Hypochlorite-Induced Damage to DNA, RNA, and Polynucleotides: Formation of Chloramines and Nitrogen-Centered Radicals
Abstract
Stimulated monocytes and neutrophils generate hypochlorite (HOCl) via the release of the enzyme myeloperoxidase and hydrogen peroxide. HOCl is a key bactericidal agent, but can also damage host tissue. As there is a strong link between chronic inflammation and some cancers, we have investigated HOCl damage to DNA, RNA, and polynucleotides. Reaction of HOCl with these materials is shown to yield multiple semistable chloramines (RNHCl/RR'NCl), which are the major initial products, and account for 50-95% of the added HOCl. These chloramines decay by thermal and metal-ion catalyzed processes, to give nucleoside-derived, nitrogen-centered, radicals. The latter have been characterized by EPR spin trapping. The propensity for radical formation with polynucleotides is cytidine > adenosine = guanosine > uridine = thymidine. The rates of decay, and yield of radicals formed, are dependent on the nature of the nucleobase on which they are formed, with chloramines formed from ring heterocyclic amine groups being less stable than those formed on exocyclic amines (RNH2 groups). Evidence is presented for chlorine transfer from the former, kinetically favored, sites to the more thermodynamically favored exocyclic amines. EPR experiments have also provided evidence for the rapid addition of pyrimidine-derived nitrogen-centered radicals to other nucleobases to give dimers and the oxidation of DNA by radicals derived from preformed nucleoside chloramines. Direct reaction of HOCl with plasmid DNA gives rise to single- and double-strand breaks via chloramine-mediated reactions. Preformed nucleoside chloramines also induce plasmid cleavage, though this only occurs to a significant extent with unstable thymidine- and uridine-derived chloramines, where radical formation is rapid. Overall the data rationalize the preferential formation of chlorinated 2'-deoxycytidine and 2'-deoxyadenosine in DNA and suggest that DNA damage induced by HOCl, and preformed chloramines, occurs at sequence-specific sites.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Nucleic acids are important targets of chlorination stress with possible mutagenic, genotoxic, and cytotoxic outcomes downstream of chemical modification.
“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 [101]
Cites
The Chemical Basis of Radiation Biology
O'Neill, P. (1987) · International Journal of Radiation Biology and Related Studies in Physics Chemistry and Medicine · doi:10.1080/09553008714552571 · Cited by 1,844 · see citing works
Simulation of Multiple Isotropic Spin-Trap EPR Spectra
Duling, D. (1994) · Journal of Magnetic Resonance Series B · doi:10.1006/jmrb.1994.1062 · Cited by 940 · see citing works
The Acid Ionization Constant of HOCl from 5 to 35°
Morris, J. C. (1966) · The Journal of Physical Chemistry · doi:10.1021/j100884a007 · Cited by 927 · see citing works
Hawkins, C. L., & Davies, M. J. (1998) · Biochemical Journal · doi:10.1042/bj3320617 · Cited by 305 · see citing works
Self-citationHawkins, C. L., & Davies, M. J. (1999) · Biochemical Journal · doi:10.1042/bj3400539 · Cited by 201 · see citing works
Self-citationNimmo, G. A., McNaughton, G. A. L., Fewson, C. A., Wilkins, M. B., & Nimmo, H. G. (1987) · FEBS Letters · doi:10.1016/0014-5793(87)81457-6 · Cited by 107 · see citing works
Molecular basis of oxidative damage by leukocytes
Dratz, E. A., & Jesaitis, A. J. (1993) · Free Radical Biology and Medicine · doi:10.1016/0891-5849(93)90132-e · Cited by 92 · see citing works
Arnhold, J., Panasenko, O. M., Schiller, J., IuA, V., & Arnold, K. (1995) · Chemistry and Physics of Lipids · doi:10.1016/0009-3084(95)02484-z · Cited by 75 · see citing works
Nucleotide chloramines and neutrophil‐mediated cytotoxicity
Bernofsky, C. (1991) · The FASEB Journal · doi:10.1096/fasebj.5.3.1848195 · Cited by 65 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
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 · see citing works
Hypochlorite-induced oxidation of amino acids, peptides and proteins
Hawkins, C. L., Pattison, D. I., & Davies, M. J. (2003) · Amino Acids · doi:10.1007/s00726-003-0016-x · Cited by 600 · see citing works
Self-citationMammalian Heme Peroxidases: From Molecular Mechanisms to Health Implications
Davies, M. J., Hawkins, C. L., Pattison, D. I., & Rees, M. D. (2008) · Antioxidants and Redox Signaling · doi:10.1089/ars.2007.1927 · Cited by 556 · see citing works
Self-citationFormation and repair of oxidatively generated damage in cellular DNA
Cadet, J., Davies, K. J. A., de Medeiros, M. H. G., Mascio, P. D., & Wagner, J. R. (2017) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2016.12.049 · Cited by 356 · see citing works
Photostable Ratiometric Pdot Probe for in Vitro and in Vivo Imaging of Hypochlorous Acid
Wu, L. J., Wu, I., DuFort, C. C., Carlson, M. A., Wu, X., Chen, L., Kuo, C.-T., Qin, Y., Yu, J., Hingorani, S. R., et al. (2017) · Journal of the American Chemical Society · doi:10.1021/jacs.7b01545 · Cited by 350 · see citing works
The Role of Myeloperoxidase in Biomolecule Modification, Chronic Inflammation, and Disease
Davies, M. J., & Hawkins, C. L. (2020) · Antioxidants & Redox Signaling · doi:10.1089/ars.2020.8030 · Cited by 332 · see citing works
Self-citationChlorine disinfection facilitates natural transformation through ROS-mediated oxidative stress
Zhang, S., Wang, Y., Lu, J., Yu, Z., Song, H., Bond, P. L., & Guo, J. (2021) · The ISME Journal · doi:10.1038/s41396-021-00980-4 · Cited by 324 · see citing works
Duan, C., Won, M., Verwilst, P., Xu, J., Kim, H. S., Zeng, L., & Kim, J. S. (2019) · Analytical Chemistry · doi:10.1021/acs.analchem.9b00224 · Cited by 322 · see citing works
Bacterial Responses to Reactive Chlorine Species
Gray, M. J., Wholey, W.-Y., & Jakob, U. (2013) · Annual Review of Microbiology · doi:10.1146/annurev-micro-102912-142520 · Cited by 303 · see citing works
Redox signaling and cancer: The role of “labile” iron
Galaris, D., Skiada, V., & Barbouti, A. (2008) · Cancer Letters · doi:10.1016/j.canlet.2008.02.038 · Cited by 284 · see citing works
Bull, R. J., Reckhow, D. A., Li, X., Humpage, A. R., Joll, C. A., & Hrudey, S. E. (2011) · Toxicology · doi:10.1016/j.tox.2011.05.004 · Cited by 255 · see citing works
The Roles of Neutrophil-Derived Myeloperoxidase (MPO) in Diseases: The New Progress
Lin, W. C., Chen, H., Chen, X., & Guo, C. (2024) · Antioxidants · doi:10.3390/antiox13010132 · Cited by 274 · see citing works
Block, M. S., & Rowan, B. G. (2020) · Journal of Oral and Maxillofacial Surgery · doi:10.1016/j.joms.2020.06.029 · Cited by 252 · see citing works
He, H., Zhou, P., Shimabuku, K. K., Fang, X., Li, S., Lee, Y., & Dodd, M. C. (2019) · Environmental Science & Technology · doi:10.1021/acs.est.8b04393 · Cited by 227 · see citing works
Surviving Reactive Chlorine Stress: Responses of Gram-Negative Bacteria to Hypochlorous Acid
Nizer, W. S. D. C., Inkovskiy, V., & Overhage, J. (2020) · Microorganisms · doi:10.3390/microorganisms8081220 · Cited by 196 · see citing works
Malle, E., Marsche, G., Arnhold, J., & Davies, M. J. (2006) · Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids · doi:10.1016/j.bbalip.2006.03.024 · Cited by 184 · see citing works
Self-citationHawkins, C. L., & Davies, M. J. (2021) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2021.07.007 · Cited by 181 · see citing works
Self-citationOxidative Stress Response in Pseudomonas aeruginosa
Nizer, W. S. D. C., Inkovskiy, V., Versey, Z., Strempel, N., Cassol, E., & Overhage, J. (2021) · Pathogens · doi:10.3390/pathogens10091187 · Cited by 169 · see citing works
Hypochlorous acid as a precursor of free radicals in living systems
Panasenko, O. M., Gorudko, I. V., & Av, S. (2013) · Biochemistry (Moscow) · doi:10.1134/s0006297913130075 · Cited by 157 · see citing works
Tan, H., Wu, X., Weng, Y., Lu, Y., & Huang, Z. (2020) · Analytical Chemistry · doi:10.1021/acs.analchem.9b05565 · Cited by 154 · see citing works
Bulky DNA Lesions Induced by Reactive Oxygen Species
Wang, Y. (2008) · Chemical Research in Toxicology · doi:10.1021/tx700411g · Cited by 152 · see citing works
Siraki, A. G. (2021) · Redox Biology · doi:10.1016/j.redox.2021.102109 · Cited by 150 · see citing works
Halogen Bonding in DNA Base Pairs
Parker, A. J., Stewart, J., Donald, K. J., & Parish, C. A. (2012) · Journal of the American Chemical Society · doi:10.1021/ja2105027 · Cited by 133 · see citing works
Organic chloramines in chlorine-based disinfected water systems: A critical review
How, Z. T., Kristiana, I., Busetti, F., Linge, K. L., & Joll, C. A. (2017) · Journal of Environmental Sciences · doi:10.1016/j.jes.2017.05.025 · Cited by 135 · see citing works
Davies, M. J. (2021) · Pharmacology & Therapeutics · doi:10.1016/j.pharmthera.2020.107685 · Cited by 119 · see citing works
Self-citationComparative reactivity of myeloperoxidase-derived oxidants with mammalian cells
Rayner, B. S., Love, D. T., & Hawkins, C. L. (2014) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2014.03.004 · Cited by 114 · see citing works
Self-citationRole of Reactive Oxygen Intermediates in Cellular Responses to Dietary Cancer Chemopreventive Agents
Antosiewicz, J., Ziółkowski, W., Kar, S., Powolny, A. A., & Singh, S. V. (2008) · Planta Medica · doi:10.1055/s-2008-1081307 · Cited by 105 · see citing works
REES, M. D., HAWKINS, C. L., & DAVIES, M. J. (2004) · Biochemical Journal · doi:10.1042/bj20040148 · Cited by 100 · see citing works
Self-citationMyeloperoxidase-induced Genomic DNA-centered Radicals
Gomez-Mejiba, S., Zhai, Z., Giménez, M. S., Ashby, M. T., Chilakapati, J., Kitchin, K. T., Mason, R. P., & Ramírez, D. C. (2010) · Journal of Biological Chemistry · doi:10.1074/jbc.m109.086579 · Cited by 85 · see citing works
Kawai, Y., Kiyokawa, H., Kimura, Y., Kato, Y., Tsuchiya, K., & Terao, J. (2006) · Biochemistry · doi:10.1021/bi0610909 · Cited by 78 · see citing works
Gorudko, I. V., Grigorieva, D. V., Shamova, E. V., Kostevich, V. A., Av, S., Mikhalchik, E. V., Cherenkevich, S. N., Arnhold, J., & Panasenko, O. M. (2014) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2013.12.023 · Cited by 77 · see citing works
Badouard, C., Masuda, M., Nishino, H., Cadet, J., Favier, A. E., & Ravanat, J. (2005) · Journal of Chromatography B · doi:10.1016/j.jchromb.2005.03.025 · Cited by 73 · see citing works
Ceruloplasmin and myeloperoxidase in complex affect the enzymatic properties of each other
Av, S., Ageeva, K. V., Pulina, M. O., Cherkalina, O. S., Самыгина, В. Р., Vlasova, I. I., Panasenko, O. M., Zakharova, E. T., & Vasilyev, V. B. (2008) · Free Radical Research · doi:10.1080/10715760802566574 · Cited by 71 · see citing works
Hawkins, C. L., Pattison, D. I., & Davies, M. J. (2002) · Biochemical Journal · doi:10.1042/bj20020363 · Cited by 69 · see citing works
Self-citationCold atmospheric-pressure plasma induces DNA–protein crosslinks through protein oxidation
Guo, L., Zhao, Y., Liu, D., Liu, Z., Chen, C., Xu, R., Tian, M., Wang, X., Chen, H., & Kong, M. G. (2018) · Free Radical Research · doi:10.1080/10715762.2018.1471476 · Cited by 67 · see citing works
Wu, P., & Xiong, H. (2022) · Talanta · doi:10.1016/j.talanta.2022.123584 · Cited by 67 · see citing works
Immuno–spin trapping of DNA radicals
Ramírez, D. C., Gomez-Mejiba, S., & Mason, R. P. (2006) · Nature Methods · doi:10.1038/nmeth852 · Cited by 61 · see citing works
Bonini, M. G., Siraki, A. G., Atanassov, B. S., & Mason, R. P. (2006) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2006.11.019 · Cited by 60 · see citing works
Endogenous Formation of Novel Halogenated 2′-Deoxycytidine
Kawai, Y., Morinaga, H., KONDO, H., Miyoshi, N., Nakamura, Y., Uchida, K., & Osawa, T. (2004) · Journal of Biological Chemistry · doi:10.1074/jbc.m408210200 · Cited by 60 · see citing works
DNA of Dientamoeba fragilis detected within surface-sterilized eggs of Enterobius vermicularis
Röser, D., Nejsum, P. L., Carlsgart, J., Nielsen, H. V., & Stensvold, C. R. (2012) · Experimental Parasitology · doi:10.1016/j.exppara.2012.10.009 · Cited by 59 · see citing works
Kim, K. H., Kim, S. J., Singha, S., Yang, Y. J., Park, S. K., & Ahn, K. H. (2021) · ACS Sensors · doi:10.1021/acssensors.1c00930 · Cited by 58 · see citing works
Zhang, M., Chen, S. Q., Yu, X., Vikesland, P. J., & Pruden, A. J. (2019) · Frontiers of Environmental Science & Engineering · doi:10.1007/s11783-019-1124-5 · Cited by 57 · see citing works
Disinfectants against SARS-CoV-2: A Review
Xiao, S., Yuan, Z., & Huang, Y. P. (2022) · Viruses · doi:10.3390/v14081721 · Cited by 54 · see citing works
A benzothiazole-based fluorescent probe for hypochlorous acid detection and imaging in living cells
Nguyen, K. H., Hao, Y., Zeng, K., Fan, S., Li, F., Yuan, S., Ding, X., Xu, M., & Liu, Y. (2018) · Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy · doi:10.1016/j.saa.2018.03.055 · Cited by 52 · see citing works
Dickerhof, N., Isles, V., Pattemore, P., Hampton, M. B., & Kettle, A. J. (2019) · Journal of Biological Chemistry · doi:10.1074/jbc.ra119.009934 · Cited by 49 · see citing works
Yoon, Y., He, H., Dodd, M. C., & Lee, Y. (2021) · Water Research · doi:10.1016/j.watres.2021.117408 · Cited by 51 · see citing works
Frégeau, C. J., Lett, C. M., Elliott, J., Yensen, C., & Fourney, R. M. (2008) · Journal of Forensic Sciences · doi:10.1111/j.1556-4029.2008.00697.x · Cited by 49 · see citing works
Galloylated Catechins as Potent Inhibitors of Hypochlorous Acid-induced DNA Damage
Kawai, Y., Matsui, Y., KONDO, H., Morinaga, H., Uchida, K., Miyoshi, N., Nakamura, Y., & Osawa, T. (2008) · Chemical Research in Toxicology · doi:10.1021/tx800069e · Cited by 47 · see citing works
Chaviara, A. T., Kioseoglou, E., Pantazaki, Α. A., Tsipis, A. C., Karipidis, P. A., Kyriakidis, D. A., & Bolos, C. A. (2008) · Journal of Inorganic Biochemistry · doi:10.1016/j.jinorgbio.2008.05.005 · Cited by 47 · see citing works
Hypochlorous Acid Damages Histone Proteins Forming 3-Chlorotyrosine and 3,5-Dichlorotyrosine
Kang, J. I., & Neidigh, J. W. (2008) · Chemical Research in Toxicology · doi:10.1021/tx7003486 · Cited by 47 · see citing works
El‐Fakharany, E. M., Uversky, V. N., & Redwan, E. M. M. M. (2016) · Applied Biochemistry and Biotechnology · doi:10.1007/s12010-016-2327-x · Cited by 47 · see citing works
Camps, J., Pommel, L., Aubut, V., Verhille, B., Fukuzaki, S., Lascola, B., & About, I. (2009) · Oral Surgery Oral Medicine Oral Pathology Oral Radiology and Endodontology · doi:10.1016/j.tripleo.2009.03.034 · Cited by 47 · see citing works
Aminyl and iminyl radicals from arylhydrazones in the photo-induced DNA cleavage
Hwu, J. R., Lin, C. C., Chuang, S. H., King, K. Y., Su, T., & Tsay, S. (2004) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2004.03.037 · Cited by 43 · see citing works
Chemical, cytotoxic and genotoxic analysis of etidronate in sodium hypochlorite solution
Ballal, N. V., Das, S., Rao, B. S. S., Zehnder, M., & Mohn, D. (2019) · International Endodontic Journal · doi:10.1111/iej.13110 · Cited by 43 · see citing works
Kang, P., Dalvie, D., Smith, E., Zhou, S., & Deese, A. J. (2007) · Drug Metabolism and Disposition · doi:10.1124/dmd.107.014860 · Cited by 42 · see citing works
Hu, Z., & Bai, X. (2023) · Water Research · doi:10.1016/j.watres.2023.120585 · Cited by 40 · see citing works
Jiang, P., Huang, G., Blackstock, L. K. J., Zhang, J., & Li, X. (2017) · Analytical Chemistry · doi:10.1021/acs.analchem.7b04262 · Cited by 40 · see citing works
Non-Canonical Functions of Myeloperoxidase in Immune Regulation, Tissue Inflammation and Cancer
Lockhart, J., & Sumagin, R. (2022) · International Journal of Molecular Sciences · doi:10.3390/ijms232012250 · Cited by 39 · see citing works
Visible light-induced transformation of aldehydes to esters, carboxylic anhydrides and amides
Gaspa, S., Raposo, I. A. M., Pereira, L., Mulas, G., Ricci, P. C., Porcheddu, A., & Luca, L. D. (2019) · New Journal of Chemistry · doi:10.1039/c9nj01984g · Cited by 39 · see citing works
In vitro toxicity and genotoxicity assessment of disinfection by‐products, organic N‐chloramines
Laingam, S., Froscio, S. M., Bull, R. J., & Humpage, A. R. (2011) · Environmental and Molecular Mutagenesis · doi:10.1002/em.20684 · Cited by 38 · see citing works
N-chloroamino acids cause oxidative protein modifications in the erythrocyte membrane
Robaszkiewicz, A., Bartosz, G., & Soszyński, M. (2008) · Mechanisms of Ageing and Development · doi:10.1016/j.mad.2008.05.007 · Cited by 38 · see citing works
Snell, J. A., Jandova, J., & Wondrak, G. T. (2022) · Frontiers in Oncology · doi:10.3389/fonc.2022.887220 · Cited by 37 · see citing works
Relative Insignificance of Virus Inactivation during Aluminum Electrocoagulation of Saline Waters
Tanneru, C. T., Jothikumar, N., Hill, V. R., & Chellam, S. (2014) · Environmental Science & Technology · doi:10.1021/es504381f · Cited by 37 · see citing works
A computational study of the chlorination and hydroxylation of amines by hypochlorous acid
Šakić, D., Hanževački, M., Smith, D. M., & Vrček, V. (2015) · Organic & Biomolecular Chemistry · doi:10.1039/c5ob01823d · Cited by 35 · see citing works
Xie, J. H., Xing, H. Y., Meng, L., Zhao, Y. J., Zeng, Q., Xiao, Q., Li, N. B., Xue, P., & Luo, H. Q. (2024) · Analytical Chemistry · doi:10.1021/acs.analchem.4c03839 · Cited by 34 · see citing works
Aggregation-induced emission luminogens for RONS sensing
Dai, J., Duan, C., Huang, Y., Lou, X., Xia, F., & Wang, S. (2019) · Journal of Materials Chemistry B · doi:10.1039/c9tb02310k · Cited by 34 · see citing works
Li, X., Wei, X., Zhang, C., Jin, X., Tang, J., Fan, G.-J., & Zhou, B. (2012) · Food Chemistry · doi:10.1016/j.foodchem.2012.05.043 · Cited by 33 · see citing works
Chlorination effect on the fluorescence of nucleic acid staining dyes
Phe, M.-H., Dossot, M., & Block, J. C. (2004) · Water Research · doi:10.1016/j.watres.2004.05.018 · Cited by 33 · see citing works
Synthesis of imidazole-activated ribonucleotides using cyanogen chloride
Yi, R., Hongo, Y., & Fahrenbach, A. C. (2017) · Chemical Communications · doi:10.1039/c7cc08489g · Cited by 31 · see citing works
Kuttappan-Nair, V., Samson-Thibault, F., & Wagner, J. R. (2009) · Chemical Research in Toxicology · doi:10.1021/tx900268r · Cited by 31 · see citing works
Boecker, D., Zhang, Z., Breves, R., Herth, F. J. F., Krämer, A., & Bulitta, C. (2023) · PubMed Central · doi:10.3205/dgkh000433 · Cited by 35 · see citing works
Jandova, J., Snell, J., Hua, A., Dickinson, S., Fimbres, J., & Wondrak, G. T. (2021) · Redox Biology · doi:10.1016/j.redox.2021.102042 · Cited by 30 · see citing works
Sernoskie, S. C., Jee, A., & Uetrecht, J. (2023) · International Journal of Molecular Sciences · doi:10.3390/ijms24021243 · Cited by 30 · see citing works
Xia, W., Yuan, Y., Shen, S., Zhu, Y., Wang, Y., Hou, Y., Huang, B., Tian, M., & Feng, F. (2024) · Journal of Food Composition and Analysis · doi:10.1016/j.jfca.2024.106053 · Cited by 30 · see citing works
Potential role of organic sulfur compounds from Allium species in cancer prevention and therapy
Scherer, C., Jacob, C., Dicato, M. A., & Diederich, M. F. (2009) · Phytochemistry Reviews · doi:10.1007/s11101-009-9122-z · Cited by 31 · see citing works
Boncler, M. A., Kehrel, B. E., Szewczyk, R., Stec‐Martyna, E., Bednarek, R., Brodde, M. F., & Watała, C. W. (2017) · International Journal of Biological Macromolecules · doi:10.1016/j.ijbiomac.2017.10.159 · Cited by 33 · see citing works
Discovery and Synthesis of New UV-Induced Intrastrand C(4−8)G and G(8−4)C Photolesions
Münzel, M., Szeibert, C., Glas, A. F., Globisch, D., & Carell, T. (2011) · Journal of the American Chemical Society · doi:10.1021/ja111304f · Cited by 28 · see citing works
Chen, W., Xu, W., Xing, J., Liu, Q., Wang, J., Meng, M., Sheng, J., Xiao, Q., Zeng, L., & Yang, L. (2024) · Analytical Chemistry · doi:10.1021/acs.analchem.3c05056 · Cited by 29 · see citing works
Poly(ADP-Ribose) Polymerase Inhibition Improves Endothelial Dysfunction Induced by Hypochlorite
Radovits, T., Zotkina, J., Lin, L.-N., Bömicke, T., Arif, R., Gerő, D., Horvath, E. M., Karck, M., Szabó, C., & Szabo, G. B. (2007) · Experimental Biology and Medicine · doi:10.3181/0701-rm-16 · Cited by 29 · see citing works
Reactivity of Viral Nucleic Acids with Chlorine and the Impact of Virus Encapsidation
Qiao, Z., Ye, Y., Szczuka, A., Harrison, K. R., Dodd, M. C., & Wigginton, K. R. (2021) · Environmental Science & Technology · doi:10.1021/acs.est.1c04239 · Cited by 29 · see citing works
Reactivity of Nucleic Acid Radicals
Greenberg, M. M. (2016) · Advances in physical organic chemistry · doi:10.1016/bs.apoc.2016.02.001 · Cited by 28 · see citing works
Massicotte, R., Mafu, A. A., Ahmad, D., Deshaies, F., Pichette, G., & Belhumeur, P. (2017) · Frontiers in Microbiology · doi:10.3389/fmicb.2017.00112 · Cited by 28 · see citing works
Zhang, X., Zhang, F., Chai, J., Yang, B., & Liu, B. (2021) · Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy · doi:10.1016/j.saa.2021.119735 · Cited by 27 · see citing works
A new concern raised from algal bloom: Organic chloramines in chlorination
Li, X., Zhai, H., Luo, J., & Hou, R. (2024) · Water Research · doi:10.1016/j.watres.2024.121894 · Cited by 26 · see citing works
Pietrofesa, R. A., Park, K., Mishra, O. P., Johnson‐McDaniel, D., Myerson, J. W., Shuvaev, V. V., Arguiri, E., Chatterjee, S., Moorthy, G. S., Zuppa, A. F., et al. (2021) · International Journal of Molecular Sciences · doi:10.3390/ijms22179477 · Cited by 26 · see citing works
Bastin, G., Loison, P., Vernex‐Loset, L., Dupire, F., Challant, J., Majou, D., Boudaud, N., Krier, G., & Gantzer, C. (2020) · Frontiers in Microbiology · doi:10.3389/fmicb.2020.01157 · Cited by 25 · see citing works
Paumann-Page, M., Kienzl, N. F., Motwani, J., Bathish, B., Paton, L. N., Magon, N. J., Sevcnikar, B., Furtmüller, P. G., Traxlmayr, M. W., Obinger, C., et al. (2021) · Redox Biology · doi:10.1016/j.redox.2021.102090 · Cited by 25 · see citing works
Ratiometric two-photon fluorescent probe for detection of hypochlorite in living cells
Li, Q., Zhan, Z., Zhang, K., Song, H., & Lv, Y. (2020) · Talanta · doi:10.1016/j.talanta.2020.121099 · Cited by 25 · see citing works
Dickerhof, N., Schindler, L., Bernhagen, J., Kettle, A. J., & Hampton, M. B. (2015) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2015.09.009 · Cited by 25 · see citing works
Guerreiro‐Tanomaru, J. M., Morgental, R. D., Flumignan, D. L., Gasparini, F., de Oliveira, J. E., & Tanomaru‐Filho, M. (2011) · Oral Surgery Oral Medicine Oral Pathology Oral Radiology and Endodontology · doi:10.1016/j.tripleo.2011.01.009 · Cited by 24 · see citing works
Zheng, L., Grießer, M., Pratt, D. A., & Greenberg, M. M. (2017) · The Journal of Organic Chemistry · doi:10.1021/acs.joc.7b00093 · Cited by 24 · see citing works
Synthesis and Characterization of Oligonucleotides Containing 5-Chlorocytosine
Kang, J. I., Burdzy, A., Liu, P., & Sowers, L. C. (2004) · Chemical Research in Toxicology · doi:10.1021/tx0498962 · Cited by 24 · see citing works
Mishra, O. P., Popov, A. V., Pietrofesa, R. A., & Christofidou‐Solomidou, M. (2016) · Biochimica et Biophysica Acta (BBA) - General Subjects · doi:10.1016/j.bbagen.2016.05.037 · Cited by 23 · see citing works
Evaluation by Flow Cytometry of Escherichia coli Viability in Lettuce after Disinfection
Teixeira, P., Fernandes, B., Silva, A. M., Dias, N., & Azeredo, J. (2019) · Antibiotics · doi:10.3390/antibiotics9010014 · Cited by 23 · see citing works
Nontaleerak, B., Duang-nkern, J., Wongsaroj, L., Trinachartvanit, W., Romsang, A., & Mongkolsuk, S. (2020) · Applied and Environmental Microbiology · doi:10.1128/aem.01480-20 · Cited by 23 · see citing works
Liu, Z. (2003) · Nucleic Acids Research · doi:10.1093/nar/gkg736 · Cited by 23 · see citing works
Zhang, X., Zhang, F., Yang, B., & Liu, B. (2021) · Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy · doi:10.1016/j.saa.2021.119827 · Cited by 22 · see citing works
Cook, G. M. W., Rothenberger, J. P., Sikaroodi, M., Gillevet, P. M., Peters, E. C., & Jonas, R. B. (2013) · Coral Reefs · doi:10.1007/s00338-012-0989-6 · Cited by 22 · see citing works
Maurel, V., Ravanat, J., & Gambarelli, S. (2006) · Rapid Communications in Mass Spectrometry · doi:10.1002/rcm.2579 · Cited by 22 · see citing works
Nanoformulation approach for improved stability and efficiency of lactoperoxidase
El‐Fakharany, E. M. (2020) · Preparative Biochemistry & Biotechnology · doi:10.1080/10826068.2020.1848866 · Cited by 20 · see citing works
- Authors
- Hawkins, C. L., & Davies, M. J.
- Affiliations
- The Heart Research Institute (AU)
- Corresponding author
- Davies, Michael J.
- Venue
- Chemical Research in Toxicology
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-01-01
- Volume
- 15
- Issue
- 1
- Pages
- 83-92
- ISSN
- 0893-228X (ISSN-L)
- 1520-5010
- OpenAlex
- W1968306408
- Cited by
- 208
- References
- 9
- Citations by year
- 2026: 7 · 2025: 14 · 2024: 18 · 2023: 18 · 2022: 12 · 2021: 17 · 2020: 17 · 2019: 12 · 2018: 5 · 2017: 13 · 2016: 4 · 2015: 3 · 2014: 6 · 2013: 6 · 2012: 6
- FWCI
- 1.42
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Chemical Research in Toxicology (publishedVersion)
- PubMed (publishedVersion)
- Research at the University of Copenhagen (University of Copenhagen) (publishedVersion)
- Topics
- Life Sciences › Immunology and Microbiology › Immunology › Neutrophil, Myeloperoxidase and Oxidative Mechanisms
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Bioactive Compounds and Antitumor Agents
- Keywords
- hypochlorite, DNA damage, RNA damage, polynucleotides, chloramines, nitrogen-centered radicals, myeloperoxidase, neutrophils, monocytes, chronic inflammation, radical formation, pyrimidine dimers, DNA strand breaks, plasmid DNA, 2'-deoxycytidine, 2'-deoxyadenosine, EPR spin trapping
- MeSH terms
- Chloramines, DNA, DNA Damage, Electron Spin Resonance Spectroscopy, Hypochlorous Acid, Polynucleotides, RNA
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
