Ergothioneine Prevents Copper-Induced Oxidative Damage to DNA and Protein by Forming a Redox-Inactive Ergothioneine−Copper Complex

Zhu, Ben-Zhan; Mao, Li; Fan, Rui-Mei; Zhu, Jun-Ge; Zhang, Ying-Nan; Wang, Jing; Kalyanaraman, Balaraman; Frei, Balz

doi:10.1021/tx100214t

Cited by 122Sulfur Compounds in BiologyFree Radicals and AntioxidantsAntioxidant Activity and Oxidative Stress

Ergothioneine Prevents Copper-Induced Oxidative Damage to DNA and Protein by Forming a Redox-Inactive Ergothioneine−Copper Complex

Zhu, Ben-Zhan, Mao, Li, Fan, Rui-Mei, Zhu, Jun-Ge, Zhang, Ying-Nan, Wang, Jing, Kalyanaraman, Balaraman, Frei, Balz·2011·Chemical Research in Toxicology

DOI 10.1021/tx100214t

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Abstract

Ergothioneine (2-mercaptohistidine trimethylbetaine) is a naturally occurring amino acid analogue found in up to millimolar concentrations in several tissues and biological fluids. However, the biological functions of ergothioneine remain incompletely understood. In this study, we investigated the role of ergothioneine in copper-induced oxidative damage to DNA and protein, using two copper-containing systems: Cu(II) with ascorbate and Cu(II) with H(2)O(2) [0.1 mM Cu(II), 1 mM ascorbate, and 1 mM H(2)O(2)]. Oxidative damage to DNA and bovine serum albumin was measured as strand breakage and protein carbonyl formation, respectively. Ergothioneine (0.1-1.0 mM) provided strong, dose-dependent protection against oxidation of DNA and protein in both copper-containing systems. In contrast, only limited protection was observed with the purported hydroxyl radical scavengers, dimethyl sulfoxide and mannitol, even at concentrations as high as 100 mM. Ergothioneine also significantly inhibited copper-catalyzed oxidation of ascorbate and competed effectively with histidine and 1,10-phenanthroline for binding of cuprous copper, but not cupric copper, as demonstrated by UV-visible and low-temperature electron spin resonance techniques. We conclude that ergothioneine is a potent, natural sulfur-containing antioxidant that prevents copper-dependent oxidative damage to biological macromolecules by forming a redox-inactive ergothioneine-copper complex.

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ERG has been shown to protect against a range of oxidative and toxic insults, including decreasing oxidative stress in rat liver and kidney, rescuing cells from β-amyloid-induced apoptotic death, protecting against palmitic acid-induced cell death, mercuric chloride-induced cellular dysfunction, and Cu-induced oxidative DNA damage.
“ERG has been shown to decrease oxidative stress in the liver and kidney of rats(469), rescued cells from β-amyloid-induced apoptotic death(231), protected against palmitic acid-induced cell death(470), mercuric chloride-induced cellular dysfunction(471), and prevented Cu-induced oxidative damage to DNA(472,473).”
From The biology of ergothioneine, an antioxidant nutraceutical (2020) · cites this paper as [473]

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Authors: Zhu, B.-Z., Mao, L., Fan, R.-M., Zhu, J.-G., Zhang, Y.-N., Wang, J., Kalyanaraman, B., & Frei, B.
Affiliations: Oregon State University (US)
State Key Laboratory of Environmental Chemistry and Eco-Toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, P. R. China, Linus Pauling Institute, Oregon State University, Corvallis, Oregon 97331, United States, and Biophysics Research Institute, Medical College of Wisconsin, Milwaukee, Wisconsin 53226-3548, United States
Corresponding author: Zhu, Ben-Zhan
Frei, Balz
ORCID: Zhu, Ben-Zhan
Mao, Li
Wang, Jing
Kalyanaraman, Balaraman
Venue: Chemical Research in Toxicology
Publisher: American Chemical Society (ACS)
Published: 2010-11-03
Volume: 24
Issue: 1
Pages: 30-34
ISSN: 0893-228X (ISSN-L)
1520-5010
DOI: 10.1021/tx100214t
OpenAlex: W1973294011
Cited by: 122
References: 34
Citations by year: 2026: 17 · 2025: 10 · 2024: 7 · 2023: 11 · 2022: 7 · 2021: 10 · 2020: 9 · 2019: 8 · 2018: 2 · 2017: 4 · 2016: 8 · 2015: 4 · 2014: 10 · 2013: 7 · 2012: 3
FWCI: 2.17
Type: journal article
Language: en
Open access: closed
Locations: Chemical Research in Toxicology (publishedVersion)
PubMed (publishedVersion)
Funders: National Institutes of Health (1r03es011497-01)
National Institute of Environmental Health Sciences (ES-00-210, ES11497, P30ES000210)
National Center for Research Resources (P41RR001008, RR 01008)
National Center for Complementary and Integrative Health (P01AT002034, AT 002034)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Sulfur Compounds in Biology
Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
Health Sciences › Medicine › Biochemistry › Antioxidant Activity and Oxidative Stress
Keywords: ergothioneine, copper, oxidative DNA damage, protein oxidation, antioxidants, ascorbic acid oxidation, hydrogen peroxide, hydroxyl radical scavengers, protein carbonylation, DNA strand breaks
MeSH terms: Animals, Ascorbic Acid, Cattle, Copper, Dimethyl Sulfoxide, DNA, DNA Damage, Electron Spin Resonance Spectroscopy, Ergothioneine, Histidine, Hydrogen Peroxide, Mannitol, Oxidation-Reduction, Phenanthrolines, Serum Albumin, Bovine, Free Radical Scavengers, Protein Carbonylation, Coordination Complexes

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Ergothioneine Prevents Copper-Induced Oxidative Damage to DNA and Protein by Forming a Redox-Inactive Ergothioneine−Copper Complex

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