title: Luminescent rhenium(I) polypyridine fluorous complexes as novel trifunctional biological probes.
abstract: We present the synthesis, characterization, and photophysical properties of three luminescent rhenium(I) polypyridine fluorous complexes [Re(Me(2)bpy)(CO)(3)(L)](PF(6)) (Me(2)bpy = 4,4'-dimethyl-2,2'-bipyridine; L = 3-amino-5-(N-((3-perfluorooctyl)propyl)aminocarbonyl)pyridine (py-Rf-NH(2)) (1), 3-isothiocyanato-5-(N-((3-perfluorooctyl)propyl)aminocarbonyl)pyridine (py-Rf-NCS) (2), 3-ethylthioureidyl-5-(N-((3-perfluorooctyl)propyl)aminocarbonyl)pyridine (py-Rf-TU-C(2)H(5)) (3)). The isothiocyanate complex 2 has been used to label bovine serum albumin (BSA) and glutathione (GSH). The photophysical properties of the resultant bioconjugates have been studied. The isolation of the luminescent fluorous rhenium-GSH conjugate from a mixture of 20 amino acids has been demonstrated using fluorous solid-phase extraction (FSPE). Additionally, the cytotoxicity of complexes 1 and 3 toward HeLa cells has been examined by the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyltetrazolium bromide (MTT) assay. The cellular uptake properties of complex 3 have also been investigated by laser-scanning confocal microscopy.
authors: Department of Biology and Chemistry, City University of Hong Kong, Tat Chee Avenue, Kowloon, Hong Kong, PR China.
authors: Man-Wai
authors: MW
authors: Louie
authors: Tommy Tsz-Him
authors: TT
authors: Fong
authors: Kenneth Kam-Wing
authors: KK
authors: Lo
mesh_terms: D002470:Cell Survival / Q000187:drug effects; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D005562:Formazans / Q000737:chemistry; D005978:Glutathione / Q000302:isolation & purification; D006367:HeLa Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D018613:Microscopy, Confocal; D008958:Models, Molecular; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D012211:Rhenium / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared; D013778:Tetrazolium Salts / Q000737:chemistry
chemical_list: D056831:Coordination Complexes; D005456:Fluorescent Dyes; D005562:Formazans; D011725:Pyridines; D013778:Tetrazolium Salts; C079782:MTT formazan; D012211:Rhenium; D005978:Glutathione