title: Development of novel fluorescent probe 3-perylene diphenylphosphine for determination of lipid hydroperoxide with fluorescent image analysis.
abstract: A novel fluorescent probe 3-perylene diphenylphosphine (3-PeDPP) was synthesized for the direct analysis of lipid hydroperoxides. The structure of 3-PeDPP was identified by the spectroscopic data, FAB-MS, (1)H NMR, and (13)C NMR. The reactivities of 3-PeDPP with lipid hydroperoxides were investigated in chloroform/MeOH homogeneous solutions and PC liposome model systems oxidized by either 2,2'-azobis(2-amidinopropane)dihydrochloride and photosensitized oxidation. The fluorescence intensity derived from 3-perylene diphenylphosphineoxide (3-PeDPPO) increased proportionally with amount of hydroperoxides produced in homogeneous solutions and liposome model systems. 3-PeDPP was easily incorporated into mouse myeloma SP2 cells and thin tissue section for dynamic membrane lipid peroxidation studies. Linear correlations between fluorescence intensity and amount of hydroperoxides in the cell membrane and tissue sections were obtained. The fluorescence intensity from 2-dimensional image analysis was also well correlated with lipid hydroperoxide level in these models. Thus, the novel probe 3-PeDPP is useful for the direct determination of lipid hydroperoxides in biological materials.
authors.affiliation: Department of Food Science and Technology, Tokyo University of Marine Science and Technology, 5-7 Konan 4, Minato, Tokyo 108-8477, Japan.
authors.forename: Chatchawan
authors.initials: C
authors.lastname: Chotimarkorn
authors.forename: Reiko
authors.initials: R
authors.lastname: Nagasaka
authors.forename: Hideki
authors.initials: H
authors.lastname: Ushio
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Ohshima
authors.forename: Shigeki
authors.initials: S
authors.lastname: Matsunaga
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D005260:Female; D005456:Fluorescent Dyes; D007090:Image Interpretation, Computer-Assisted / Q000379:methods*; D008054:Lipid Peroxides / Q000378:metabolism*; D051379:Mice; D008856:Microscopy, Fluorescence / Q000379:methods*; D009101:Multiple Myeloma / Q000378:metabolism*; D010569:Perylene / Q000031:analogs & derivatives*; D010720:Phosphines
chemical_list: C504951:3-perylene diphenylphosphine; D005456:Fluorescent Dyes; D008054:Lipid Peroxides; D010720:Phosphines; D010569:Perylene