Cited by 144Neutrophil, Myeloperoxidase and Oxidative MechanismsRedox biology and oxidative stressWater Treatment and Disinfection

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Chlorination of Guanosine and Other Nucleosides by Hypochlorous Acid and Myeloperoxidase of Activated Human Neutrophils

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Masuda, Mitsuharu, Suzuki, Toshinori, Friesen, Marlin D., Ravanat, Jean-Luc, Cadet, Jean, Pignatelli, Brigitte, Nishino, Hoyoku, Ohshima, Hiroshi·2001·Journal of Biological Chemistry

DOI 10.1074/jbc.m102700200

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Abstract

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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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
ORCID: Suzuki, Toshinori
Ravanat, Jean-Luc
Cadet, Jean
Venue: Journal of Biological Chemistry
Publisher: Elsevier BV
Published: 2001-11
Volume: 276
Issue: 44
Pages: 40486-40496
ISSN: 0021-9258 (ISSN-L)
DOI: 10.1074/jbc.m102700200
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: cc-by
www.elsevier.com/tdm/userlicense/1.0/ (tdm)
creativecommons.org/licenses/by/4.0/ (vor, 6909 d)
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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Chlorination of Guanosine and Other Nucleosides by Hypochlorous Acid and Myeloperoxidase of Activated Human Neutrophils

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