Useful 1O2 (1delta g) generator, 3-(4'-methyl-1'-naphthyl)-propionic acid, 1',4'-endoperoxide (NEPO), for dioxygenation of squalence (a skin surface lipid) in an organic solvent and bacterial killing in aqueous medium.
3-(4'-Methyl-1'-naphthyl)-propionic acid, 1',4'-endoperoxide (NEPO) provides singlet state of oxygen (1O2, 1delta g) at 37 degrees C in sodium phosphate buffer (pH 7.2), acetate buffer (pH 4.5), methanol or chloroform, through the retro-Diels-Alder reaction. The total amount of 1O2 generated by NEPO was calculated using the following equation: [1O2]= [NEPO]0[1-exp(-kt)], where [1O2], [NEPO]0 and k are the total amount of 1O2 produced during the time t, initial concentration of NEPO and the first-order reaction rate constant, respectively. When squalene was exposed to 1O2 which was generated thermolytically from NEPO, it was oxidized to three hydroperoxides, mono-, di- and tri-hydroperoxides, in amounts proportional to the dose of NEPO. The oxidizability of squalene was much more extensive compared with unsaturated phospholipids. Additionally, when wild-type E. coli and lycopene-producing mutant E. coli were exposed to NEPO-derived 1O2, there was significant loss of viability of wild-type E. coli but no significant loss of viability in lycopene-producing strain, suggesting that lycopene by scavenging 1O2 protected E. coli against 1O2 toxicity.
Nakano
M
M
Department of Photon and Free Radical Research, Japan Immunoresearch Laboratories, Takasaki. nakanom@jimro.otsuka.co.jp
Kambayashi
Y
Y
Tatsuzawa
H
H
Komiyama
T
T
Fujimori
K
K
D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry; D002338:Carotenoids / Q000737:chemistry; D004926:Escherichia coli / Q000187:drug effects; D016166:Free Radical Scavengers / Q000737:chemistry; D008054:Lipid Peroxides / Q000737:chemistry*; D000077276:Lycopene; D016877:Oxidants / Q000737:chemistry* / Q000494:pharmacology; D010100:Oxygen / Q000737:chemistry* / Q000494:pharmacology; D011422:Propionates / Q000737:chemistry*; D026082:Singlet Oxygen; D013185:Squalene / Q000737:chemistry; D014867:Water
C114034:3-(4'-methyl-1'-naphthyl)propionic acid 1',4'-endoperoxide; D000900:Anti-Bacterial Agents; D000975:Antioxidants; D016166:Free Radical Scavengers; D008054:Lipid Peroxides; D016877:Oxidants; D011422:Propionates; D014867:Water; D026082:Singlet Oxygen; D002338:Carotenoids; D013185:Squalene; D010100:Oxygen; D000077276:Lycopene