Photochemical Properties of Ofloxacin Involved in Oxidative DNA Damage: A Comparison with Rufloxacin
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- 作者：M. Consuelo Cuquerella ; Francisco Boscá ; Miguel A. Miranda ; Alessandra Belvedere ; Alfio Catalfo ; and Guido de Guidi
- 刊名：Chemical Research in Toxicology
- 出版年：2003
- 出版时间：April 2003
- 年：2003
- 卷：16
- 期：4
- 页码：562 - 570
- 全文大小：175K
- 年卷期：v.16,no.4(April 2003)
- ISSN：1520-5010
文摘
Photodegradation of ofloxacin (OFX) under aerobic conditions gives rise to N-demethylation,mainly involving coupling of radical cation OFX
+ with superoxide radical anion. AlthoughH2O2 is produced as a byproduct, oxidative damage to DNA to give 8-OH-dGuo is associatedwith 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 degreeof DNA oxidation despite the close structural similarity. This is explained by a decrease of thetriplet energy when sulfur instead of oxygen is attached to position 8 of the fluoroquinolonering system. As a consequence, phosphate anions are able to quench OFX triplet but not RFXtriplet; this reveals that the reaction medium has a strong influence on the photochemistry ofOFX and hence on its photobiological properties.
+ with superoxide radical anion. AlthoughH2O2 is produced as a byproduct, oxidative damage to DNA to give 8-OH-dGuo is associatedwith 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 degreeof DNA oxidation despite the close structural similarity. This is explained by a decrease of thetriplet energy when sulfur instead of oxygen is attached to position 8 of the fluoroquinolonering system. As a consequence, phosphate anions are able to quench OFX triplet but not RFXtriplet; this reveals that the reaction medium has a strong influence on the photochemistry ofOFX and hence on its photobiological properties.