Characterization of Lysine−Guanine Cross-Links upon One-Electron Oxidation of a Guanine-Containing Oligonucleotide in the Presence of a Trilysine Peptide
Abstract
Formation of DNA-protein cross-links involving the initial formation of a guanine radical cation was investigated. For this purpose, riboflavin-mediated photosensitization of a TGT oligonucleotide in aerated aqueous solution in the presence of the KKK tripeptide was performed. We have shown that the nucleophilic addition of the epsilon-amino group of the central lysine residue of KKK to the C8 atom of either the guanine radical cation or its deprotonated form gives rise to the efficient formation of a Nepsilon-(guanin-8-yl)-lysine cross-link. Interestingly, the time course of formation of the above-mentioned cross-link was found to be not linear with the time of irradiation, and its formation rapidly reached a plateau. This is explained by secondary decomposition of the initially generated cross-link which could be further oxidized more efficiently than starting TGT oligonucleotide. One-electron oxidation of the initially generated cross-link was found to produce mainly two diastereomeric cross-links exhibiting a spiroimino-trilysine-dihydantoin structure as inferred from enzymatic digestion, CD, UV, NMR and mass spectrometry measurements. In addition, other minor cross-links, for which formation was favored at acidic pH, were assigned as lysine-guanine adducts in which the modified guanine base exhibits a guanidino-trilysine-iminohydantoin structure. A proposed mechanism for the formation of the different detected oligonucleotide-peptide cross-links is given. The high yield of formation of the detected cross-links strongly suggests that a DNA-protein cross-link involving a lysine residue linked to the C8 position of guanine could be generated in cellular systems if a lysine is located in the close vicinity of a guanine radical cation.
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Water reacts efficiently with guanine radical cation, and amino acids with nucleophilic groups including lysine, arginine, and serine covalently bind to C8 of guanine.
“In addition to water that was found initially to efficiently react with Gua •+ (218), several amino acids bearing a nucleophilic group, including lysine, arginine and serine were shown to covalent bind to the C8 of guanine (111,216).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [111]
An alternative mechanism for 6-TG-photosensitized formation of DPCs has been proposed based on reactivity of guanine radical cation with biological nucleophiles.
“An alternative mechanism for the 6-TG-photosensitized formation of DPCs has been recently proposed (216) on the basis of the welldocumented reactivity of Gua •+ , the predominant oneelectron DNA oxidation transient radical formed, with relevant biological nucleophiles (111,134,136,217).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [111]
The central lysine of KKK peptide covalently attaches via its free e-amino group to one-electron oxidation guanine intermediate of TGT trinucleotide.
“A detailed model study of the formation of DPC has shown that the central lysine of KKK peptide was able to undergo highly efficient covalent attachment through its free e-amino group to one-electron oxidation guanine intermediate of the TGT trinucleotide (111) (Fig. 5).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [111]
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- Authors
- Perrier, S., Hau, J., Gasparutto, D., Cadet, J., Favier, A., & Ravanat, J.-L.
- Affiliations
- Université Joseph Fourier (FR)
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2006-04-06
- Volume
- 128
- Issue
- 17
- Pages
- 5703-5710
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2031112625
- Cited by
- 141
- References
- 26
- Citations by year
- 2026: 5 · 2025: 5 · 2024: 6 · 2023: 3 · 2022: 2 · 2021: 5 · 2020: 6 · 2019: 7 · 2018: 7 · 2017: 4 · 2016: 9 · 2015: 4 · 2014: 13 · 2013: 10 · 2012: 14
- FWCI
- 3.39
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- 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
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA Repair Mechanisms
- Keywords
- DNA-protein crosslinks, guanine radical cation, one-electron oxidation, nucleophilic addition
- MeSH terms
- Chromatography, High Pressure Liquid, Electrons, Guanine, Lysine, Oligonucleotides, Oxidation-Reduction, Peptides, Nuclear Magnetic Resonance, Biomolecular, Spectrometry, Mass, Electrospray Ionization
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.
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