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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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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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“but most experimental studies show that even a slight decrease in ΔΨm (191, 201, 324) or transmatrix ΔpH (201) results in marked reduction or cessation of ROS production.”
From Mitochondrial reactive oxygen species production in excitable cells: Modulators of mitochondrial and cell function (2009) · cites this paper as [324]
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Metadata
- 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)
- 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
- 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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