Cited by 1,418Redox biology and oxidative stressAntioxidant Activity and Oxidative StressFree Radicals and Antioxidants

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The Haber–Weiss reaction and mechanisms of toxicity

Kehrer, James P·2000·Toxicology

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Abstract

The concept that the highly reactive hydroxyl radical (HO) could be generated from an interaction between superoxide (O(2)(-)) and hydrogen peroxide (H(2)O(2)) was proposed (with Joseph Weiss) in Professor Haber's final paper published in 1934. Until it was recognized that free radicals are produced in biological systems, this finding seemed to have no relevance to biology. However, following the discovery that O(2)(-) was a normal cellular metabolite, it was quickly recognized that the Haber-Weiss reaction (O(2)(-)+H(2)O(2) -->HO+O(2)+HO(-)) might provide a means to generate more toxic radicals. Although the basic reaction has a second order rate constant of zero in aqueous solution and thus cannot occur in biological systems, the ability of iron salts to serve as catalysts was discussed by these authors. Because transition metal ions, particularly iron, are present at low levels in biological systems, this pathway (commonly referred to as the iron-catalyzed Haber-Weiss reaction) has been widely postulated to account for the in vivo generation of the highly reactive HO. Recent data documenting the importance of redox regulation of various cellular signaling pathways makes it clear that free radicals are essential for normal cellular function. However, this also makes it obvious that disruptions of free radical production or defenses at many different levels can lead to adverse effects on cells. While the generation of HO, which is by far the most reactive oxygen species, is generally indicative of an overtly toxic event, it is through studies at this level that we have reached a better understanding of free radicals as both signaling molecules and toxic species.

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“Fenton chemistry can also lead to the chemical decay of hydrogen peroxide and superoxide via the iron-catalyzed Haber-Weiss reaction (Equation 5), producing hydroxyl radicals in the presence of Fe(III) (Kehrer, 2000).”
Background
Biomimetic Cu, Zn and Cu2 complexes inserted in mesoporous silica as catalysts for superoxide dismutation
Patriarca, M., Daier, V., Camí, G., Pellegri, N., Rivière, É., Hureau, C., & Signorella, S. (2018) · Microporous and Mesoporous Materials · doi:10.1016/j.micromeso.2018.12.027 · Cited by 17
Usefulness of bile as a biomarker via ferroptosis and cysteine prenylation in cholangiocarcinoma; role of diagnosis and differentiation from benign biliary disease
Han, J., Ahn, K. S., Baek, W., Suh, S., Kim, Y., Kim, T., & Kang, K. J. (2020) · Surgical Oncology · doi:10.1016/j.suronc.2020.04.019 · Cited by 16
Influence of cytokines on Dmt1 iron transporter and ferritin expression in insulin-secreting cells
Lortz, S., Schröter, S., Stückemann, V., Mehmeti, I., & Lenzen, S. (2014) · Journal of Molecular Endocrinology · doi:10.1530/jme-13-0261 · Cited by 16
The promotive and repressive effects of exogenous H 2 O 2 on Arabidopsis seed germination and seedling establishment depend on application dose
Wang, Y., Liu, X., Sun, X., Mao, X., Wang, Z., Peng, J., Yang, Z., Ali, F., Wang, Z., & Li, F. (2025) · Physiologia Plantarum · doi:10.1111/ppl.70098 · Cited by 15
“If H 2 O 2 cannot be removed in time, it will be converted into more toxic (cid:129) OH by the Fenton reaction or Haber – Weiss reaction (Chen, 2019; Kehrer, 2000).”
Selected Natural Products in Neuroprotective Strategies for Alzheimer’s Disease—A Non-Systematic Review
Wojtunik‐Kulesza, K. A., Oniszczuk, T., Mołdoch, J., Kowalska, I., Szponar, J., & Oniszczuk, A. (2022) · International Journal of Molecular Sciences · doi:10.3390/ijms23031212 · Cited by 15
“Ocimum sanctum water extract,refluxed at 75–80 ◦C Wistar rats; male; maximal electroshock-, atropine-, and cyclosporine-induced dementia AChE cognitive behavioralperformance improvement [22] Ocimum sanctum Linn leaf extracted with 95% ethanol extract using Soxhlet Wistar rats; male; maximal electroshock-, atropine-, a…”
BackgroundInfluential
Mu opioid receptor-mediated release of endolysosome iron increases levels of mitochondrial iron, reactive oxygen species, and cell death
Halcrow, P. W., Kumar, N., Hao, E., Khan, N., Meucci, O., & Geiger, J. D. (2022) · NeuroImmune Pharmacology and Therapeutics · doi:10.1515/nipt-2022-0013 · Cited by 15
Cardioprotective Mechanisms against Reperfusion Injury in Acute Myocardial Infarction: Targeting Angiotensin II Receptors
Méndez-Valdés, G., Pérez-Carreño, V., Bragato, M. C., Hundahl, M. P., Chichiarelli, S., Saso, L., & Rodrigo, R. (2022) · Biomedicines · doi:10.3390/biomedicines11010017 · Cited by 18
“Free intracellular iron ions participate in the Fenton reaction and the Haber-Weiss reaction, the first being a chemical reaction between ferrous iron and H2O2, producing hydroxyl radical by oxidizing iron; in the latter, ferric iron is reduced again in the presence of superoxide radicals, also producing hydroxyl radi…”
Background
A chemical framework for the preservation of fossil vertebrate cells and soft tissues
Anderson, L. A. (2023) · Earth-Science Reviews · doi:10.1016/j.earscirev.2023.104367 · Cited by 16
“The free hydroxyl radical, being a highly reactive species, can quickly abstract a hydrogen atom from a biomolecule such as a protein, lipid (in the case of lipids this is equivalent to lipid peroxidation), etc., and form a radical on the biomolecule itself (Kehrer 2000; Roberfroid & Calderon 1995).”
Background
Ferroptosis: The functions of Nrf2 in human embryonic stem cells
Abraki, S. B., Karamali, F., & Nasr‐Esfahani, M. H. (2023) · Cellular Signalling · doi:10.1016/j.cellsig.2023.110654 · Cited by 16
In Vitro Antioxidant and In Vivo Antigenotoxic Features of a Series of 61 Essential Oils and Quantitative Composition–Activity Relationships Modeled through Machine Learning Algorithms
Mladenović, M. P., Astolfi, R., Tomašević, N., Matić, S. L., Božović, M., Sapienza, F. U., & Ragno, R. (2023) · Antioxidants · doi:10.3390/antiox12101815 · Cited by 16
“EOs can be considered preventive antioxidants as they can retard the initial formation of radical species within the Fenton-type [9] and Haber–Weiss reactions [10] by chelating the redox active metal ions (e.g., Fe 2+ ) [1].”
A Multipurpose Metallophore and Its Copper Complexes with Diverse Catalytic Antioxidant Properties to Deal with Metal and Oxidative Stress Disorders: A Combined Experimental, Theoretical, and In Vitro Study
Menezes, L. B., Sampaio, R. M. S. N., Meurer, L., Szpoganicz, B., Cervo, R., Cargnelutti, R., Wang, L., Yang, J., Prabhakar, R. S., Fernandes, C., et al. (2024) · Inorganic Chemistry · doi:10.1021/acs.inorgchem.4c00232 · Cited by 16
Iron Dyshomeostasis in Neurodegeneration with Brain Iron Accumulation (NBIA): Is It the Cause or the Effect?
Agostini, F., Sgalletta, B., & Bisaglia, M. (2024) · Cells · doi:10.3390/cells13161376 · Cited by 17
“The products of these chemical processes are the highly reactive hydroxyl radicals ( • HO) that may damage proteins, nucleic acids, and membrane lipids, ultimately leading to cell death [3,4].”
Background
PM 10‐stimulated airway epithelial cells activate primary human dendritic cells independent of uric acid: Application of an in vitro model system exposing dendritic cells to airway epithelial cell‐conditioned media
Hirota, J. A., Alexis, N. E., Pui, M. M., Wong, S., Fung, E., Hansbro, P. M., Knight, D. A., Sin, D. D., & Carlsten, C. (2014) · Respirology · doi:10.1111/resp.12316 · Cited by 15
Transcriptional and preliminary functional analysis of the six genes located in divergence of phoR/phoP in Streptomyces lividans
Darbon, E., Martel, C., Nowacka, A., Pégot, S., Moreau, P. L., & Virolle, M. (2012) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-012-3995-2 · Cited by 15
“The percentage of growth inhibition by tBHP and diamide was calculated on the basis of the following equation (1−[biomass average in the presence of oxidant/biomass average without oxidant])×100 and is indicated for each strain Haber–Weiss reactions (Fenton 1986; Kehrer 2000).”
Use of biochemical markers to quantify the toxicological effects of metals on the fish Sciades herzbergii: potential use to assess the environmental status of Amazon estuaries
Nunes, B., da Paixão, L. F., Nunes, Z. M. P., Amado, L. L., Ferreira, M. A. P., & da Rocha, R. M. (2020) · Environmental Science and Pollution Research · doi:10.1007/s11356-020-09362-3 · Cited by 14
“Fenton and Haber-Weiss reactions can also occur in the medium (Kehrer 2000).”
Background
Critical Role for Molecular Iron in Coxiella burnetii Replication and Viability
Sanchez, S. E., & Omsland, A. (2020) · mSphere · doi:10.1128/msphere.00458-20 · Cited by 15
Iron Overload Induced Apoptotic Cell Death in Isolated Rat Hepatocytes Mediated by Reactive Oxygen Species
Allameh, A., Amini-Harandi, A., & Osati-Ashtiani, F. (2008) · Iranian journal of pharmaceutical research · doi:10.22037/ijpr.2010.753 · Cited by 15
“O’Brien P / IJPR (2008), 7 (2): 115-121”
Background
Dual roles of reactive oxygen species in intertidal macroalgae Ulva prolifera under ultraviolet-B radiation
Zhao, X., Zheng, W. H., Qu, T., Zhong, Y., Xu, J., Jiang, Y., Zhang, H., Tang, X., & Wang, Y. (2021) · Environmental and Experimental Botany · doi:10.1016/j.envexpbot.2021.104534 · Cited by 15
Superoxide Processing
Miller, A. (2003) · Elsevier eBooks · doi:10.1016/b0-08-043748-6/08173-1 · Cited by 15
High oxygen as an additional factor in food preservation
Amanatidou, A. (2001) · doi:10.18174/121263 · Cited by 15
Electrochemical Processes During High‐Voltage Electric Pulses and their Importance in Food Processing Technology
Saulis, G., Rodaitė‐Riševičienė, R., Dainauskaitė, V. S., & Saulė, R. (2015) · Wiley eBooks · doi:10.1002/9781118864463.ch35 · Cited by 15
Assessment of Oxidative Stress and Associated Biomarkers in Wild Avian Species
Faraguna, S., Tur, S. M., Sobočanec, S., Pinterić, M., & Belić, M. (2025) · Animals · doi:10.3390/ani15091203 · Cited by 14
“Direct methods measure the amount of ROS, which is very difficult because free radicals have a very short half-life [35,154,155].”
Chapter 2: Function and regulation of porcine selenogenome and selenoproteome
Zhao, H. Y., Zhao, Z., & Lei, X. G. (2021) · Wageningen Academic Publishers eBooks · doi:10.3920/978-90-8686-912-1_2 · Cited by 14
Role of Fe, Transferrin and Transferrin Receptor in Anti-Tumor Effect of Vitamin C
Qiu, J., Wu, R., Long, Y., Peng, L., Yang, T., Zhang, B., Shi, X., Liu, J., & Zhang, X. (2022) · Cancers · doi:10.3390/cancers14184507 · Cited by 14
“Previous research confirmed that the formation of H2O2 depends on the oxidation of VC, which is related to metal ion redox chemistry [5,6].”
BackgroundInfluential
Pseudomonas aeruginosa Dps (PA0962) Functions in H2O2 Mediated Oxidative Stress Defense and Exhibits In Vitro DNA Cleaving Activity
Rajapaksha, N., Soldano, A., Yao, H., Donnarumma, F., Kashipathy, M. M., Seibold, S. A., Battaile, K. P., Lovell, S., & Rivera, M. (2023) · International Journal of Molecular Sciences · doi:10.3390/ijms24054669 · Cited by 13
“The requirement of iron as a nutrient, the reactivity of Fe2+ toward O2 and H2O2, and the insolubility of Fe3+ at biologically compatible pH present significant challenges to bacterial cells, which are managed by the iron homeostasis machinery (iron uptake, storage, and utilization) [1,2].”
Background
Development of an iron overload HepG2 cell model using ferrous ammonium citrate
Abbasi, U., Abbina, S., Gill, A., & Kizhakkedathu, J. (2023) · Scientific Reports · doi:10.1038/s41598-023-49072-7 · Cited by 13
“Elevated labile iron catalyzes the generation of ROS through the Haber–Weiss reaction, which imparts oxidative damage to lipids, proteins and DNA 22–24, 64 , 65 .”
BackgroundInfluential
Developing zinc oxide and peanut shell-derived carbon star-shaped composite materials for effective photo-antibacterial treatment
Ilhami, F. B., Fitriana, F., Mozef, T., Wihadi, M. N. K., Munasir, M., Khasanah, M., Putri, N. P., Kusumawati, D. H., Kao, C., Kuo, D., et al. (2024) · Heliyon · doi:10.1016/j.heliyon.2024.e32348 · Cited by 14
Echinoderm Reactive Oxygen Species (ROS) Production Measured by Peroxidase, Luminol-Enhanced Chemiluminescence (PLCL) as an Immunotoxicological Tool
Coteur, G., Danis, B., & Dubois, P. (2005) · Springer eBooks · doi:10.1007/3-540-27683-1_4 · Cited by 14
“Metals are known to take part in the formation of certain reactive species (Kehrer 2000) but can also act by inactivating divalent cation-requiring enzymes involved in ROS production.”
Background
QSPR/QSAR-based Perturbation Theory approach and mechanistic electrochemical assays on carbon nanotubes with optimal properties against mitochondrial Fenton reaction experimentally induced by Fe2+-overload
González‐Durruthy, M., de Castro, M. R., Nunes, S. M., Ventura‐Lima, J., Alberici, L. C., Naal, Z., Atique-Sawazaki, D. T., Curti, C., Ruas, C. P., Gelesky, M. A., et al. (2017) · Carbon · doi:10.1016/j.carbon.2017.01.002 · Cited by 14
Assessment of Techno-Functional and Nutraceutical Potential of Tomato (Solanum lycopersicum) Seed Meal
Maldonado-Torres, R., Morales-Camacho, J. I., López-Valdez, F., Huerta-González, L., & Luna‐Suárez, S. (2020) · Molecules · doi:10.3390/molecules25184235 · Cited by 14
“In this sense, metal chelating agents may inhibit reactive oxygen species production and prevent damage to DNA, protein, and lipids into cells [33].”
Background
Unlocking Survival Mechanisms for Metal and Oxidative Stress in the Extremely Acidophilic, Halotolerant Acidihalobacter Genus
Khaleque, H. N., Fathollahzadeh, H., González, C., Shafique, R., Kaksonen, A. H., Holmes, D. S., & Watkin, E. L. J. (2020) · Genes · doi:10.3390/genes11121392 · Cited by 14
“Examples of metal-coupled ROS generating reactions are the Fenton (Reaction (1)) and Haber–Weiss reactions (Reactions (2) and (1), resulting in net reaction 3) ([10,18,19].”
Background
Repression of the iron exporter ferroportin may contribute to hepatocyte iron overload in individuals with type 2 diabetes
Qiu, R., Alikhanyan, K., Volk, N., Marques, O., Mertens, C., Agarvas, A. R., Singh, S., Pepperkok, R., Altamura, S., & Muckenthaler, M. U. (2022) · Molecular Metabolism · doi:10.1016/j.molmet.2022.101644 · Cited by 16
“Free iron (Fe2þ) participates in the Fenton and HabereWeiss reactions to generate highly reactive superoxide anion (O2 ) and hydroxyl radicals (OH ) [23].”
Background
Potential Benefits of Lycopene Consumption: Rationale for Using It as an Adjuvant Treatment for Malaria Patients and in Several Diseases
Varela, E. L. P., Gomes, A. R. Q., dos Santos, A. D. S. B., de Carvalho, E., Vale, V. V., & Percário, S. (2022) · Nutrients · doi:10.3390/nu14245303 · Cited by 17
“the parasite manages to polymerize FPIX, resulting in a ntoxic derivative, hemozoin, als k own as malarial pigment, a s gnificant amount escapes polymerization [84].”
Comparative study on antioxidant activity of four varieties of F lammulina velutipes with different colour
Zhang, Z., Jin, Q., Lv, G., Fan, L., Pan, H., & Fan, L. (2013) · International Journal of Food Science & Technology · doi:10.1111/ijfs.12062 · Cited by 14
Severe oxidative stress in an acute inflammatory demyelinating model in the rhesus monkey
Dunham, J., van de Vis, R. A. J., Bauer, J., Wubben, J. A. M., van Driel, N., Laman, J. D., Hart, B. A. ‘., & Kap, Y. S. (2017) · PLoS ONE · doi:10.1371/journal.pone.0188013 · Cited by 14
The Main Targets Involved in Neuroprotection for the Treatment of Alzheimer’s Disease and Parkinson Disease
Gülcan, H. O., & Orhan, İ. E. (2020) · Current Pharmaceutical Design · doi:10.2174/1381612826666200131103524 · Cited by 14
Molecular Mechanisms of Cell Death
Lemasters, J. J. (2017) · Elsevier eBooks · doi:10.1016/b978-0-12-802761-5.00001-8 · Cited by 14
Moderate to severe liver siderosis and raised AST are independent risk factors for vitamin D insufficiency in β-thalassemia patients
Darvishi‐Khezri, H., Karami, H., Naderisorki, M., Zahedi, M., Razavi, A., Kosaryan, M., & Aliasgharian, A. (2020) · Scientific Reports · doi:10.1038/s41598-020-78230-4 · Cited by 14

Authors: Kehrer, J. P.
Affiliations: The University of Texas at Austin (US)
Corresponding author: Kehrer, James P
Venue: Toxicology
Publisher: Elsevier BV
Published: 2000-08
Volume: 149
Issue: 1
Pages: 43-50
ISSN: 0300-483X (ISSN-L)
DOI: 10.1016/s0300-483x(00)00231-6
OpenAlex: W2126473492
Cited by: 1,418
References: 39
Citations by year: 2026: 46 · 2025: 71 · 2024: 90 · 2023: 91 · 2022: 101 · 2021: 101 · 2020: 91 · 2019: 65 · 2018: 76 · 2017: 72 · 2016: 71 · 2015: 62 · 2014: 48 · 2013: 65 · 2012: 59
FWCI: 1.20
Type: journal article
Language: en
Open access: closed
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
Locations: Toxicology (publishedVersion)
PubMed (publishedVersion)
Funders: National Institutes of Health (5r01es009791-04, 5r01hl051005-05, 5r01hl048035-07)
National Heart, Lung, and Blood Institute (HL 48035, HL 51005)
National Institute of Environmental Health Sciences (ES09791)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
Health Sciences › Medicine › Biochemistry (medical) › Antioxidant Activity and Oxidative Stress
Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
Keywords: Haber-Weiss reaction, hydroxyl radicals, superoxide, hydrogen peroxide, free radicals, reactive oxygen species, oxidative stress, redox signaling, toxicity mechanisms, transition metal catalysis
MeSH terms: Animals, Humans, Hydrogen Peroxide, Superoxides, Hydroxyl Radical, Oxidative Stress

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The Haber–Weiss reaction and mechanisms of toxicity

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