ArticleFree radical biology & medicine2012
The reaction of HOCl and cyanocobalamin: corrin destruction and the liberation of cyanogen chloride.
Article in Free radical biology & medicine, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 45 citations in OpenAlex.
- Serum melatonin as a potential biomarker for COVID-19 severity.Scientific reports · 2025Article
- The chlorite adduct of aquacobalamin: contrast with chlorite dismutase.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2025Article
- Melatonin interferes with COVID-19 at several distinct ROS-related steps.Journal of inorganic biochemistry · 2021Review
- Mechanism of cyanocobalamin chlorination by hypochlorous acid.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2021Article
- Article
- Melatonin prevents hypochlorous acid-mediated cyanocobalamin destruction and cyanogen chloride generation.Journal of pineal research · 2018Article
- Reactions of aquacobalamin and cob(II)alamin with chlorite and chlorine dioxide.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2017Article
- Melatonin prevents myeloperoxidase heme destruction and the generation of free iron mediated by self-generated hypochlorous acid.PloS one · 2015Article
- Disruption of heme-peptide covalent cross-linking in mammalian peroxidases by hypochlorous acid.Journal of inorganic biochemistry · 2014Article
- Effect of ascorbic acid on the degradation of cyanocobalamin and hydroxocobalamin in aqueous solution: a kinetic study.AAPS PharmSciTech · 2014Article
- Article
- Myeloperoxidase acts as a source of free iron during steady-state catalysis by a feedback inhibitory pathway.Free radical biology & medicine · 2013Article
- Antioxidant effects of vitamins C and e on the low-density lipoprotein oxidation mediated by myeloperoxidase.Iranian biomedical journal · 2013Article
- Article
Corrections and comments
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Authors and funding
9 authors at 2 institutions in 1 country.
Funding
Abstract
Overproduction of hypochlorous acid (HOCl) has been associated with the development of a variety of disorders such as inflammation, heart disease, pulmonary fibrosis, and cancer through its ability to modify various biomolecules. HOCl is a potent oxidant generated by the myeloperoxidase-hydrogen peroxide-chloride system. Recently, we have provided evidence to support the important link between higher levels of HOCl and heme destruction and free iron release from hemoglobin and RBCs. Our current findings extend this work and show the ability of HOCl to mediate the destruction of metal-ion derivatives of tetrapyrrole macrocyclic rings, such as cyanocobalamin (Cobl), a common pharmacological form of vitamin B12. Cyanocobalamin is a water-soluble vitamin that plays an essential role as an enzyme cofactor and antioxidant, modulating nucleic acid metabolism and gene regulation. It is widely used as a therapeutic agent and supplement, because of its efficacy and stability. In this report, we demonstrate that although Cobl can be an excellent antioxidant, exposure to high levels of HOCl can overcome the beneficial effects of Cobl and generate proinflammatory reaction products. Our rapid kinetic, HPLC, and mass spectrometric analyses showed that HOCl can mediate corrin ring destruction and liberate cyanogen chloride (CNCl) through a mechanism that initially involves α-axial ligand replacement in Cobl to form a chlorinated derivative, hydrolysis, and cleavage of the phosphonucleotide moiety. Additionally, it can liberate free Co, which can perpetuate metal-ion-induced oxidant stress. Taken together, these results are the first report of the generation of toxic molecular products through the interaction of Cobl with HOCl.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.