O2- photogenerated from aqueous solutions of tetracycline antibiotics (pH 7.3) as evidenced by DMPO spin trapping and cytochrome c reduction.
UV-irradiation of several tetracycline antibiotics in aqueous buffer (pH 7.3) resulted in the generation of the superoxide anion radical (O2-) which was detected by cytochrome c reduction and by spin trapping with 5,5-dimethyl-1-pyrroline-N-oxide and was inhibited by superoxide dismutase. A comparison of the O2- yields from the tetracyclines examined showed the trend chlortetracycline (CTC) greater than oxytetracycline (OXY) greater than demeclocycline (DEM) much greater than (doxycycline (DOXY) = tetracycline (TC) = minocycline (MINO) = 0). This trend is in reasonable agreement with clinical reports that CTC, OXY and DEM are potent photosensitizers, TC is only weakly phototoxic whereas MINO is not. These findings suggest that the O2- production may be involved in tetracycline-induced phototoxicity. While the two methods for O2- detection gave comparable results for most of the tetracyclines, the spin trapping technique was clearly superior for DOXY which reduced cytochrome c in the dark.
D003497:Cyclic N-Oxides; D003574:Cytochrome c Group / Q000378:metabolism*; D004578:Electron Spin Resonance Spectroscopy / Q000379:methods; D010084:Oxidation-Reduction; D012996:Solutions; D013113:Spin Labels; D013329:Structure-Activity Relationship; D013481:Superoxides; D013754:Tetracyclines
D003497:Cyclic N-Oxides; D003574:Cytochrome c Group; D012996:Solutions; D013113:Spin Labels; D013754:Tetracyclines; D013481:Superoxides; C017245:5,5-dimethyl-1-pyrroline-1-oxide