title: Synthesis and characterization of fluorinated homocysteine derivatives as potential molecular probes for ¹⁹F magnetic resonance spectroscopy and imaging.
abstract: A N-trifluoroacetyl-protected amino acid containing a thioester function, 2,2,2-trifluoro-N-(2-oxo-tetrahydrothiophen-3-yl)acetamide (TFA-tHcy), has been synthesized and characterized. It was then used to prepare a fluorine-labeled N-homocysteinylated protein, (19)F-Hcy-εN-Lys-albumin, that was characterized by SDS-PAGE, MALDI-TOF-MS, UV-vis and (19)F NMR spectroscopy. On average, four N-trifluoroacetylhomocysteine residues were covalently conjugated to human serum albumin through the N-substituted homocysteine thiolactone. The in situ homocysteinylation of human plasma proteins with TFA-tHcy has also been performed and has led to the formation of N-homocysteinylated proteins, with albumin modification accounting for ca. 75% of all fluorine-labeled human plasma proteins. The synthesized fluorinated molecular probes can be potentially used as informative molecular probes for in vivo (19)F magnetic resonance spectroscopy and imaging.
authors.affiliation: Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, 630090 Novosibirsk, Russia.
authors.forename: Alexey S
authors.initials: AS
authors.lastname: Chubarov
authors.forename: Makhmut M
authors.initials: MM
authors.lastname: Shakirov
authors.forename: Igor V
authors.initials: IV
authors.lastname: Koptyug
authors.forename: Renad Z
authors.initials: RZ
authors.lastname: Sagdeev
authors.forename: Dmitry G
authors.initials: DG
authors.lastname: Knorre
authors.forename: Tatyana S
authors.initials: TS
authors.lastname: Godovikova
mesh_terms: D004591:Electrophoresis, Polyacrylamide Gel; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D006710:Homocysteine / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D005456:Fluorescent Dyes; D006710:Homocysteine