Discovery and Synthesis of New UV-Induced Intrastrand C(4−8)G and G(8−4)C Photolesions
Abstract
UV irradiation of cellular DNA leads to the formation of a number of defined mutagenic DNA lesions. Here we report the discovery of new intrastrand C(4-8)G and G(8-4)C cross-link lesions in which the C(4) amino group of the cytosine base is covalently linked to the C(8) position of an adjacent dG base. The structure of the novel lesions was clarified by HPLC-MS/MS data for UV-irradiated DNA in combination with chemical synthesis and direct comparison of the synthetic material with irradiated DNA. We also report the ability to generate the lesions directly in DNA with the help of a photoactive precursor that was site-specifically incorporated into DNA. This should enable detailed chemical and biochemical investigations of these lesions.
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Attempts to find increased 8-oxoGua in cellular S4Thy DNA were unsuccessful, despite S4Thy being an efficient generator of singlet oxygen upon UVA irradiation.
“Attempts to search for an increase in the level of 8-oxoGua in cellular S4Thy DNA were unsuccessful despite the fact that S4Thy is an efficient generator of 1O2 upon UVA irradiation (229).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [229]
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Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup>
Cadet, J., Mouret, S., Ravanat, J., & Douki, T. (2012) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2012.01200.x · Cited by 300 · see citing works
- Authors
- Münzel, M., Szeibert, C., Glas, A. F., Globisch, D., & Carell, T.
- Affiliations
- Center for Integrated Protein Science Munich (DE)
- Corresponding author
- Carell, Thomas
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-03-22
- Volume
- 133
- Issue
- 14
- Pages
- 5186-5189
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2330499970
- Cited by
- 28
- References
- 37
- Citations by year
- 2026: 2 · 2024: 2 · 2023: 3 · 2022: 1 · 2021: 2 · 2020: 1 · 2019: 1 · 2016: 2 · 2015: 2 · 2014: 3 · 2013: 4 · 2012: 1
- FWCI
- 1.56
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA Repair Mechanisms
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Carcinogens and Genotoxicity Assessment
- Keywords
- UV-induced DNA damage, intrastrand cross-links, mutagenic DNA lesions
- MeSH terms
- Cytosine, DNA, Ultraviolet Rays, Photochemical Processes
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