18F-Fluorothiols: A New Approach To Label Peptides Chemoselectively as Potential Tracers for Positron Emission Tomography

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• 作者：Matthias Glaser ; Hege Karlsen ; Magne Solbakken ; Joseph Arukwe ; Frank Brady ; Sajinder K. Luthra ; and Alan Cuthbertson
• 刊名：Bioconjugate Chemistry
• 出版年：2004
• 出版时间：November 2004
• 年：2004
• 卷：15
• 期：6
• 页码：1447 - 1453
• 全文大小：116K
• 年卷期：v.15,no.6(November 2004)
• ISSN：1520-4812

文摘

[¹⁸F]Fluorothiols are a new generation of peptide labeling reagents. This article describes thepreparation of suitable methanesulfonyl precursors and their use in no-carrier-added radiosynthesesof ¹⁸F-fluorothiols. The preparations of (3-[¹⁸F]fluoropropylsulfanyl)triphenylmethane, (2-{2-[2-(2-[¹⁸F]fluoroethoxy)ethoxy]ethoxy}ethylsulfanyl)triphenylmethane, and 4-[¹⁸F]fluoromethyl-N-[2-triphenylmethanesulfanyl)ethyl]benzamide starting from the corresponding methanesulfonyl precursors wereinvestigated. Following the removal of the triphenylmethane protecting group, the ¹⁸F-fluorothiolswere reacted with the N-terminal chloroacetylated model peptide ClCH₂C(O)-LysGlyPheGlyLys. Thecorresponding radiochemical yields of ¹⁸F-labeled isolated model peptide, decay-corrected to ¹⁸F fluoride,were 10%, 32%, and 1%, respectively. These results indicate a considerable potential of ¹⁸F-fluorothiolsfor the chemoselective labeling of peptides as tracers for positron emission tomography (PET).