Cited by 28DNA and Nucleic Acid ChemistryDNA Repair MechanismsCarcinogens and Genotoxicity Assessment

Discovery and Synthesis of New UV-Induced Intrastrand C(4−8)G and G(8−4)C Photolesions

Münzel, Martin, Szeibert, Claudia, Glas, Andreas F., Globisch, Daniel, Carell, Thomas·2011·Journal of the American Chemical Society

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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Crossref · 10.1021/ja111304f

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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).”

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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
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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