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.

Cite this paper

@article{Cuquerella2003PhotochemicalPO, title={Photochemical properties of ofloxacin involved in oxidative DNA damage: a comparison with rufloxacin.}, author={M Consuelo Cuquerella and Francisco Bosc{\'a} and Miguel A Miranda and Alessandra Belvedere and Alfio Catalfo and Guido de Guidi}, journal={Chemical research in toxicology}, year={2003}, volume={16 4}, pages={562-70} }