DNA−Protein Cross-Linking from Oxidation of Guanine via the Flash−Quench Technique
Abstract
The production of guanine radicals in DNA via the flash−quench technique is shown to cause the formation of covalent adducts between DNA and histone protein. In the flash−quench experiment, the DNA-bound intercalator Ru(phen) 2 dppz 2+ (phen = 1,10-phenanthroline, dppz = dipyridophenazine) is excited with 442 nm light and quenched oxidatively by Co(NH 3 ) 5 Cl 2+, methyl viologen (MV 2+ ), or Ru(NH 3 ) 6 3+ to produce Ru(phen) 2 dppz 3+, a strong oxidant (+1.6 V) that can oxidize a nearby guanine base (+1.3 V). The guanine radical thus produced is vulnerable to nucleophilic attack and can react with amino acid side chains to form DNA−protein cross-links. Evidence for DNA−protein cross-linking was provided by the chloroform extraction assay, a filter binding assay, and gel electrophoretic analysis. After flash−quench treatment, pUC19 plasmid DNA undergoes a dramatic decrease in mobility that is reversed upon digestion with proteinase K, as seen by agarose gel electrophoresis. In polyacrylamide gel electrophoresis (SDS-PAGE) experiments, the histone protein shows similar mobility shifts. Cross-linking is observed with poly(dG-dC) and mixed sequence DNA, but not with poly(dA-dT), indicating that the reaction requires guanine bases. Measurements of emission quenching indicate that for a given quencher, the amount of cross-linking is correlated to the amount of quenching. When comparing different quenchers, however, the amount of cross-linking is inversely related to the amount of quenching and decreases in the order Co(NH 3 ) 5 Cl 2+ > MV 2+ > Ru(NH 3 ) 6 3+ . This trend in cross-linking correlates instead with the lifetime of the guanine radical measured by transient absorption spectroscopy, and suggests that the cross-linking reaction requires > 100 μs. These results demonstrate that the flash−quench technique is an effective approach for the study of covalent adducts between DNA and protein formed as a result of guanine oxidation, and suggest one possible fate for oxidatively damaged DNA in vivo.
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Independent proofs support covalent attachment of nucleophilic amino acids to guanine radical cation upon one-electron oxidation of oligonucleotides mediated by Type I photosensitizer, flash quench, or biphotonic ionization.
“Other independent proofs that support the covalent attachment of nucleophilic amino acids to Gua •+ upon one-electron oxidation of oligonucleotides mediated by a Type I photosensitizer, the flash quench technique or biphotonic ionization, are available (219-222).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [220]
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- Authors
- Nguyen, K. L., Steryo, M., Kurbanyan, K., Nowitzki, K. M., Butterfield, S. M., Ward, S. R., & Stemp, E. D. A.
- Affiliations
- Mount St. Mary's University (US)
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2000-03-31
- Volume
- 122
- Issue
- 15
- Pages
- 3585-3594
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2068085854
- Cited by
- 59
- References
- 78
- Citations by year
- 2026: 2 · 2025: 1 · 2022: 1 · 2021: 2 · 2020: 1 · 2019: 3 · 2018: 2 · 2017: 1 · 2016: 1 · 2014: 3 · 2013: 3 · 2012: 3
- FWCI
- 1.09
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- 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
- guanine oxidation, guanine radical, histones, cobalt chloride, paraquat, emission quenching, transient absorption spectroscopy, oxidative DNA damage, pUC19 plasmid
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