Real-time Measurements of Amino Acid and Protein Hydroperoxides Using Coumarin Boronic Acid

Michalski, Radosław; Zielonka, Jacek; Gapys, Ewa; Marcinek, Andrzej; Joseph, Joy; Kalyanaraman, Balaraman

doi:10.1074/jbc.m114.553727

Cited by 65 publications

(68 citation statements)

References 54 publications

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“…Predominant addition of O 2 •− to G(-H) • gives rise through a complex sequence of reactions leading to 2,2,4-triamino-5(2 H )-oxazolone (Oz) [38] while relatively minor one-electron reduction leads to restoration of the guanine base in a chemical repair process. Similar O 2 •− addition reactions have also been observed for other highly oxidizing radicals that are derived from the one-electron oxidation of tyrosine and tryptophan, respectively [39,40]. …”

Section: Main Reactive Endogenous and Exogenous Cellular Oxidizing Spsupporting

confidence: 59%

Formation and repair of oxidatively generated damage in cellular DNA

Cadet

Davies

Medeiros

et al. 2017

Free Radical Biology and Medicine

272

228

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In this review article, emphasis is placed on the critical survey of available data concerning modified nucleobase and 2-deoxyribose products that have been identified in cellular DNA following exposure to a wide variety of oxidizing species and agents including, hydroxyl radical, one-electron oxidants, singlet oxygen, hypochlorous acid and ten-eleven translocation enzymes. In addition, information is provided about the generation of secondary oxidation products of 8-oxo-7,8-dihydroguanine and nucleobase addition products with reactive aldehydes arising from the decomposition of lipid peroxides. It is worth noting that the different classes of oxidatively generated DNA damage that consist of single lesions, intra- and interstrand cross-links were unambiguously assigned and quantitatively detected on the basis of accurate measurements involving in most cases high performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry. The reported data clearly show that the frequency of DNA lesions generated upon severe oxidizing conditions, including exposure to ionizing radiation is low, at best a few modifications per 106 normal bases. Application of accurate analytical measurement methods has also allowed the determination of repair kinetics of several well-defined lesions in cellular DNA that however concerns so far only a restricted number of cases.

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Section: Main Reactive Endogenous and Exogenous Cellular Oxidizing Spsupporting

confidence: 59%

Formation and repair of oxidatively generated damage in cellular DNA

Cadet

Davies

Medeiros

et al. 2017

Free Radical Biology and Medicine

272

228

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“…More recently, we have shown that selected amino acid hydroperoxides (AA-OOH) and protein hydroperoxides (Pr-OOH) also oxidize boronic compounds [16]. With all of the oxidants tested so far, the mechanism appears to be similar; a 1:1 stoichiometry between oxidant and boronate probes was observed, resulting in the same major product.…”

Section: Introductionmentioning

confidence: 99%

“…However, the main difference is the rate constant of the reaction between different oxidants and the boronate probe. The rate constants varied from 10 0 , 10 1 , 10 4 to 10 6 M −1 s −1 for H 2 O 2 , AA-OOH, HOCl and ONOO − , respectively [13,16]. Therefore, depending on the experimental settings, boronates may be used to detect different oxidants by monitoring the reaction products.…”

Section: Introductionmentioning

confidence: 99%

On the use of peroxy-caged luciferin (PCL-1) probe for bioluminescent detection of inflammatory oxidants in vitro and in vivo – Identification of reaction intermediates and oxidant-specific minor products

Zielonka

Podsiadly

Zielonka

et al. 2016

Free Radical Biology and Medicine

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Peroxy-caged luciferin (PCL-1) probe was first used to image hydrogen peroxide in living systems (Van de Bittner GC et al. Proc Natl Acad Sci U S A. 2010; 107:21316–21). Recently this probe was shown to react with peroxynitrite more potently than with hydrogen peroxide (Sieracki et al. Free Radic Biol Med. 2013; 61:40–50) and was suggested to be a more suitable probe for detecting peroxynitrite under in vivo conditions. In this work, we investigated in detail the products formed from the reaction between PCL-1 and hydrogen peroxide, hypochlorite, and peroxynitrite. HPLC analysis showed that hydrogen peroxide reacts slowly with PCL-1, forming luciferin as the only product. Hypochlorite reaction with PCL-1 yielded significantly less luciferin, as hypochlorite oxidized luciferin to form a chlorinated luciferin. Reaction between PCL-1 and peroxynitrite consists of a major and minor pathway. The major pathway results in luciferin and the minor pathway produces a radical-mediated nitrated luciferin. Radical intermediate was characterized by spin trapping. We conclude that monitoring of chlorinated and nitrated products in addition to bioluminescence in vivo will help identify the nature of oxidant responsible for bioluminescence derived from PCL-1.

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“…Recently, we have shown that CBA is oxidized to the highly fluorescent 7-hydroxycoumarin by amino acid and protein hydroperoxides [58]. Based on this observation, we have developed a fluorometric real-time assay to detect protein hydroperoxides (Fig.…”

Section: Introductionmentioning

confidence: 99%

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

Dębowska

Dębski

Hardy

et al. 2015

Pharmacological Reports

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Over the last forty years, there has been tremendous progress in understanding the biological reactions of reactive oxygen species (ROS) and reactive nitrogen species (RNS). It is widely accepted that the generation of ROS and RNS is involved in physiological and pathophysiological processes. To understand the role of ROS and RNS in a variety of pathologies, the specific detection of ROS and RNS is fundamental. Unfortunately, the intracellular detection and quantitation of ROS and RNS remains a challenge. In this short review, we have focused on the mechanistic and quantitative aspects of their detection with the use of selected fluorogenic probes. The challenges, limitations and perspectives of these methods are discussed.

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Real-time Measurements of Amino Acid and Protein Hydroperoxides Using Coumarin Boronic Acid

Cited by 65 publications

References 54 publications

Formation and repair of oxidatively generated damage in cellular DNA

Formation and repair of oxidatively generated damage in cellular DNA

On the use of peroxy-caged luciferin (PCL-1) probe for bioluminescent detection of inflammatory oxidants in vitro and in vivo – Identification of reaction intermediates and oxidant-specific minor products

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

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