Endonuclease-sensitive DNA modifications induced by acetone and acetophenone as photosensitizers
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Repair endonucleases, viz. endonuclease III, formamidopyrimidine-DNA glycosylase (FPG protein), endonuclease IV, exonuclease III and UV endonuclease, were used to analyse the modifications induced in bacteriophage PM2 DNA by 333 nm laser irradiation in the presence of acetone or acetophenone. In addition to pyrimidine dimers sensitive to UV endonuclease, 5,6-dihydropyrimidines (sensitive to endonuclease III) and base modifications sensitive to FPG protein were generated. The level of the last in the case of acetone was 50% and in the case of acetophenone 9% of the level of pyrimidine dimers. HPLC analysis of the bases excised by FPG protein revealed that least some of them were 8-hydroxyguanine (7,8-dihydro-8-oxoguanine). In the damage induced by direct excitation of DNA at 254 nm, which was analysed for comparison, the number of FPG protein-sensitive base modifications was only 0.6% of that of the pyrimidine dimers. Mechanistic studies demonstrated that the formation of FPG protein-sensitive modifications did not involve singlet oxygen, as the damage was not increased in D2O as solvent. Hydroxyl radicals, superoxide and H2O2 were also not involved, since the relative number of single strand breaks and of sites of base loss (AP sites) was much lower than in the case of DNA damage induced by hydroxyl radicals and since the presence of SOD or catalase had no effect on the extent of the damage. However, the mechanism did involve an intermediate that was much more efficiently quenched by azide ions than the triplet excited carbonyl compounds and which was possibly a purine radical. Together, the data indicate that excited triplet carbonyl compounds react with DNA not only by triplet-triplet energy transfer yielding pyrimidine dimers, but also by electron transfer yielding preferentially base modifications sensitive to FPG protein, which include 8-hydroxyguanine.
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Several photosensitizers, including acetone, acetophenone, benzophenone, carprofen, fenofibric acid, fluoroquinolones, ketoprofen, and pyridopsoralen derivatives, mediate triplet-triplet energy transfer to form cyclobutane pyrimidine dimers in double-stranded DNA.
“There is an abundant literature on the TTET-mediated formation of CPDs in ds DNA by several photosensitizers, including acetone (142), acetophenone (54,142), benzophenone (54,143), carprofen (144), fenofibric acid (143), fluoroquinolones (92,93,145), ketoprofen (143) and three pyridopsoralen derivatives (146,147).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [142]
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Self-citation
- Authors
- Epe, B., Henzl, H., Adam, W., & Saha-Möller, C. R.
- Affiliations
- University of Würzburg (DE)
- Venue
- Nucleic Acids Research
- Publisher
- Oxford University Press (OUP)
- Published
- 1993
- Volume
- 21
- Issue
- 4
- Pages
- 863-869
- ISSN
- 0305-1048 (ISSN-L)
- 1362-4962
- PMC
- PMC309218
- OpenAlex
- W2022472462
- Cited by
- 33
- References
- 34
- Citations by year
- 2022: 1 · 2021: 1 · 2018: 1 · 2017: 1 · 2016: 1 · 2014: 2 · 2012: 2
- FWCI
- 0.64
- Type
- journal article
- Language
- en
- Open access
- green
- europepmc.org
- Locations
- Nucleic Acids Research (publishedVersion)
- Europe PMC (PubMed Central) (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Funders
- Wilhelm Sander-Stiftung
- Deutsche Forschungsgemeinschaft
- Topics
- 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
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
- Keywords
- acetone, acetophenone, photosensitizers, Fpg protein, 8-oxoguanine, pyrimidine dimers, UV endonuclease, endonuclease III, triplet-triplet energy transfer, electron transfer, DNA damage mechanisms
- MeSH terms
- Acetone, Acetophenones, Animals, Azides, Bacteriophages, Catalase, Cattle, Chromatography, High Pressure Liquid, Deuterium, DNA, DNA Damage, DNA Repair, Guanine, Lasers, N-Glycosyl Hydrolases, Pyrimidine Dimers, Superoxides, Ultraviolet Rays, Water, Photosensitizing Agents, Deuterium Oxide, Sodium Azide, DNA-Formamidopyrimidine Glycosylase
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