A design of fluorescent probes for superoxide based on a nonredox mechanism.
Fluorometric detection of O2-* is performed based on desulfonylation of 3 to the corresponding fluoresceins 4 through nucleophilic substitution, and this fluorescing process is quite specific toward O2-* over H2O2, t-BuOOH, NaOCl, 1O2, HO*, NO*, and ONOO-. Furthermore, effects of glutathione, cytochrome P450 reductase/NADPH, and diaphorase/NADH are relatively small on the fluorescing process of probe 3 with X = Y = F, which is useful to detect O2-* released from neutrophils stimulated by phorbol myristate acetate with satisfactory sensitivity.
Maeda
Hatsuo
H
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan. h-maeda@phs.osaka-u.ac.jp
Yamamoto
Kayoko
K
Nomura
Yoko
Y
Kohno
Iho
I
Hafsi
Leila
L
Ueda
Noritsugu
N
Yoshida
Shoko
S
Fukuda
Masako
M
Fukuyasu
Yuka
Y
Yamauchi
Yuji
Y
Itoh
Norio
N
D001557:Benzenesulfonates / Q000737:chemistry; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry; D015195:Drug Design; D005452:Fluoresceins / Q000138:chemical synthesis / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D005470:Fluorometry; D005978:Glutathione / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000737:chemistry; D019271:Hypoxanthine / Q000737:chemistry; D009249:NADP / Q000737:chemistry; D010084:Oxidation-Reduction; D013451:Sulfonic Acids / Q000737:chemistry; D013482:Superoxide Dismutase / Q000737:chemistry; D013481:Superoxides / Q000032:analysis / Q000737:chemistry*; D014969:Xanthine Oxidase / Q000737:chemistry
D001557:Benzenesulfonates; D005452:Fluoresceins; D005456:Fluorescent Dyes; D013451:Sulfonic Acids; D013481:Superoxides; D019271:Hypoxanthine; C001073:2,4-dinitrobenzenesulfonic acid; D009249:NADP; D003577:Cytochrome P-450 Enzyme System; D006861:Hydrogen Peroxide; D013482:Superoxide Dismutase; D014969:Xanthine Oxidase; D005978:Glutathione