Detection and differentiation between peroxynitrite and hydroperoxides using mitochondria-targeted arylboronic acid

Methods in Molecular Biology

Volumn 1264, Issue , 2015, Pages 171-181

  Zielonka, Jacek ^a,b   Sikora, Adam ^b   Adamus, Jan ^b   Kalyanaraman, B ^a  

^a FREE RADICAL RESEARCH CENTER   (United States)

^b LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Boronic probes; HPLC MS; Hydrogen peroxide; Mitochondria targeted probes; O MitoPhB(OH)2; Peroxynitrite

Indexed keywords

ARYLBORONIC ACID; BENZENEBORONIC ACID; HYDROPEROXIDE; OXIDIZING AGENT; PEROXYNITRITE; UNCLASSIFIED DRUG; BORONIC ACID DERIVATIVE; FLUORESCENT DYE; HYDROGEN PEROXIDE; PEROXYNITROUS ACID;

ANALYTIC METHOD; ARTICLE; CELL CULTURE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CLINICAL PROTOCOL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; LIMIT OF QUANTITATION; MITOCHONDRION; MOLECULAR BIOLOGY; OXIDATION; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; TANDEM MASS SPECTROMETRY; ANIMAL; CELL LINE; CHEMISTRY; METABOLISM; METABOLOMICS; MOUSE; PROCEDURES;

ANIMALS; BORONIC ACIDS; CELL LINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORESCENT DYES; HYDROGEN PEROXIDE; METABOLOMICS; MICE; MITOCHONDRIA; PEROXYNITROUS ACID; TANDEM MASS SPECTROMETRY;

EID: 84958629324     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-4939-2257-4_16     Document Type: Article

References (15)

1. Lippert AR, Van de Bittner GC, Chang CJ (2011) Boronate oxidation as a bioorthogonal reaction approach for studying the chemistry of hydrogen peroxide in living systems. Acc Chem Res 44:793–804
2. Zielonka J, Sikora A, Hardy M, Joseph J, Dranka BP, Kalyanaraman B (2012) Boronate probes as diagnostic tools for real time monitoring of peroxynitrite and hydroperoxides. Chem Res Toxicol 25:1793–1799
3. Cocheme HM, Quin C, McQuaker SJ, Cabreiro F, Logan A, Prime TA, Abakumova I, Patel JV, Fearnley IM, James AM, Porteous CM, Smith RA, Saeed S, Carre JE, Singer M, Gems D, Hartley RC, Partridge L, Murphy MP (2011) Measurement of H2O2 within living Drosophila during aging using a ratio-metric mass spectrometry probe targeted to the mitochondrial matrix. Cell Metab 13: 340–350
4. Cocheme HM, Logan A, Prime TA, Abakumova I, Quin C, McQuaker SJ, Patel JV, Fearnley IM, James AM, Porteous CM, Smith RA, Hartley RC, Partridge L, Murphy MP (2012) Using the mitochondria-targeted ratiometric mass spectrometry probe MitoB to measure H2O2 in living Drosophila. Nat Protoc 7:946–958
5. Dickinson BC, Chang CJ (2008) A targetable fluorescent probe for imaging hydrogen peroxide in the mitochondria of living cells. J Am Chem Soc 130:9638–9639
6. Dickinson BC, Lin VS, Chang CJ (2013) Preparation and use of MitoPY1 for imaging hydrogen peroxide in mitochondria of live cells. Nat Protoc 8:1249–1259
7. Sikora A, Zielonka J, Lopez M, Joseph J, Kalyanaraman B (2009) Direct oxidation of boronates by peroxynitrite: mechanism and implications in fluorescence imaging of peroxynitrite. Free Radic Biol Med 47: 1401–1407
8. Sikora A, Zielonka J, Lopez M, Dybala-Defratyka A, Joseph J, Marcinek A, Kalyanaraman B (2011) Reaction between peroxynitrite and boronates: EPR spin-trapping, HPLC analyses, and quantum mechanical study of the free radical pathway. Chem Res Toxicol 24:687–697
9. Kalyanaraman B (2011) Oxidative chemistry of fluorescent dyes: implications in the detection of reactive oxygen and nitrogen species. Biochem Soc Trans 39:1221–1225
10. Wardman P (2007) Fluorescent and luminescent probes for measurement of oxidative and nitrosative species in cells and tissues: progress, pitfalls, and prospects. Free Radic Biol Med 43:995–1022
11. Zielonka J, Kalyanaraman B (2012) Methods of investigation of selected radical oxygen/ nitrogen species in cell-free and cellular systems. In: Pantopoulos K, Schipper HM (eds) Principles of free radical biomedicine. Nova Science Publishers, New York, NY
12. Zielonka J, Sikora A, Joseph J, Kalyanaraman B (2010) Peroxynitrite is the major species formed from different flux ratios of co-generated nitric oxide and superoxide: direct reaction with boronate-based fluorescent probe. J Biol Chem 285:14210–14216
13. Zielonka J, Zielonka M, Sikora A, Adamus J, Joseph J, Hardy M, Ouari O, Dranka BP, Kalyanaraman B (2012) Global profiling of reactive oxygen and nitrogen species in biological systems: high-throughput real-time analyses. J Biol Chem 287:2984–2995
14. Sikora A, Zielonka J, Adamus J, Debski D, Dybala-Defratyka A, Michalowski B, Joseph J, Hartley RC, Murphy MP, Kalyanaraman B (2013) Reaction between peroxynitrite and triphenylphosphonium-substituted arylboronic acid isomers: identification of diagnostic marker products and biological implications. Chem Res Toxicol 26:856–867
15. Zielonka J, Joseph J, Sikora A, Kalyanaraman B (2013) Real-time monitoring of reactive oxygen and nitrogen species in a multiwell plate using the diagnostic marker products of specific probes. Methods Enzymol 526: 145–157