Quantitative Analysis of DNA Interstrand Cross-Links and Monoadducts Formed in Human Cells Induced by Psoralens and UVA Irradiation
Open accessAbstract
Upon exposure to UVA light, psoralens can induce DNA interstrand cross-links (ICLs), which can block DNA replication and transcription. Among the psoralen derivatives, 8-methoxypsoralen (8-MOP) is conventionally applied for psoriasis therapy, and amotosalen S59 is used to inactivate bacterial and viral pathogens in blood components. In addition to the ICL formation, psoralens also readily form various monoadducts (MAs) with thymidine residues in DNA when exposed to UVA light, and the biological implications for these monoadducts remain unclear. Here, we reported a method that encompassed digestion with a single enzyme (nuclease P1) and LC-MS/MS, for the simultaneous quantification of ICL and MAs induced in human cells exposed with 8-MOP or S59 and UVA light. Our results showed that the yield of ICL induced by S59, which increased from 3.9 to 12.8 lesions/10(3) nucleotides as the dose of UVA light increased from 0.5 to 10.0 J/cm(2), was approximately 100 fold more than that induced by 8-MOP. In addition, three and five products were identified as 8-MOP- and S59-MAs, respectively, and the yields of MAs were significantly lower than that for ICL. The yields of the three 8-MOP-MAs were 7.6-2.2, 1.9-9.9, and 7.2-51 per 10(6) nucleotides and those of the five S59-MAs were 215-19, 106-39, 25-21, 32-146, and 22-26 per 10(6) nucleotides as the dose of UVA light increased from 0.5 to 10.0 J/cm(2). Although the yields of MAs induced by 8-MOP and S59 were lower than those of the respective ICLs under the same exposure conditions, the formation of appreciable amounts of MAs might account for some of the mutations induced by psoralens.
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S59 has up to 2 orders of magnitude higher photoreactivity than 8-MOP.
“A much higher photoreactivity of S59, up to 2 orders of magnitude, with respect to 8-MOP was inferred from the measured levels of monoadducts and ICLs.”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [170]
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Islam, T., Price, N. E., Amin, S. B. M., Yang, Z., Johnson, K. M., Lei, Z., Wang, Y., & Gates, K. S. (2025) · Chemical Research in Toxicology · doi:10.1021/acs.chemrestox.5c00263
Self-citation
- Authors
- Lai, C., Cao, H., Hearst, J. E., Corash, L., Luo, H., & Wang, Y.
- Affiliations
- University of California, Riverside (US)
- Corresponding author
- Luo, Hai
- Wang, Yinsheng
- Venue
- Analytical Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-10-24
- Volume
- 80
- Issue
- 22
- Pages
- 8790-8798
- ISSN
- 0003-2700 (ISSN-L)
- 1520-6882
- PMC
- PMC2626160
- OpenAlex
- W2052260838
- Cited by
- 70
- References
- 26
- Citations by year
- 2026: 1 · 2025: 2 · 2024: 4 · 2023: 1 · 2022: 2 · 2021: 5 · 2020: 3 · 2019: 5 · 2018: 6 · 2017: 3 · 2016: 6 · 2015: 4 · 2014: 6 · 2013: 7 · 2012: 7
- FWCI
- 0.80
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Analytical Chemistry (publishedVersion)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- Funders
- China Scholarship Council
- National Cancer Institute (R01CA101864)
- Topics
- 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
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
- Keywords
- interstrand cross-links, psoralen, 8-methoxypsoralen, UVA irradiation, LC-MS/MS quantification, photodynamic DNA damage, psoriasis treatment, mutagenesis
- MeSH terms
- Animals, Base Sequence, Cattle, Cross-Linking Reagents, DNA, DNA Damage, Humans, Methoxsalen, Oligodeoxyribonucleotides, Furocoumarins, Ultraviolet Rays, Cell Line, Tumor
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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