Sensitive detection and estimation of cell-derived peroxynitrite fluxes using fluorescein-boronate

Ríos, Natalia; Piacenza, Lucı́a; Trujillo, Madia; Martínez, Alejandra; Demicheli, Verónica; Prolo, Carolina; Álvarez, María Noel; López, Gloria V.; Radí, Rafael

doi:10.1016/j.freeradbiomed.2016.08.033

Cited by 69 publications

(61 citation statements)

References 64 publications

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“…CBA and CBE indicate a boronic acid or a boronic pinacolate ester attached to a coumarin scaffold, respectively (193). Fl-B (194), FlAmBE (192), and FBBE (205)…”

Section: Jbc Reviews: Analysis Of No ⅐ -Derived Oxidantsmentioning

confidence: 99%

“…Another mechanistic possibility for the detection of peroxynitrite involves a nucleophilic attack by the oxidant to an electrophilic functional group supported on the probe, leading to fluorescence. Different functional groups have been proposed as electrophilic centers, like activated ketones (187)(188)(189), ␣-ketoamides (190,191), and boronates (boronic acids or boronic esters) (192)(193)(194).…”

Section: Probes That React Directly With Peroxynitrite Anionmentioning

confidence: 99%

“…Boronate-based probes are successfully applied to the assessment of peroxynitrite in biological systems (192,194). Even though they were originally conceived for hydrogen peroxide detection (195,196), it was later demonstrated that boronate derivatives react considerably faster with peroxynitrite than with hydrogen peroxide (192)(193)(194)) (see below). These compounds are particularly promising due to the simplicity of their reaction with peroxynitrite and are arising as the most suitable probes for detecting and even quantifying this oxidant.…”

Section: Probes That React Directly With Peroxynitrite Anionmentioning

confidence: 99%

“…Ϫ ), amino acid hydroperoxides (ROO Ϫ ), or hypochlorite (ClO Ϫ ) are prone to react with the electrophilic center of boronates (Equation 19). The rate constant of the reaction with ONOO Ϫ is several orders of magnitude higher (k ONOOϪ ϳ10 6 , k ClOϪ 10 2 , k HCO4Ϫ 170, k ROOϪ ϳ20, and k H2O2 ϳ1-2 M Ϫ1 s Ϫ1 ) at physiological pH (193,194,199,200).…”

Section: Probes That React Directly With Peroxynitrite Anionmentioning

confidence: 99%

“…The reaction mechanism with peroxynitrite, similar to that with H 2 O 2 , involves a nucleophilic addition of ONOO Ϫ (or HOO Ϫ ) to the electrophilic boron atom generating an anionic quaternary intermediate that suffers a subsequent heterolytic cleavage at the peroxyl bond and hydrolysis giving phenol as the major nonradical end product (ϳ85-99% yield) (194,201). The phenol, appropriately derivatized, is fluorescent.…”

Section: Probes That React Directly With Peroxynitrite Anionmentioning

confidence: 99%

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Detection and quantification of nitric oxide–derived oxidants in biological systems

Möller

Ríos

Trujillo

et al. 2019

Journal of Biological Chemistry

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127

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Edited by Ruma Banerjee The free radical nitric oxide (NO ⅐) exerts biological effects through the direct and reversible interaction with specific targets (e.g. soluble guanylate cyclase) or through the generation of secondary species, many of which can oxidize, nitrosate or nitrate biomolecules. The NO ⅐-derived reactive species are typically short-lived, and their preferential fates depend on kinetic and compartmentalization aspects. Their detection and quantification are technically challenging. In general, the strategies employed are based either on the detection of relatively stable end products or on the use of synthetic probes, and they are not always selective for a particular species. In this study, we describe the biologically relevant characteristics of the reactive species formed downstream from NO ⅐ , and we discuss the approaches currently available for the analysis of NO ⅐ , nitrogen dioxide (NO 2 ⅐), dinitrogen trioxide (N 2 O 3), nitroxyl (HNO), and peroxynitrite (ONOO ؊ /ONOOH), as well as peroxynitrite-derived hydroxyl (HO ⅐) and carbonate anion (CO 3 ⅐ ؊) radicals. We also discuss the biological origins of and analytical tools for detecting nitrite (NO 2 ؊), nitrate (NO 3 ؊), nitrosyl-metal com

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“…CBA and CBE indicate a boronic acid or a boronic pinacolate ester attached to a coumarin scaffold, respectively (193). Fl-B (194), FlAmBE (192), and FBBE (205)…”

Section: Jbc Reviews: Analysis Of No ⅐ -Derived Oxidantsmentioning

confidence: 99%

Section: Probes That React Directly With Peroxynitrite Anionmentioning

confidence: 99%

Section: Probes That React Directly With Peroxynitrite Anionmentioning

confidence: 99%

Section: Probes That React Directly With Peroxynitrite Anionmentioning

confidence: 99%

Section: Probes That React Directly With Peroxynitrite Anionmentioning

confidence: 99%

See 3 more Smart Citations

Detection and quantification of nitric oxide–derived oxidants in biological systems

Möller

Ríos

Trujillo

et al. 2019

Journal of Biological Chemistry

Self Cite

127

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show abstract

Materialien mit Selektivität für oxidative Molekülspezies für die Diagnostik und Therapie

et al. 2020

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Abbildung 1. A) Krankheiten, fürdie oxidativer Stress bedeutsam ist. B) Primäre Untergruppen oxidativer Molekülspezies, ihre Entstehungsund Transformationsreaktionen und ihre Halbwertszeit. a Die Halbwertszeit der verwandten Radikale hängt von den Umgebungsbedingungen ab. Caiyan Zhao ist als Postdoktorandin Stipendiatin an der Havard Medical School. Sie wurde 2018 in physikalischer Chemie am National Center for Nanoscience and Technology,C hinese Academy of Science (China) promoviert. Dann wechselte sie zur Fuzhou University und ist dort seit 2018 Postdoktorandin. In ihren Forschungenkonzentriert sie sich auf die Entwicklung antioxidativer und multifunktionaler Nanoplattformen zur Freisetzung von Therapeutika von niedermolekularen Substanzen bis hin zu RNA fürdie Behandlung entzündlicher Erkrankungen. Jinjun Shi ist Associate Professora nder Harvard MedicalS chool und Fakultätsmitglied am Center for Nanomedicine and Department of Anesthesiology am Brigham and Women'sHospital. Er befasst sich mit Grundlagen-und angewandter Forschung im Nanomedizinbereich. Dabei geht es um eine interdisziplinäre Kombination aus Nanotechnologie, Biomaterialien, RNA-Freisetzung, Immuntherapie und antioxidativer Therapie fürb iomedizinische Anwendungen gegen Verletzungen und verschiedeneK rankheiten wie Krebs. Er wurde 2008 an der Texas A&MUniversity promoviertund arbeitete als PostdoktorandamMIT und am Brigham and Woman'sHospital. Jibin Song promovierte 2014 in Chemical and BiomedicalE ngineeringa nder Nanyang Technological University (Singapur). Danach arbeitete er als Postdoktorand bei Prof. Xiaoyuan (Shawn) Chen an den National Institutes of Health (NIH). Er wechselte 2018 zur Fuzhou University als "Min Jiang Scholar"-Professor füranalytische Chemie. Seine Forschung dreht sich vor allem um die Entwicklungv on Nanosonden fürm olekulare Bildgebung fürB ioimaging, Biosensoriku nd Wirkstoff-oder Genfreisetzung.

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In‐Cell Generation of Anticancer Phenanthridine Through Bioorthogonal Cyclization in Antitumor Prodrug Development

et al. 2021

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Pharmacological inactivation of antitumor drugs toward healthy cells is a critical factor in prodrug development. Typically, pharmaceutical chemists graft temporary moieties to existing antitumor drugs to reduce their pharmacological activity. Here, we report a platform able to generate the cytotoxic agent by intramolecular cyclization. Using phenanthridines as cytotoxic model compounds, we designed ringopened biaryl precursors that generated the phenanthridines through bioorthogonal irreversible imination. This reaction was triggered by reactive oxygen species, commonly overproduced in cancer cells, able to convert a vinyl boronate ester function into a ketone that subsequently reacted with a pendant aniline. An inactive precursor was shown to engender a cytotoxic phenanthridine against KB cancer cells. Moreover, the kinetic of cyclization of this prodrug was extremely rapid inside living cells of KB cancer spheroids so as to circumvent drug action.

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Sensitive detection and estimation of cell-derived peroxynitrite fluxes using fluorescein-boronate

Cited by 69 publications

References 64 publications

Detection and quantification of nitric oxide–derived oxidants in biological systems

Detection and quantification of nitric oxide–derived oxidants in biological systems

Materialien mit Selektivität für oxidative Molekülspezies für die Diagnostik und Therapie

In‐Cell Generation of Anticancer Phenanthridine Through Bioorthogonal Cyclization in Antitumor Prodrug Development

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