Direct Observation and Quantitative Characterization of Singlet Oxygen in Aqueous Solution upon UVA Excitation of 6-Thioguanines
Open accessAbstract
The incorporation of 6-thioguanine (6-TG) into DNA increases the risk of (1)O(2)-initiated skin cancer. We herein provide the first report on quantitative characterization of the photoactivity of 6-thioguanines including 6-TG and 6-thioguanosine. Time-resolved singlet oxygen luminescence was observed directly for the first time after UVA irradiation of 6-thioguanines in both CHCN(3) and aqueous solutions. Their photosensitization was characterized by the quantum yield of singlet oxygen production, showing a dramatic decrease over time from the initial 0.49-0.58 to zero. Experiments performed on both 6-TG and 6-thioguanosine did not show any significant difference in the quantum yield of singlet oxygen production, indicating that there was no potential participation of 7H- and 9H-tautomers. Our findings provide a primary basis for a better understanding of molecular events of thiopurine drugs in biological systems.
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Quantum yields of singlet oxygen generation by UVA-excited 6-TG and related ribonucleosides vary within 0.40-0.58.
“The quantum yields of 1 O 2 generation by UVA-excited 6-TG and related ribonucleosides that were almost simultaneously determined by time-resolution luminescence measurements at 1270 nm were found to vary within the 0.40-0.58range (211).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [211]
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Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup>
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- Authors
- Zhang, Y., Zhu, X., Smith, J., Haygood, M. T., & Gao, R.
- Affiliations
- Jackson State University (US)
- Corresponding author
- Gao, Ruomei
- Venue
- The Journal of Physical Chemistry B
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-02-04
- Volume
- 115
- Issue
- 8
- Pages
- 1889-1894
- ISSN
- 1520-5207 (ISSN-L)
- 1520-6106
- PMC
- PMC3079460
- OpenAlex
- W1966242338
- Cited by
- 53
- References
- 44
- Citations by year
- 2026: 3 · 2025: 5 · 2024: 1 · 2023: 1 · 2021: 6 · 2020: 1 · 2019: 5 · 2018: 4 · 2017: 5 · 2016: 4 · 2015: 2 · 2014: 4 · 2013: 4 · 2012: 3
- FWCI
- 3.40
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- The Journal of Physical Chemistry B (publishedVersion)
- PubMed (publishedVersion)
- Europe PMC (PubMed Central) (acceptedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Institutes of Health
- National Center for Research Resources (G12RR013459)
- Topics
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
- Health Sciences › Medicine › Pulmonary and Respiratory Medicine › Photodynamic Therapy Research Studies
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › DNA and Nucleic Acid Chemistry
- Keywords
- singlet oxygen, 6-thioguanine, 6-thioguanosine, UVA irradiation, photosensitization, quantum yield, time-resolved luminescence, aqueous solutions, tautomerism, DNA damage, skin cancer
- MeSH terms
- Hydrogen-Ion Concentration, Kinetics, Quantum Theory, Solutions, Spectrometry, Fluorescence, Thioguanine, Ultraviolet Rays, Water, Singlet Oxygen
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