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Photogeneration of Fluoride by the Fluoroquinolone Antimicrobial Agents Lomefloxacin and Fleroxacin
Author(s) -
Martinez Lydia J.,
Li Galaxy,
Chignell Colin F.
Publication year - 1997
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1997.tb08612.x
Subject(s) - national park , library science , environmental research , lomefloxacin , chemistry , political science , environmental science , geography , archaeology , environmental planning , computer science , ciprofloxacin , ofloxacin , biochemistry , antibiotics
The photolysis (> 320 nm) of the fluoroquinolone antibacterial agents lomefloxacin and fleroxacin results in the loss of their F3 atoms as fluoride. The quantum yield for lomefloxacin was 0.98 at pH 7.4. The mechanism probably involves aryl-F heterolysis from the S1 state with the concomitant generation of a carbene at C-8. In contrast, the monofluorinated fluoroquinolones norfloxacin and ciprofloxacin do not generate fluoride upon irradiation. Carbenes are highly reactive species that undergo addition, insertion and abstraction reactions and can cause DNA cleavage. These findings may explain why lomefloxacin and fleroxacin are more photomutagenic and photocarcinogenic than fluoroquinolones in which C-8 is either unsubstituted or bears a substituent other than fluorine.