Mechanism of action of sensors for reactive oxygen species based on fluorescein-phenol coupling: the case of 2-[6-(4'-hydroxy)phenoxy-3H-xanthen-3-on-9-yl]benzoic acid.
We demonstrate the ability of a sensor containing a tethered fluorescein-phenol structure to react with peroxyl radicals and with an oxidizing agent such as potassium ferricyanide. This latter reaction yields the corresponding peroxyl radical as observed by EPR analysis. We propose that the reaction of the sensor with peroxyl and alkoxyl radicals is also initiated by the formation of the phenoxyl radicals, which is followed by radical-radical reactions and product hydrolysis responsible for the release of fluorescein. The proposed mechanism is based on results obtained by laser flash photolysis, HPLC and EPR studies of the reaction of peroxyl and alkoxyl radicals with 4-phenoxylphenol, a molecule used to mimic the behavior of the sensor.
Heyne
Belinda
B
Department of Chemistry, University of Ottawa, Ottawa K1N 6N5, Canada.
Maurel
Vincent
V
Scaiano
J C
JC
D002623:Chemistry Techniques, Analytical / Q000379:methods*; D004578:Electron Spin Resonance Spectroscopy; D019793:Fluorescein / Q000737:chemistry* / Q000378:metabolism; D005452:Fluoresceins / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry* / Q000378:metabolism; D010636:Phenols / Q000737:chemistry*; D017382:Reactive Oxygen Species / Q000032:analysis*; D013050:Spectrometry, Fluorescence
C520960:2-(6-(4'-hydroxy)phenoxy-3H-xanthen-3-on-9-yl)benzoic acid; D005452:Fluoresceins; D005456:Fluorescent Dyes; D010636:Phenols; D017382:Reactive Oxygen Species; D019793:Fluorescein