Photochemical Properties of Ofloxacin Involved in Oxidative DNA Damage: A Comparison with Rufloxacin
Abstract
Photodegradation of ofloxacin (OFX) under aerobic conditions gives rise to N-demethylation, mainly involving coupling of radical cation OFX(*)(+ )()with superoxide radical anion. Although H(2)O(2) is produced as a byproduct, oxidative damage to DNA to give 8-OH-dGuo is associated with a type II mechanism. When the photosensitizing potentials of OFX and rufloxacin (RFX) are compared under the same conditions, the latter is shown to produce a much higher degree of DNA oxidation despite the close structural similarity. This is explained by a decrease of the triplet energy when sulfur instead of oxygen is attached to position 8 of the fluoroquinolone ring system. As a consequence, phosphate anions are able to quench OFX triplet but not RFX triplet; this reveals that the reaction medium has a strong influence on the photochemistry of OFX and hence on its photobiological properties.
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Ofloxacin oxidizes DNA predominantly through the Type II mechanism, as also shown for norfloxacin.
“It was subsequently confirmed that ofloxacin oxidized predominantly DNA mostly through the Type II mechanism (177) as also shown for norfloxacin (178).”
From Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup> (2012) · cites this paper as [177]
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Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions<sup>†</sup>
Cadet, J., Mouret, S., Ravanat, J., & Douki, T. (2012) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.2012.01200.x · Cited by 300 · see citing works
Rufloxacin-induced photosensitization in yeast
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Self-citationRufloxacin induced photosensitization in bio-models of increasing complexity
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Self-citationSerrentino, M.-E., Catalfo, A., Angelin, A.-R., de Guidi, G., & Sage, E. (2010) · Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis · doi:10.1016/j.mrfmmm.2010.07.011 · Cited by 9 · see citing works
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- Authors
- Cuquerella, M. C., Boscá, F., Miranda, M. A., Belvedere, A., Catalfo, A., & de Guidi, G.
- Affiliations
- University of Catania (IT)
- Departamento de Química/Instituto de Tecnología Química UPV-CSIC, Universidad Politécnica de Valencia, Valencia, Spain, and Dipartimento di Scienze Chimiche, Università di Catania, Catania, Italy
- Corresponding author
- Miranda, Miguel A.
- Venue
- Chemical Research in Toxicology
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-03-29
- Volume
- 16
- Issue
- 4
- Pages
- 562-570
- ISSN
- 0893-228X (ISSN-L)
- 1520-5010
- OpenAlex
- W2090689000
- Cited by
- 53
- References
- 13
- Citations by year
- 2025: 3 · 2024: 1 · 2022: 1 · 2019: 3 · 2018: 2 · 2015: 6 · 2014: 4 · 2013: 3 · 2012: 5
- FWCI
- 2.95
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Chemical Research in Toxicology (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Bioactive Compounds and Antitumor Agents
- Health Sciences › Medicine › Pulmonary and Respiratory Medicine › Photodynamic Therapy Research Studies
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Carcinogens and Genotoxicity Assessment
- Keywords
- ofloxacin, rufloxacin, fluoroquinolones, photodegradation, oxidative DNA damage, 8-oxoguanine, superoxide, radical cations, hydrogen peroxide, photosensitization, triplet energy, sulfur substitution, phototoxicity
- MeSH terms
- Anti-Bacterial Agents, DNA Damage, Fluorescence, Hydrogen Peroxide, Lasers, Oxidation-Reduction, Photochemistry, Time Factors, Ofloxacin, Quinolones, Fluoroquinolones
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