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Cited by 72Photochemistry and Electron Transfer StudiesDNA and Nucleic Acid ChemistryCarcinogens and Genotoxicity Assessment

Comparison of DNA Damage Photoinduced by Ketoprofen, Fenofibric Acid and Benzophenone via Electron and Energy Transfer¶

Lhiaubet, Virginie, Paillous, Nicole, Chouini-Lalanne, Nadia·2007·Photochemistry and Photobiology
DOI 10.1562/0031-8655(2001)0740670coddpb2.0.co2
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Abstract

Ketoprofen (KP) and fenofibrate, respectively, anti-inflammatory and hypolipidemiant agents, promote anormal photosensitivity in patients and may induce photoallergic cross-reactions correlated to their benzophenone-like structure. Here, their ability to photosensitize the degradation of biological targets was particularly investigated in DNA. The photosensitization of DNA damage by KP and fenofibric acid (FB), the main metabolite of fenofibrate, and their parent compound, benzophenone (BZ), was examined on a 32P-end-labeled synthetic oligonucleotide in phosphate-buffered solution using gel sequencing experiments. Upon irradiation at lambda > 320 nm, piperidine-sensitive lesions were induced in single-stranded oligonucleotides by KP, FB and BZ at all G sites to the same extent. This pattern of damage, enhanced in D2O is characteristic of a Type-II mechanism. Spin trapping experiments using 2,2,6,6-tetramethyl-4-piperidone have confirmed the production of singlet oxygen during drug photolysis. On double-stranded oligonucleotides, highly specific DNA break occurred selectively at 5'-G of a 5'-GG-3' sequence, after alkali treatment. Prolonged irradiation led to the degradation of all G residues, with efficiency decreasing in the order 5'-GG > 5'-GA > 5'-GC > 5'-GT, in good agreement with the calculated lowest ionization potentials of stacked nucleobase models supporting the assumption of a Type-I mechanism involving electron transfer, also observed to a lesser extent with adenine. Cytosine sites were also affected but the action of mannitol which selectively inhibited cytosine lesions suggests, in this case, the involvement of hydroxyl radical, also detected by electronic paramagnetic resonance using 5,5-dimethyl-1-pyrrolidine-1-oxide as spin trap. On a double-stranded 32P-end-labeled 25-mer oligonucleotide containing TT and TTT sequences, the three compounds were found to photosensitize by triplet-triplet energy transfer the formation of cyclobutane thymine dimers detected using T4 endonuclease V.

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Crossref · 10.1562/0031-8655(2001)0740670coddpb2.0.co2

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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 [143]

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Authors
Lhiaubet, V., Paillous, N., & Chouini-Lalanne, N.
Affiliations
Université Toulouse III - Paul Sabatier (FR)
Venue
Photochemistry and Photobiology
Publisher
American Society for Photobiology
Published
2007-05-01
Volume
74
Issue
5
Pages
670-678
ISSN
0031-8655 (ISSN-L)
DOI
10.1562/0031-8655(2001)0740670coddpb2.0.co2
OpenAlex
W1930755673
Cited by
72
References
50
Citations by year
2024: 6 · 2023: 1 · 2022: 2 · 2021: 3 · 2020: 3 · 2019: 1 · 2018: 3 · 2017: 1 · 2016: 2 · 2015: 1 · 2014: 5 · 2013: 7 · 2012: 6
FWCI
0.76
Type
journal article
Language
en
Open access
closed
Locations
  • Photochemistry and Photobiology (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
  • 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
Keywords
ketoprofen, fenofibrate, fenofibric acid, benzophenone, photosensitization, DNA damage, singlet oxygen, electron transfer, triplet-triplet energy transfer, cyclobutane thymine dimers, hydroxyl radicals, spin trapping, drug-induced photosensitivity
MeSH terms
Anticholesteremic Agents, Benzophenones, Cytochrome c Group, DNA, DNA Damage, Electron Spin Resonance Spectroscopy, Ketoprofen, Oligodeoxyribonucleotides, Polarography, Fenofibrate, Photosensitizing Agents

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