The DOI matches its Crossref record; 76 of the 76 references it cites were found in a registry or an index.
Singlet Oxygen Oxidation of Isolated and Cellular DNA: Product Formation and Mechanistic Insights
Abstract
This survey focuses on recent aspects of the singlet oxygen oxidation of the guanine moiety of nucleosides, oligonucleotides, isolated and cellular DNA that has been shown to be the exclusive DNA target for this biologically relevant photo‐generated oxidant. A large body of mechanistic data is now available from studies performed on nucleosides in both aprotic solvents and aqueous solutions. A common process to both reaction conditions is the formation of 8‐oxo‐7,8‐dihydroguanine by reduction of 8‐hydroperoxyguanine that arises from the rearrangement of initially formed endoperoxide across the 4,8‐bond of the purine moiety. However, in organic solvent the hydroperoxide is converted as a major degradation pathway into a dioxirane that subsequently decomposes into a complex pattern of oxidation products. A different reaction that involved the formation of a highly reactive quinonoid intermediate consecutively to the loss of a water molecule from the 8‐hydroperoxide has been shown to occur in aqueous solution. Subsequent addition of a water molecule at C5 leads to the generation of a spiroiminodihydantoin compound via a rearrangement that involves an acyl shift. However, in both isolated and cellular DNA the latter decomposition pathway is at the best a minor process, because only 8‐oxo‐7,8‐dihydroguanine has been found to be generated. It is interesting to point out that singlet oxygen has been shown to contribute predominantly to the formation of 8‐oxo‐7,8‐dihydroguanine in the DNA of bacterial and human cells upon exposure to UVA radiation. It may be added that the formation of secondary singlet‐oxygen oxidation products of 8‐oxo‐7,8‐dihydroguanine, including spiroiminodihydantoin and oxaluric acid that were characterized in nucleosides and oligonucleotide, respectively, have not yet been found in cellular DNA.
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“The latter intermediate quantitatively rearranges within ds DNA into 8-hydroxyperoxyguanine (39,99) that is further reduced into 8-oxoGua (Fig. 5), the exclusive 1 O 2 oxidation product (39,100,101).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions† (2012) · cites this paper as [39]
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Cites
Ultraviolet radiation-mediated damage to cellular DNA
Cadet, J., Sage, E., & Douki, T. (2005) · Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis · doi:10.1016/j.mrfmmm.2004.09.012 · Cited by 932
Self-citationPhotosensitized Oxidation and Singlet Oxygen: Consequences in Biological Systems
Foote, C. S. (1976) · Elsevier eBooks · doi:10.1016/b978-0-12-566502-5.50010-x · Cited by 829
Oxidative damage to DNA: formation, measurement and biochemical features
Cadet, J., Douki, T., Gasparutto, D., & Ravanat, J. (2003) · Mutation research. Fundamental and molecular mechanisms of mutagenesis · doi:10.1016/j.mrfmmm.2003.09.001 · Cited by 727
Self-citationWavelength dependence of oxidative DNA damage induced by UV and visible light
Kielbassa, C. (1997) · Carcinogenesis · doi:10.1093/carcin/18.4.811 · Cited by 616
Boiteux, S., Gajewski, E., Laval, J., & Dizdaroğlu, M. (1992) · Biochemistry · doi:10.1021/bi00116a016 · Cited by 594
Agar, N., Halliday, G. M., Barnetson, R. S., Ananthaswamy, H. N., Wheeler, M., & Jones, A. M. (2004) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0401141101 · Cited by 536
Mechanisms of formation, genotoxicity, and mutation of guanine oxidation products
Neeley, W. L., & Essigmann, J. M. (2006) · Chemical Research in Toxicology · doi:10.1021/tx0600043 · Cited by 510
Induction of oxidative DNA base damage in human skin cells by UV and near visible radiation
Kvam, E. (1997) · Carcinogenesis · doi:10.1093/carcin/18.12.2379 · Cited by 344
Singlet Oxygen Induces Oxidation of Cellular DNA
Ravanat, J., Mascio, P. D., Martinez, G. R., de Medeiros, M. H. G., & Cadet, J. (2000) · Journal of Biological Chemistry · doi:10.1074/jbc.m006681200 · Cited by 327
Self-citationSinglet-Oxygen Chemiluminescence in Peroxide Reactions
Adam, W., Kazakov, D. V., & Kazakov, V. P. (2005) · Chemical Reviews · doi:10.1021/cr0300035 · Cited by 315
Research works printed but not linked: 3
- Cadet J., 2006, Patai Series: The Chemistry of Functional Groups. The Chemistry of Peroxides, 915
- 10.1562/0031-8655(2003)077<0370:PODMIA>2.0.CO;2 · DOI
- Cadet J., 1990, Bioorganic Photochemistry. Photochemistry and the Nucleic Acids, 1
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Relationships among smoking, oxidative stress, inflammation, macromolecular damage, and cancer
Caliri, A. W., Tommasi, S., & Nia, A. B. (2021) · Mutation Research/Reviews in Mutation Research · doi:10.1016/j.mrrev.2021.108365 · Cited by 750
Singlet Molecular Oxygen Reactions with Nucleic Acids, Lipids, and Proteins
Mascio, P. D., Martinez, G. R., Miyamoto, S., Ronsein, G. E., de Medeiros, M. H. G., & Cadet, J. (2019) · Chemical Reviews · doi:10.1021/acs.chemrev.8b00554 · Cited by 674
Self-citationCadet, J., Douki, T., & Ravanat, J.-L. (2008) · Accounts of Chemical Research · doi:10.1021/ar700245e · Cited by 555
Self-citation
Metadata
- Authors
- Cadet, J., Ravanat, J., Martinez, G. R., Medeiros, M. H. G., & Mascio, P. D.
- Affiliations
- Université Joseph Fourier (FR)
- Universidade de São Paulo (BR)
- Corresponding author
- Cadet, Jean
- Venue
- Photochemistry and Photobiology
- Publisher
- Wiley
- Published
- 2006-09
- Volume
- 82
- Issue
- 5
- Pages
- 1219-1225
- ISSN
- 0031-8655 (ISSN-L)
- 1751-1097
- OpenAlex
- W2175848502
- Cited by
- 176
- References
- 76
- Citations by year
- 2026: 2 · 2025: 3 · 2024: 6 · 2023: 9 · 2022: 7 · 2021: 13 · 2020: 5 · 2019: 10 · 2018: 8 · 2017: 11 · 2016: 14 · 2015: 9 · 2014: 11 · 2013: 5 · 2012: 11
- FWCI
- 0.85
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Photochemistry and Photobiology (publishedVersion)
- PubMed (publishedVersion)
- BioOne Complete (BioOne) (submittedVersion)
- HAL (submittedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Carcinogens and Genotoxicity Assessment
- Physical Sciences › Chemistry › Inorganic Chemistry › Metal-Catalyzed Oxygenation Mechanisms
- Keywords
- singlet oxygen, DNA oxidation, guanine, 8-oxo-7,8-dihydroguanine, dioxiranes, quinonoid intermediate, spiroiminodihydantoin, nucleosides, oligonucleotides, cellular DNA, UVA, reaction mechanism, solvent effects
- MeSH terms
- DNA, Guanine, Guanosine, Nucleosides, Oligonucleotides, Oxidation-Reduction, Solvents, Singlet Oxygen
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