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

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• 作者：Yuji Fujita ; Yoshihiro Murakami ; Akihiro Noda ; Sosuke Miyoshi
• 刊名：Bioconjugate Chemistry
• 出版年：2017
• 出版时间：February 15, 2017
• 年：2017
• 卷：28
• 期：2
• 页码：642-648
• 全文大小：382K
• ISSN：1520-4812

文摘

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.