Cited by 579Redox biology and oxidative stressNitric Oxide and Endothelin EffectsAntioxidant Activity and Oxidative Stress

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Detection and characterization of the product of hydroethidine and intracellular superoxide by HPLC and limitations of fluorescence

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Zhao, Hongtao, Joseph, Joy, Fales, Henry M., Sokoloski, Edward A., Levine, Rodney L., Vasquez-Vivar, Jeannette, Kalyanaraman, B.·2005·Proceedings of the National Academy of Sciences

DOI 10.1073/pnas.0501719102PMC PMC556312

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Here we report the structural characterization of the product formed from the reaction between hydroethidine (HE) and superoxide ( \documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \setlength{\oddsidemargin}{-69pt} \begin{document} \begin{equation*}{\mathrm{O}}_{2}^{{\bullet}-}\end{equation*}\end{document} ). By using mass spectral and NMR techniques, the chemical structure of this product was determined as 2-hydroxyethidium (2-OH-E + ). By using an authentic standard, we developed an HPLC approach to detect and quantitate the reaction product of HE and \documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \setlength{\oddsidemargin}{-69pt} \begin{document} \begin{equation*}{\mathrm{O}}_{2}^{{\bullet}-}\end{equation*}\end{document} formed in bovine aortic endothelial cells after treatment with menadione or antimycin A to induce intracellular reactive oxygen species. Concomitantly, we used a spin trap, 5- tert -butoxycarbonyl-5-methyl-1-pyrroline N -oxide (BMPO), to detect and identify the structure of reactive oxygen species formed. BMPO trapped the \documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \setlength{\oddsidemargin}{-69pt} \begin{document} \begin{equation*}{\mathrm{O}}_{2}^{{\bullet}-}\end{equation*}\end{document} that formed extracellularly and was detected as the BMPO-OH adduct during use of the EPR technique. BMPO, being cell-permeable, inhibited the intracellular formation of 2-OH-E + . However, the intracellular BMPO spin adduct was not detected. The definitive characterization of the reaction product of \documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \setlength{\oddsidemargin}{-69pt} \begin{document} \begin{equation*}{\mathrm{O}}_{2}^{{\bullet}-}\end{equation*}\end{document} with HE described here forms the basis of an unambiguous assay for intracellular detection and quantitation of \documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \setlength{\oddsidemargin}{-69pt} \begin{document} \begin{equation*}{\mathrm{O}}_{2}^{{\bullet}-}\end{equation*}\end{document} . Analysis of the fluorescence characteristics of ethidium (E + ) and 2-OH-E + strongly suggests that the currently available fluorescence methodology is not suitable for quantitating intracellular \documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \setlength{\oddsidemargin}{-69pt} \begin{document} \begin{equation*}{\mathrm{O}}_{2}^{{\bullet}-}\end{equation*}\end{document} . We conclude that the HPLC/fluorescence assay using HE as a probe is more suitable reactive oxygen species for detecting intracellular \documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \setlength{\oddsidemargin}{-69pt} \begin{document} \begin{equation*}{\mathrm{O}}_{2}^{{\bullet}-}\end{equation*}\end{document} .

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Authors: Zhao, H., Joseph, J., Fales, H. M., Sokoloski, E. A., Levine, R. L., Vasquez-Vivar, J., & Kalyanaraman, B.
Affiliations: Medical College of Wisconsin (US)
University of Wisconsin–Madison (US)
ORCID: Zhao, Hongtao
Levine, Rodney L.
Vasquez-Vivar, Jeannette
Venue: Proceedings of the National Academy of Sciences
Publisher: National Academy of Sciences
Published: 2005-04-11
Volume: 102
Issue: 16
Pages: 5727-5732
ISSN: 0027-8424 (ISSN-L)
1091-6490
DOI: 10.1073/pnas.0501719102
PMC: PMC556312
OpenAlex: W1989224728
Cited by: 576
References: 26
Citations by year: 2026: 10 · 2025: 11 · 2024: 20 · 2023: 21 · 2022: 19 · 2021: 28 · 2020: 19 · 2019: 22 · 2018: 24 · 2017: 29 · 2016: 32 · 2015: 28 · 2014: 31 · 2013: 40 · 2012: 35
FWCI: 13.05
Type: journal article
Language: en
Update notices: correction (2005-06-21)
Open access: green
www.ncbi.nlm.nih.gov
Locations: Proceedings of the National Academy of Sciences (publishedVersion)
Europe PMC (PubMed Central) (publishedVersion)
PubMed Central (publishedVersion)
PubMed (publishedVersion)
Funders: National Institutes of Health (5P01HL68769-01)
National Heart, Lung, and Blood Institute (5P01HL68769-01, P01HL068769, R01HL067244)
National Cancer Institute (5R01 CA 77822, R01CA077822)
National Institute of Diabetes and Digestive and Kidney Diseases
National Institute of Neurological Disorders and Stroke (R01NS039958, 2R01NS39958)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
Health Sciences › Medicine › Physiology (medical) › Nitric Oxide and Endothelin Effects
Health Sciences › Medicine › Biochemistry (medical) › Antioxidant Activity and Oxidative Stress
Keywords: hydroethidine, superoxide, reactive oxygen species, spin trapping, menadione, antimycin A, endothelial cells, HPLC determination, electron spin resonance, superoxide detection, membrane permeability, intracellular reactive oxygen species, extracellular superoxide, spin adducts
MeSH terms: Animals, Aorta, Biological Assay, Cattle, Ceramides, Chromatography, High Pressure Liquid, Cyclic N-Oxides, Fluorescent Dyes, Oxidation-Reduction, Phenanthridines, Superoxides, Molecular Structure, Reactive Oxygen Species, Spin Trapping, Vitamin K 3, Endothelial Cells

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Detection and characterization of the product of hydroethidine and intracellular superoxide by HPLC and limitations of fluorescence

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