The DOI matches its Crossref record; 49 of the 49 references it cites were found in a registry or an index.
Chlorination of Guanosine and Other Nucleosides by Hypochlorous Acid and Myeloperoxidase of Activated Human Neutrophils
Open accessAbstract
Activated human neutrophils secrete myeloperoxidase, which generates HOCl from H2O2 and Cl(-). We have found that various (2'-deoxy)nucleosides react with HOCl to form chlorinated (2'-deoxy)nucleosides, including novel 8-chloro(2'-deoxy)guanosine, 5-chloro(2'-deoxy)cytidine, and 8-chloro(2'-deoxy)adenosine formed in yields of 1.6, 1.6, and 0.2%, respectively, when 0.5 mM nucleoside reacted with 0.5 mM HOCl at pH 7.4. The relative chlorination, oxidation, and nitration activities of HOCl, myeloperoxidase, and activated human neutrophils in the presence and absence of nitrite were studied by analyzing 8-chloro-, 8-oxo-7,8-dihydro-, and 8-nitro-guanosine, respectively, using guanosine as a probe. 8-Chloroguanosine was always more easily formed than 8-oxo-7,8-dihydro- or 8-nitro-guanosine. Using electrospray ionization tandem mass spectrometry, we show that several chlorinated nucleosides including 8-chloro(2'-deoxy)guanosine are formed following exposure of isolated DNA or RNA to HOCl. Micromolar concentrations of tertiary amines such as nicotine and trimethylamine dramatically enhanced chlorination of free (2'-deoxy)nucleosides and nucleosides in RNA by HOCl. As the G-463A polymorphism of the MPO gene, which strongly reduces myeloperoxidase mRNA expression, is associated with a reduced risk of lung cancer, chlorination damage of DNA /RNA and nucleosides by myeloperoxidase and its enhancement by nicotine may be important in the pathophysiology of human diseases associated with tobacco habits.
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“Nucleic acids are important targets of chlorination stress with possible mutagenic, genotoxic, and cytotoxic outcomes downstream of chemical modification ( Figure 3C ) (39, 100–102).”
From Hypochlorous Acid: From Innate Immune Factor and Environmental Toxicant to Chemopreventive Agent Targeting Solar UV-Induced Skin Cancer (2022) · cites this paper as [100]
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Formation of Nitrating and Chlorinating Species by Reaction of Nitrite with Hypochlorous Acid
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Deborde, M., & von Gunten, U. (2007) · Water Research · doi:10.1016/j.watres.2007.07.025 · Cited by 2,124
DNA Base Damage by Reactive Oxygen Species, Oxidizing Agents, and UV Radiation
Cadet, J., & Wagner, J. R. (2013) · Cold Spring Harbor Perspectives in Biology · doi:10.1101/cshperspect.a012559 · Cited by 903
Self-citationReactive nitrogen species in the chemical biology of inflammation
Dedon, P. C., & Tannenbaum, S. R. (2004) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2003.12.017 · Cited by 681
Chemical basis of inflammation-induced carcinogenesis
Ohshima, H., Tatemichi, M., & Sawa, T. (2003) · Archives of Biochemistry and Biophysics · doi:10.1016/s0003-9861(03)00283-2 · Cited by 623
Self-citationHypochlorite-induced oxidation of amino acids, peptides and proteins
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Metadata
- Authors
- Masuda, M., Suzuki, T., Friesen, M. D., Ravanat, J.-L., Cadet, J., Pignatelli, B., Nishino, H., & Ohshima, H.
- Affiliations
- Kyoto Prefectural University of Medicine (JP)
- Centre international de recherche sur le cancer (FR)
- Commissariat à l'Énergie Atomique et aux Énergies Alternatives (FR)
- Corresponding author
- Ohshima, Hiroshi
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 2001-11
- Volume
- 276
- Issue
- 44
- Pages
- 40486-40496
- ISSN
- 0021-9258 (ISSN-L)
- OpenAlex
- W2074415956
- Cited by
- 144
- References
- 49
- Citations by year
- 2026: 1 · 2025: 3 · 2024: 5 · 2023: 1 · 2022: 4 · 2021: 5 · 2020: 6 · 2019: 3 · 2018: 4 · 2017: 5 · 2016: 9 · 2015: 5 · 2014: 6 · 2013: 6 · 2012: 9
- FWCI
- 3.02
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Journal of Biological Chemistry (publishedVersion, cc-by)
- PubMed (publishedVersion)
- HAL (submittedVersion, cc-by)
- Topics
- Life Sciences › Immunology and Microbiology › Immunology › Neutrophil, Myeloperoxidase and Oxidative Mechanisms
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Water Treatment and Disinfection
- Keywords
- hypochlorous acid, myeloperoxidase, activated neutrophils, 8-oxo-7,8-dihydroguanosine, tertiary amines, nicotine, trimethylamine, lung cancer risk, tobacco use, oxidative DNA damage
- MeSH terms
- Animals, Catalysis, Cattle, Chlorine, Guanosine, Humans, Hypochlorous Acid, Methylamines, Peroxidase, Neutrophils, Nucleosides, Neutrophil Activation, Spectrometry, Mass, Electrospray Ionization
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