Type I lipid photo-oxidation by the nonsteroidal anti-inflammatory drug suprofen: a possible key to its photosensitivity.
A nonsteroidal anti-inflammatory drug suprofen acted as a photosensitizer to oxidize lipids on ultraviolet A irradiation, that is, squalene and cholesterol in ethanol solution and phosphatidylcholine in liposome membranes. Photo-oxidation of squalene sensitized with suprofen was not repressed by the addition of sodium azide. Photo-oxidation of cholesterol sensitized with suprofen produced 7 alpha- and 7 beta-hydroperoxides but not 5 alpha-hydroperoxide of cholesterol. These findings are consistent with the type I mechanism but not the type II mechanism of photo-oxidation. Suprofen-sensitized photo-oxidation of membrane lipids of liposomes increased leakage of trapped glucose, suggesting photosensitized destabilization of the membrane structure. These results suggest that the photo-oxidation ability of suprofen by the type I mechanism is a possible key to the induction of suprofen photosensitivity.
Fujita
H
H
Department of Molecular Life Science, Tokai University School of Medicine, Kanagawa, Japan.
Matsuo
I
I
D002784:Cholesterol / Q000031:analogs & derivatives / Q000032:analysis / Q000737:chemistry*; D005947:Glucose / Q000032:analysis / Q000737:chemistry; D015227:Lipid Peroxidation / Q000528:radiation effects; D008054:Lipid Peroxides / Q000032:analysis; D008081:Liposomes; D010713:Phosphatidylcholines / Q000032:analysis / Q000737:chemistry*; D017319:Photosensitizing Agents / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D013185:Squalene / Q000737:chemistry*; D013496:Suprofen / Q000737:chemistry*; D014466:Ultraviolet Rays
D008054:Lipid Peroxides; D008081:Liposomes; D010713:Phosphatidylcholines; D017319:Photosensitizing Agents; C057590:phosphatidylcholine hydroperoxide; C002843:cholesterol hydroperoxide; D013185:Squalene; D002784:Cholesterol; D013496:Suprofen; D005947:Glucose