title: Design and Synthesis of an Easily Obtainable Maleimide Reagent N-[2-(4-[18F]fluoro-N-methylbenzenesulfonamido)ethyl]maleimide ([18F]FBSEM) to Radiolabel Thiols in Proteins.
abstract: An easily obtainable thiol-selective labeling reagent [18F]FBSEM (N-[2-(4-[18F]fluoro-N-methylbenzenesulfonamido)ethyl]maleimide) was developed. The advantage of the design is that the precursor and [18F]FBSEM have the same backbone and backbone construction is not required; in contrast, known thiol-specific labeling reagents do require backbone construction, and this is thought to be the cause of their complicated synthesis. [18F]FBSEM was successfully obtained in higher yield (25%) and in a simpler way (two fluorination and deprotection steps in 65 min) than the widely used [18F]FBEM (N-[2-(4-[18F]fluorobenzamide)ethyl]maleimide). The labeling efficacy of [18F]FBSEM was confirmed by conjugation with glutathione. [18F]FBSEM is a promising labeling agent for proteins.
authors.affiliation: Drug Discovery Research, Astellas Pharma Inc. , Tsukuba 305-8585, Japan.
authors.forename: Yuji
authors.initials: Y
authors.lastname: Fujita
authors.affiliation: Drug Discovery Research, Astellas Pharma Inc. , Tsukuba 305-8585, Japan.
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Murakami
authors.affiliation: Drug Discovery Research, Astellas Pharma Inc. , Tsukuba 305-8585, Japan.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Noda
authors.affiliation: Drug Discovery Research, Astellas Pharma Inc. , Tsukuba 305-8585, Japan.
authors.forename: Sosuke
authors.initials: S
authors.lastname: Miyoshi
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry; D061565:Cycloaddition Reaction; D005462:Fluorine Radioisotopes / Q000737:chemistry*; D005978:Glutathione / Q000031:analogs & derivatives*; D054879:Halogenation; D007202:Indicators and Reagents; D007553:Isotope Labeling; D008301:Maleimides / Q000737:chemistry*; D011506:Proteins / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D001555:Benzene Derivatives; D005462:Fluorine Radioisotopes; D007202:Indicators and Reagents; D008301:Maleimides; D011506:Proteins; D013438:Sulfhydryl Compounds; D005978:Glutathione