielonka Jacek, Medical College of Wisconsin (E.E.U.U.). Department of Biophysics |
| dc.creator.none.fl_str_mv | Ríos, Natalia Radi, Rafael Kalyanaraman, Balaraman Zielonka, Jacek |
| dc.date.accessioned.none.fl_str_mv | 2026-06-30T14:45:43Z |
| dc.date.available.none.fl_str_mv | 2026-06-30T14:45:43Z |
| dc.date.issued.none.fl_str_mv | 2020 |
| dc.description.abstract.none.fl_txt_mv | Reactive oxygen and nitrogen species have been implicated in many biological processes and diseases, including immune responses, cardiovascular dysfunction, neurodegeneration, and cancer. These chemical species are short-lived in biological settings, and detecting them in these conditions and diseases requires the use of molecular probes that form stable, easily detectable, products. The chemical mechanisms and limitations of many of the currently used probes are not well-understood, hampering their effective applications. Boronates have emerged as a class of probes for the detection of nucleophilic two-electron oxidants. Here, we report the results of an oxygen-18-labeling MS study to identify the origin of oxygen atoms in the oxidation products of phenylboronate targeted to mitochondria. We demonstrate that boronate oxidation by hydrogen peroxide, peroxymonocarbonate, hypochlorite, or peroxynitrite involves the incorporation of oxygen atoms from these oxidants. We therefore conclude that boronates can be used as probes to track isotopically labeled oxidants. This suggests that the detection of specific products formed from these redox probes could enable precise identification of oxidants formed in biological systems. We discuss the implications of these results for understanding the mechanism of conversion of the boronate-based redox probes to oxidant-specific products. |
| dc.format.extent.es.fl_str_mv | 12 p. |
| dc.format.mimetype.es.fl_str_mv | application/pdf |
| dc.identifier.citation.es.fl_str_mv | Ríos N, Radi R, Kalyanaraman B y otros. Tracking isotopically labeled oxidants using boronate-based redox probes. Journal of Biological Chemistry [en línea]. 2020;295(19):6665-6676 |
| dc.identifier.doi.none.fl_str_mv | 10.1074/jbc.RA120.013402 |
| dc.identifier.eissn.none.fl_str_mv | 1083-351X |
| dc.identifier.uri.none.fl_str_mv | https://hdl.handle.net/20.500.12008/55805 |
| dc.language.iso.none.fl_str_mv | en eng |
| dc.publisher.es.fl_str_mv | American Society for Biochemistry and Molecular Biology |
| dc.relation.none.fl_str_mv | Journal of Biological Chemistry. 2020;295(19):6665-6676 |
| dc.rights.license.none.fl_str_mv | Licencia Creative Commons Atribución (CC - By 4.0) |
| dc.rights.none.fl_str_mv | info:eu-repo/semantics/openAccess |
| dc.source.none.fl_str_mv | reponame:COLIBRI instname:Universidad de la República instacron:Universidad de la República |
| dc.subject.es.fl_str_mv | Hydrogen peroxide Hypochlorous acid Isotope tracing Isotopic tracer Mass spectrometry (MS) Oxygen radicals; oxygen-18 Peroxymonocarbonate Peroxynitrite Reaction mechanism Reactive nitrogen species (RNS) Reactive oxygen species (ROS) Redox probes Superoxide ion Superoxide radical anion |
| dc.subject.other.es.fl_str_mv | ÁCIDOS BORÓNICOS METABOLISMO ENCÉFALO MARCAJE ISOTÓPICO SONDAS MOLECULARES ISÓTOPOS DE OXÍGENO OXIDANTES |
| dc.title.none.fl_str_mv | Tracking isotopically labeled oxidants using boronate-based redox probes |
| dc.type.es.fl_str_mv | Artículo |
| dc.type.none.fl_str_mv | info:eu-repo/semantics/article |
| dc.type.version.none.fl_str_mv | info:eu-repo/semantics/publishedVersion |
| description | Reactive oxygen and nitrogen species have been implicated in many biological processes and diseases, including immune responses, cardiovascular dysfunction, neurodegeneration, and cancer. These chemical species are short-lived in biological settings, and detecting them in these conditions and diseases requires the use of molecular probes that form stable, easily detectable, products. The chemical mechanisms and limitations of many of the currently used probes are not well-understood, hampering their effective applications. Boronates have emerged as a class of probes for the detection of nucleophilic two-electron oxidants. Here, we report the results of an oxygen-18-labeling MS study to identify the origin of oxygen atoms in the oxidation products of phenylboronate targeted to mitochondria. We demonstrate that boronate oxidation by hydrogen peroxide, peroxymonocarbonate, hypochlorite, or peroxynitrite involves the incorporation of oxygen atoms from these oxidants. We therefore conclude that boronates can be used as probes to track isotopically labeled oxidants. This suggests that the detection of specific products formed from these redox probes could enable precise identification of oxidants formed in biological systems. We discuss the implications of these results for understanding the mechanism of conversion of the boronate-based redox probes to oxidant-specific products. |
| eu_rights_str_mv | openAccess |
| format | article |
| id | COLIBRI_aac7b7e95763eb4f26ddfd9cf2aad3b6 |
| identifier_str_mv | Ríos N, Radi R, Kalyanaraman B y otros. Tracking isotopically labeled oxidants using boronate-based redox probes. Journal of Biological Chemistry [en línea]. 2020;295(19):6665-6676 10.1074/jbc.RA120.013402 1083-351X |
| instacron_str | Universidad de la República |
| institution | Universidad de la República |
| instname_str | Universidad de la República |
| language | eng |
| language_invalid_str_mv | en |
| network_acronym_str | COLIBRI |
| network_name_str | COLIBRI |
| oai_identifier_str | oai:colibri.udelar.edu.uy:20.500.12008/55805 |
| publishDate | 2020 |
| reponame_str | COLIBRI |
| repository.mail.fl_str_mv | karina.camps@seciu.edu.uy |
| repository.name.fl_str_mv | COLIBRI - Universidad de la República |
| repository_id_str | 4771 |
| rights_invalid_str_mv | Licencia Creative Commons Atribución (CC - By 4.0) |
| spelling | Ríos Natalia, Universidad de la República (Uruguay). Facultad de Medicina. Departamento de Bioquímica y Centro de Investigaciones BiomédicasRadi Rafael, Universidad de la República (Uruguay). Facultad de Medicina. Departamento de Bioquímica y Centro de Investigaciones BiomédicasKalyanaraman Balaraman, Medical College of Wisconsin (E.E.U.U.). Department of BiophysicsZielonka Jacek, Medical College of Wisconsin (E.E.U.U.). Department of Biophysics2026-06-30T14:45:43Z2026-06-30T14:45:43Z2020Ríos N, Radi R, Kalyanaraman B y otros. Tracking isotopically labeled oxidants using boronate-based redox probes. Journal of Biological Chemistry [en línea]. 2020;295(19):6665-6676https://hdl.handle.net/20.500.12008/5580510.1074/jbc.RA120.0134021083-351XReactive oxygen and nitrogen species have been implicated in many biological processes and diseases, including immune responses, cardiovascular dysfunction, neurodegeneration, and cancer. These chemical species are short-lived in biological settings, and detecting them in these conditions and diseases requires the use of molecular probes that form stable, easily detectable, products. The chemical mechanisms and limitations of many of the currently used probes are not well-understood, hampering their effective applications. Boronates have emerged as a class of probes for the detection of nucleophilic two-electron oxidants. Here, we report the results of an oxygen-18-labeling MS study to identify the origin of oxygen atoms in the oxidation products of phenylboronate targeted to mitochondria. We demonstrate that boronate oxidation by hydrogen peroxide, peroxymonocarbonate, hypochlorite, or peroxynitrite involves the incorporation of oxygen atoms from these oxidants. We therefore conclude that boronates can be used as probes to track isotopically labeled oxidants. This suggests that the detection of specific products formed from these redox probes could enable precise identification of oxidants formed in biological systems. We discuss the implications of these results for understanding the mechanism of conversion of the boronate-based redox probes to oxidant-specific products.Submitted by Almiñana María Cecilia (marialminana@gmail.com) on 2026-06-29T21:46:00Z No. of bitstreams: 2 license_rdf: 25630 bytes, checksum: e7132498e7c1fe99f7096667baa99b25 (MD5) Tracking isotopically labeled oxidants using boronate based redox probes.pdf: 8006551 bytes, checksum: 950ef3eda533f6d36374a77261a12b7d (MD5)Approved for entry into archive by Almiñana María Cecilia (marialminana@gmail.com) on 2026-06-30T14:08:08Z (GMT) No. of bitstreams: 2 license_rdf: 25630 bytes, checksum: e7132498e7c1fe99f7096667baa99b25 (MD5) Tracking isotopically labeled oxidants using boronate based redox probes.pdf: 8006551 bytes, checksum: 950ef3eda533f6d36374a77261a12b7d (MD5)Made available in DSpace by Luna Fabiana (fabiana.luna@seciu.edu.uy) on 2026-06-30T14:45:43Z (GMT). No. of bitstreams: 2 license_rdf: 25630 bytes, checksum: e7132498e7c1fe99f7096667baa99b25 (MD5) Tracking isotopically labeled oxidants using boronate based redox probes.pdf: 8006551 bytes, checksum: 950ef3eda533f6d36374a77261a12b7d (MD5) Previous issue date: 202012 p.application/pdfenengAmerican Society for Biochemistry and Molecular BiologyJournal of Biological Chemistry. 2020;295(19):6665-6676Las obras depositadas en el Repositorio se rigen por la Ordenanza de los Derechos de la Propiedad Intelectual de la Universidad de la República.(Res. Nº 91 de C.D.C. de 8/III/1994 – D.O. 7/IV/1994) y por la Ordenanza del Repositorio Abierto de la Universidad de la República (Res. Nº 16 de C.D.C. de 07/10/2014)info:eu-repo/semantics/openAccessLicencia Creative Commons Atribución (CC - By 4.0)Hydrogen peroxideHypochlorous acidIsotope tracingIsotopic tracerMass spectrometry (MS)Oxygen radicals; oxygen-18PeroxymonocarbonatePeroxynitriteReaction mechanismReactive nitrogen species (RNS)Reactive oxygen species (ROS)Redox probesSuperoxide ionSuperoxide radical anionÁCIDOS BORÓNICOSMETABOLISMOENCÉFALOMARCAJE ISOTÓPICOSONDAS MOLECULARESISÓTOPOS DE OXÍGENOOXIDANTESTracking isotopically labeled oxidants using boronate-based redox probesArtículoinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionreponame:COLIBRIinstname:Universidad de la Repúblicainstacron:Universidad de la RepúblicaRíos, NataliaRadi, RafaelKalyanaraman, BalaramanZielonka, JacekLICENSElicense.txtlicense.txttext/plain; charset=utf-84267http://localhost:8080/xmlui/bitstream/20.500.12008/55805/5/license.txt6429389a7df7277b72b7924fdc7d47a9MD55CC-LICENSElicense_urllicense_urltext/plain; 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- Universidad de la Repúblicafalse |
| spellingShingle | Tracking isotopically labeled oxidants using boronate-based redox probes Ríos, Natalia Hydrogen peroxide Hypochlorous acid Isotope tracing Isotopic tracer Mass spectrometry (MS) Oxygen radicals; oxygen-18 Peroxymonocarbonate Peroxynitrite Reaction mechanism Reactive nitrogen species (RNS) Reactive oxygen species (ROS) Redox probes Superoxide ion Superoxide radical anion ÁCIDOS BORÓNICOS METABOLISMO ENCÉFALO MARCAJE ISOTÓPICO SONDAS MOLECULARES ISÓTOPOS DE OXÍGENO OXIDANTES |
| status_str | publishedVersion |
| title | Tracking isotopically labeled oxidants using boronate-based redox probes |
| title_full | Tracking isotopically labeled oxidants using boronate-based redox probes |
| title_fullStr | Tracking isotopically labeled oxidants using boronate-based redox probes |
| title_full_unstemmed | Tracking isotopically labeled oxidants using boronate-based redox probes |
| title_short | Tracking isotopically labeled oxidants using boronate-based redox probes |
| title_sort | Tracking isotopically labeled oxidants using boronate-based redox probes |
| topic | Hydrogen peroxide Hypochlorous acid Isotope tracing Isotopic tracer Mass spectrometry (MS) Oxygen radicals; oxygen-18 Peroxymonocarbonate Peroxynitrite Reaction mechanism Reactive nitrogen species (RNS) Reactive oxygen species (ROS) Redox probes Superoxide ion Superoxide radical anion ÁCIDOS BORÓNICOS METABOLISMO ENCÉFALO MARCAJE ISOTÓPICO SONDAS MOLECULARES ISÓTOPOS DE OXÍGENO OXIDANTES |
| url | https://hdl.handle.net/20.500.12008/55805 |