Toward selective detection of reactive oxygen and nitrogen species with the use of fluorogenic probes – Limitations, progress, and perspectives

Dębowska, Karolina; Dębski, Dawid; Hardy, Micaël; Jakubowska, Małgorzata; Kalyanaraman, Balaraman; Marcinek, Andrzej; Michalski, Radosław; Ouari, Olivier; Sikora, Adam; Smulik, Renata; Zielonka, Jacek

doi:10.1016/j.pharep.2015.03.016

Cited by 58 publications

(64 citation statements)

References 71 publications

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“…It should be emphasized that oxidants other than H 2 O 2 (e.g., hypohalous ions and nucleophilic peroxides) can also oxidize boronates to corresponding phenols so reaction is not specific for H 2 O 2 (Chart 27). 246,276,283 …”

Section: Mitochondria-targeted Probes and Sensors For Reactive Oxymentioning

confidence: 99%

“…246,252,284–286,295,296 Use of the o -MitoPhB(OH) 2 probe should allow the production of peroxynitrite and H 2 O 2 inside mitochondria of living animals systems to be monitored, by measuring the amounts of o -MitoPhOH and cyclo - o -MitoPh products with LC-MS/MS. 286 In addition, hypohalous (HOCl) or hypobromous (HOBr)-specific products also can be formed (Chart 31).…”

Section: Mitochondria-targeted Probes and Sensors For Reactive Oxymentioning

confidence: 99%

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Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

Zielonka¹,

Joseph²,

et al. 2017

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Mitochondria are recognized as one of the most important targets for new drug design in cancer, cardiovascular, and neurological diseases. Currently, the most effective way to deliver drugs specifically to mitochondria is by covalent linking a lipophilic cation such as an alkyltriphenylphosphonium moiety to a pharmacophore of interest. Other delocalized lipophilic cations, such as rhodamine, natural and synthetic mitochondria-targeting peptides, and nanoparticle vehicles, have also been used for mitochondrial delivery of small molecules. Depending on the approach used, and the potentials of cell and mitochondrial membranes, more than 1000-fold higher mitochondrial concentration can be achieved. Mitochondrial targeting has been developed to study mitochondrial physiology and dysfunction and the interaction between mitochondria and other subcellular organelles and for treatment of a variety of diseases such as neurodegeneration and cancer. In this review, we discuss efforts to target small-molecule compounds to mitochondria for probing mitochondria function, as diagnostic tools and potential therapeutics. We describe the physicochemical basis for mitochondrial accumulation of lipophilic cations, synthetic chemistry strategies to target compounds to mitochondria, mitochondrial probes and sensors, and examples of mitochondrial targeting of bioactive compounds. Finally, we review published attempts to apply mitochondria-targeted agents for the treatment of cancer and neurodegenerative diseases.

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Section: Mitochondria-targeted Probes and Sensors For Reactive Oxymentioning

confidence: 99%

Section: Mitochondria-targeted Probes and Sensors For Reactive Oxymentioning

confidence: 99%

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

Zielonka¹,

Joseph²,

et al. 2017

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“…[3] Arylboronic acids and their esters are oxidized to phenols with ak inetic selectivity of ca. [4,5] CÀBb ond oxidation of arylboronates by ROSh as also been widely used as at rigger in programmed depolymerization, sensing amplification, drug delivery,and theragnostics. [3a] Nevertheless,c laims of selectivity for each of these ROS have been reported in solution assays and cell imaging experiments.…”

mentioning

confidence: 99%

N‐Heterocyclic Carbene Boranes as Reactive Oxygen Species‐Responsive Materials: Application to the Two‐Photon Imaging of Hypochlorous Acid in Living Cells and Tissues

et al. 2018

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N-Heterocyclic carbene (NHC) boranes undergo oxidative hydrolysis to give imidazolium salts with excellent kinetic selectivity for HOCl over other reactive oxygen species (ROS), including peroxides and peroxynitrite. Selectivity for HOCl results from the electrophilic oxidation mechanism of NHC boranes, which stands in contrast to the nucleophilic oxidation mechanism of arylboronic acids with ROS. The change in polarity that accompanies the conversion of NHC boranes to imidazolium salts can control the formation of emissive excimers, forming the basis for the design of the first fluorescence probe for ROS based on the oxidation of B-H bonds. Two-photon microscope (TPM) ratiometric imaging of HOCl in living cells and tissues is demonstrated.

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“…There are also a number of useful review articles published including guidelines how to use the traditional (and the new) assays for RONS detection, highlighting the specific pitfalls and drawbacks of them [28][29][30][31][32].…”

Section: Usefulness Of Traditional Rons Detection Assaysmentioning

confidence: 99%

“…using specific boronate probes [30]. Also fluorescein boronate probe was reported as a suitable assay for quantification of cell-derived peroxynitrite in endothelial cells and parasite-activated macrophages [141].…”

Section: No the Reaction Ofmentioning

confidence: 99%

Taking up the cudgels for the traditional reactive oxygen and nitrogen species detection assays and their use in the cardiovascular system

Daiber

Oelze

Sebastian

et al. 2017

Free Radical Biology and Medicine

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Keywords:Oxidative stress Redox signaling Fluorescence and chemiluminescence-based assays Dihydroethidium oxidative fluorescence microtopography Lucigenin-enhanced chemiluminescence L-012-enhanced chemiluminescence A B S T R A C T Reactive oxygen and nitrogen species (RONS such as H 2 O 2 , nitric oxide) confer redox regulation of essential cellular functions (e.g. differentiation, proliferation, migration, apoptosis), initiate and catalyze adaptive stress responses. In contrast, excessive formation of RONS caused by impaired break-down by cellular antioxidant systems and/or insufficient repair of the resulting oxidative damage of biomolecules may lead to appreciable impairment of cellular function and in the worst case to cell death, organ dysfunction and severe disease phenotypes of the entire organism. Therefore, the knowledge of the severity of oxidative stress and tissue specific localization is of great biological and clinical importance. However, at this level of investigation quantitative information may be enough. For the development of specific drugs, the cellular and subcellular localization of the sources of RONS or even the nature of the reactive species may be of great importance, and accordingly, more qualitative information is required. These two different philosophies currently compete with each other and their different needs (also reflected by different detection assays) often lead to controversial discussions within the redox research community. With the present review we want to shed some light on these different philosophies and needs (based on our personal views), but also to defend some of the traditional assays for the detection of RONS that work very well in our hands and to provide some guidelines how to use and interpret the results of these assays. We will also provide an overview on the "new assays" with a brief discussion on their strengths but also weaknesses and limitations.

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Toward selective detection of reactive oxygen and nitrogen species with the use of fluorogenic probes – Limitations, progress, and perspectives

Cited by 58 publications

References 71 publications

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

Mitochondria-Targeted Triphenylphosphonium-Based Compounds: Syntheses, Mechanisms of Action, and Therapeutic and Diagnostic Applications

N‐Heterocyclic Carbene Boranes as Reactive Oxygen Species‐Responsive Materials: Application to the Two‐Photon Imaging of Hypochlorous Acid in Living Cells and Tissues

Taking up the cudgels for the traditional reactive oxygen and nitrogen species detection assays and their use in the cardiovascular system

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