PHOTOSENSITIZATION OF PYRIMIDINES BY 2‐METHYLNAPHTHOQUINONE IN WATER: A LASER FLASH PHOTOLYSIS STUDY
Abstract
2‐Methylnaphthoquinone (MQ) has been excited in water with a 20 ns laser flash at 353 nm and the resultant transient species have been observed optically. Triplet‐state MQ (3 MQ) decays on a sub‐microsecond time scale. It has been characterized in terms of its absorption spectrum and quantum yield. Rate constants have been measured for the decay of 3 MQ in infinitely dilute solution, for self‐quenching by ground‐state MQ, and for reactions of 3 MQ with oxygen, thymine, uracil, 6‐methyluracil, and orotic acid. The interaction of 3 MQ with pyrimidines involves charge transfer to give the pyrimidine cation radical and the MQ : anion radical. These reactions are discussed in relation to the mechanism of pyrimidine photooxidation sensitized by MQ.
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A few photosensitizers, including anthraquinone, benzophenone, 1,4-dimethyl-2-naphthoquinone and riboflavin, can abstract one electron from adenine and pyrimidine bases in addition to guanine.
“A few photosensitizers including anthraquinone (137), benzophenone (138), 1,4-dimethyl-2-naphthoquinone (139) and riboflavin (140) are able to abstract one electron from adenine and pyrimidine bases in addition to guanine.”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [139]
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Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup>
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- Authors
- Fisher, G. J., & Land, E. J.
- Affiliations
- Centre Hospitalier Universitaire de Sherbrooke (CA)
- Cancer Research UK Manchester Institute (GB)
- Venue
- Photochemistry and Photobiology
- Publisher
- Wiley
- Published
- 1983-01
- Volume
- 37
- Issue
- 1
- Pages
- 27-32
- ISSN
- 0031-8655 (ISSN-L)
- 1751-1097
- OpenAlex
- W1996518983
- Cited by
- 72
- References
- 24
- Citations by year
- 2024: 1 · 2021: 1 · 2015: 2 · 2012: 3
- FWCI
- 2.65
- 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 › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Bioactive Compounds and Antitumor Agents
- Health Sciences › Medicine › Pulmonary and Respiratory Medicine › Photodynamic Therapy Research Studies
- Keywords
- triplet state decay, charge transfer, radical anions, thymine, uracil, 6-methyluracil, orotic acid, oxygen quenching, self-quenching, quantum yield
- MeSH terms
- DNA, Lasers, Naphthoquinones, Photolysis, Pyrimidines, Structure-Activity Relationship, Vitamin K 3
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