Small-molecule luminescent probes for the detection of cellular oxidizing and nitrating species

Zielonka, Jacek; Kalyanaraman, Balaraman

doi:10.1016/j.freeradbiomed.2018.03.032

Cited by 64 publications

(67 citation statements)

References 254 publications

(224 reference statements)

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“…The relative increase in the yield of the phenolic product in the case of oMitoPh 18 OH was higher than in case of oMitoPh 16 OH, which we attribute to the presence of small amounts of oMitoPh 16 OH but not oMitoPh 18 OH in the probe stock solution. The representative LC-MS chromatograms are shown for both H2 16 O2 and H2 18 O2, with increased concentrations of NaHCO3 are shown in Fig. 6d,e.…”

Section: Peroxymonocarbonatementioning

confidence: 60%

“…6bc). This effect was observed for both H2 16 O2 and H2 18 O2, when monitoring the 16 O-or 18 O-phenolic products, respectively (Fig. 6c).…”

Section: Peroxymonocarbonatementioning

confidence: 74%

“…5). The product detected in the presence of H2 16 O2 showed the molecular mass of oMitoPh 16 OH (m/z = 369); in the presence of H2 18 O2, the product had a molecular mass of 371 ( Fig. 5b), attributed to oMitoPh 18 OH.…”

Section: Hydrogen Peroxidementioning

confidence: 99%

“…H2O2 oxidizes the phenylboronate substrate into a phenoxyboronate intermediate that, upon hydrolysis, yields the phenolic product and boric acid. To determine if the phenolic oxygen atom derives from H2O2 or water, we performed the oxidation of oMitoPhB(OH)2 by H2 16 O2 in H2 18 O and by H2 18 O2 in H2 16 O (Fig. 5).…”

Section: Hydrogen Peroxidementioning

confidence: 99%

“…The product of the reaction is a phenol (or alcohol), which may undergo chlorination in the presence of excess HOCl (47,51,57). To determine the source of the oxygen atom during the conversion of oMitoPhB(OH)2 into oMitoPhOH, we generated H 16 OCl and H 18 OCl in situ from myeloperoxidase (MPO)-catalyzed oxidation of chloride anions by H2 16 O2 and H2 18 O2, respectively (Fig. 7a).…”

Section: Hypochloritementioning

confidence: 99%

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Tracking isotopically labeled oxidants using boronate-based redox probes

Ríos

Radí

Kalyanaraman

et al. 2020

Journal of Biological Chemistry

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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.

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Section: Peroxymonocarbonatementioning

confidence: 60%

“…6bc). This effect was observed for both H2 16 O2 and H2 18 O2, when monitoring the 16 O-or 18 O-phenolic products, respectively (Fig. 6c).…”

Section: Peroxymonocarbonatementioning

confidence: 74%

Section: Hydrogen Peroxidementioning

confidence: 99%

Section: Hydrogen Peroxidementioning

confidence: 99%

Section: Hypochloritementioning

confidence: 99%

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Tracking isotopically labeled oxidants using boronate-based redox probes

Ríos

Radí

Kalyanaraman

et al. 2020

Journal of Biological Chemistry

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Peptide Vectors Carry Pyrene to Cell Organelles Allowing Real‐Time Quantification of Free Radicals in Mitochondria by Time‐Resolved Fluorescence Microscopy

et al. 2021

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Real‐time quantification of reactive nitrogen and oxygen species (ROS) in cells is of paramount importance as they are essential for cellular functions. Their excessive formation contributes to the dysfunction of cells and organisms, ultimately leading to cell death. As ROS are mostly produced in the mitochondria, we have synthesized a fluorescent probe able to reach this organelle to detect and quantify, in real time, the variation of ROS by time‐resolved microfluorimetry. The new probes are based on the long fluorescence lifetime of pyrene butyric acid (PBA). Two PBA isomers, attached at their 1‐ or 2‐positions to a peptide vector to target mitochondria, were compared and were shown to allow the measurement of free radical species and oxygen, but not non‐radical species such as H2O2.

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Theoretical study on oxidation mechanism of fluorescent probe, coumarin‐7‐pinacolboronate by various reactive oxygen species

Guo,

Leng,

Liu

et al. 2023

J of Physical Organic Chem

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Hydrogen peroxide (H2O2) as relatively stable reactive oxygen species gains considerable attention because it can regulate physiological and pathological processes. In order to better detect H2O2, fluorescent probes were widely applied. Over the past 20 years, a great deal of boronate‐based fluorescent molecular probes appeared due to relatively simple oxidation reaction. However, the reaction mechanisms that boronate derivatives were converted into fluorescent product by H2O2 are poorly studied. In this paper, taking coumarin‐7‐pinacolboronate (CBU) as an example, the oxidation mechanism of boronate‐based probes by various reactive oxygen species was studied by theoretical calculations. The results found that (1) the chemical reaction mechanisms are nearly identical for the reactions of CBU with hydrogen peroxide, hypochlorous acid, peroxynitrite, and tyrosine hydroperoxide, respectively. (2) There is not radical intermediate during the reaction. (3) The different reactive oxygen species has a strong influence on rate limiting step and reaction rate.

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Small-molecule luminescent probes for the detection of cellular oxidizing and nitrating species

Cited by 64 publications

References 254 publications

Tracking isotopically labeled oxidants using boronate-based redox probes

Tracking isotopically labeled oxidants using boronate-based redox probes

Peptide Vectors Carry Pyrene to Cell Organelles Allowing Real‐Time Quantification of Free Radicals in Mitochondria by Time‐Resolved Fluorescence Microscopy

Theoretical study on oxidation mechanism of fluorescent probe, coumarin‐7‐pinacolboronate by various reactive oxygen species

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