Hydrogen Peroxide‐Responsive Triggers Based on Borinic Acids: Molecular Insights into the Control of Oxidative Rearrangement

Gatin-Fraudet, Blaise; Pucher, Mathilde; Saux, Thomas Le; Doisneau, Gilles; Bourdreux, Yann; Jullien, Ludovic; Vauzeilles, Boris; Guianvarc’h, Dominique; Urban, Dominique

doi:10.1002/chem.202201543

Cited by 4 publications

(4 citation statements)

References 72 publications

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“…All three oxygen reactive species (hypochlorous acid, hydrogen peroxide, and peroxynitrite) can cleave the arylboronic acid trigger, which acts as a receptor for photoinduced electron transfer in the buffer. The phenylboronic acid cleaved and formed a phenol derivative that exhibited intramolecular charge transfer (ICT) depending on pH and other microenvironments [ 45 ]. For a systematic study, a time-dependent kinetics reaction was recorded by monitoring at 400 nm the maximum absorbance in UV spectra for 80 min after adding 100 µM H 2 O 2 and HOCl ( Figures S2 and S3 ).…”

Section: Photophysical Propertiesmentioning

confidence: 99%

A Ratiometric Fluorescent Probe for Hypochlorite and Lipid Droplets to Monitor Oxidative Stress

et al. 2023

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Mitochondria are valuable subcellular organelles and play crucial roles in redox signaling in living cells. Substantial evidence proved that mitochondria are one of the critical sources of reactive oxygen species (ROS), and overproduction of ROS accompanies redox imbalance and cell immunity. Among ROS, hydrogen peroxide (H2O2) is the foremost redox regulator, which reacts with chloride ions in the presence of myeloperoxidase (MPO) to generate another biogenic redox molecule, hypochlorous acid (HOCl). These highly reactive ROS are the primary cause of damage to DNA (deoxyribonucleic acid), RNA (ribonucleic acid), and proteins, leading to various neuronal diseases and cell death. Cellular damage, related cell death, and oxidative stress are also associated with lysosomes which act as recycling units in the cytoplasm. Hence, simultaneous monitoring of multiple organelles using simple molecular probes is an exciting area of research that is yet to be explored. Significant evidence also suggests that oxidative stress induces the accumulation of lipid droplets in cells. Hence, monitoring redox biomolecules in mitochondria and lipid droplets in cells may give a new insight into cell damage, leading to cell death and related disease progressions. Herein, we developed simple hemicyanine-based small molecular probes with a boronic acid trigger. A fluorescent probe AB that could efficiently detect mitochondrial ROS, especially HOCl, and viscosity simultaneously. When the AB probe released phenylboronic acid after reacting with ROS, the product AB–OH exhibited ratiometric emissions depending on excitation. This AB–OH nicely translocates to lysosomes and efficiently monitors the lysosomal lipid droplets. Photoluminescence and confocal fluorescence imaging analysis suggest that AB and corresponding AB–OH molecules are potential chemical probes for studying oxidative stress.

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Section: Photophysical Propertiesmentioning

confidence: 99%

A Ratiometric Fluorescent Probe for Hypochlorite and Lipid Droplets to Monitor Oxidative Stress

et al. 2023

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“…134 Recent follow-up work detailed the synthesis of a more general trigger derivative that was further modified to overcome challenges related to the regioselectivity of oxidative deprotection. 136 Another direction is in catalytic activity-based sensing where one uncaging event can lead to multiple signal outputs. This strategy is highlighted by elegant work from Shabat and colleagues on self-immolative polymer scaffolds that can be uncaged by a single boronate oxidation or systems by Phillips that self-sustain peroxide consumption and generation for continuous detection.…”

Section: T H Imentioning

confidence: 99%

“…The reported borinic-acid-based coumarin was selective for H 2 O 2 over other ROS and exhibited a significantly faster turn-on response in live COS7 gp91/p22 . Recent follow-up work detailed the synthesis of a more general trigger derivative that was further modified to overcome challenges related to the regioselectivity of oxidative deprotection . Another direction is in catalytic activity-based sensing where one uncaging event can lead to multiple signal outputs.…”

Section: Outlook and Future Directionsmentioning

confidence: 99%

Activity-Based Sensing for Chemistry-Enabled Biology: Illuminating Principles, Probes, and Prospects for Boronate Reagents for Studying Hydrogen Peroxide

Messina

Quargnali

Chang

2022

ACS Bio Med Chem Au

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Activity-based sensing (ABS) offers a general approach that exploits chemical reactivity as a method for selective detection and manipulation of biological analytes. Here, we illustrate the value of this chemical platform to enable new biological discovery through a case study in the design and application of ABS reagents for studying hydrogen peroxide (H2O2), a major type of reactive oxygen species (ROS) that regulates a diverse array of vital cellular signaling processes to sustain life. Specifically, we summarize advances in the use of activity-based boronate probes for the detection of H2O2 featuring high molecular selectivity over other ROS, with an emphasis on tailoring designs in chemical structure to promote new biological principles of redox signaling.

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“…1B). 35 Graham and co-workers showed that neighboring functionality can dramatically change arylboronic oxidation rates. 30 For instance, o-carboxyphenylboronic acid cyclizes to a boronolactone, which slows its H2O2-mediated oxidation by more than 5-orders of magnitude (Fig.…”

mentioning

confidence: 99%

A Diazaborine-Based Fluorescent Probe Tracks Endogenously Produced Peroxynitrite in Live Cells

Haggett

Domaille²

2022

Preprint

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We present the synthesis, properties, and imaging applications of Peroxynitrite Probe-1 (PNP-1), a novel organoboron-based probe for selective peroxynitrite (ONOO-) imaging in live cells. PNP-1 features a diazaborine-based reaction motif that provides excellent discrimination between H2O2 and ONOO-, solving a persistent challenge of organoboron-based fluorescent probes for oxidative metabolite imaging. We demonstrate the utility of PNP-1 to detect endogenously produced ONOO- in live RAW 264.7 macrophages, with probe selectivity confirmed by inhibition of NADPH oxidases and nitric oxide synthase, the requisite enzy-matic machinery for ONOO- production. Beyond the direct application of PNP-1, our results reveal that diazaborines are a modular reaction motif for selective ONOO- reactivity, positioning them for incorporation into other ONOO--specific chemical biology tools.

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Hydrogen Peroxide‐Responsive Triggers Based on Borinic Acids: Molecular Insights into the Control of Oxidative Rearrangement

Abstract: Supporting information for this article is given via a link at the end of the document.

Cited by 4 publications

References 72 publications

A Ratiometric Fluorescent Probe for Hypochlorite and Lipid Droplets to Monitor Oxidative Stress

A Ratiometric Fluorescent Probe for Hypochlorite and Lipid Droplets to Monitor Oxidative Stress

Activity-Based Sensing for Chemistry-Enabled Biology: Illuminating Principles, Probes, and Prospects for Boronate Reagents for Studying Hydrogen Peroxide

A Diazaborine-Based Fluorescent Probe Tracks Endogenously Produced Peroxynitrite in Live Cells

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