PHOTOREACTION OF 5‐METHOXYPSORALEN WITH THYMIDINE and THE THYMINE MOIETY OF ISOLATED and Saccharomyces cerevisiae DNA. CHARACTERIZATION and MEASUREMENT OF THE TWO cis‐syn FURAN‐SIDE MONOCYCLOADDUCTS
Abstract
The photoreaction of the furan‐side moiety of 5‐methoxypsoralen (5‐MOP) with thymidine used as a DNA model compound was investigated in the dry state. Under these conditions, two main fluorescent photoadducts were formed and isolated by HPLC. The two modified nucleosides were characterized as the two cis‐syn diastereoisomers of furan‐side monoadducts of 5‐MOP to thymidine on the basis of spectroscopic measurements including UV, fluorescence,1 H‐NMR and circular dichroism analysis. The identification and quantification of the latter photoproducts within naked DNA exposed to photoexcited 5‐MOP were achieved by enzymatic digestion completed by HPLC separation and fluorescence detection. Similarly, the two cis‐syn furan‐side monoadducts were found to be formed in the DNA of Saccharomyces cerevisiae cells after incubation with 5‐MOP and subsequent exposure to 365 nm at an incident dose of 38.4 kJ m−2. Under these conditions, the rate of induction of two diastereoisomeric photoadducts was as low as one modification per 10 6 and 2 × 10 5 bases, respectively.
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Two cis-syn diastereomers of 5-MOP furan-side monoadducts to thymidine were measured in S. cerevisiae DNA.
“It may be added that the two cis-syn diastereomers of 5-MOP to the furan-side to thymidine has been also measured in the DNA of S. cerevisiae using the same approach (168).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [168]
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Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup>
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- Authors
- Anselmino, C., Averbeck, D., & Cadet, J.
- Affiliations
- Commissariat à l'Énergie Atomique et aux Énergies Alternatives (FR)
- Centre National de la Recherche Scientifique (FR)
- Corresponding author
- Cadet, Jean
- Venue
- Photochemistry and Photobiology
- Publisher
- Wiley
- Published
- 1995-12
- Volume
- 62
- Issue
- 6
- Pages
- 997-1004
- ISSN
- 0031-8655 (ISSN-L)
- 1751-1097
- OpenAlex
- W2081992730
- Cited by
- 12
- References
- 43
- Citations by year
- 2022: 1 · 2021: 1 · 2016: 1 · 2013: 1 · 2012: 1
- FWCI
- 0.62
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Photochemistry and Photobiology (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 › Cancer Research › Carcinogens and Genotoxicity Assessment
- Health Sciences › Medicine › Pulmonary and Respiratory Medicine › Photodynamic Therapy Research Studies
- Keywords
- 5-methoxypsoralen, thymidine, DNA photoproducts, modified nucleosides
- MeSH terms
- 5-Methoxypsoralen, Animals, Cattle, DNA, Fungal, Methoxsalen, Photochemistry, Saccharomyces cerevisiae, Thymidine, Thymine, DNA Adducts
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