Novel Method for Radiolabeling and Dimerizing Thiolated Peptides Using 18F-Hexafluorobenzene

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• 作者：Orit Jacobson ; Xuefeng Yan ; Ying Ma ; Gang Niu ; Dale O. Kiesewetter ; Xiaoyuan Chen
• 刊名：Bioconjugate Chemistry
• 出版年：2015
• 出版时间：October 21, 2015
• 年：2015
• 卷：26
• 期：10
• 页码：2016-2020
• 全文大小：287K
• ISSN：1520-4812

文摘

Hexafluorobenzene (HFB) reacts with free thiols to produce a unique and selective perfluoroaromatic linkage between two sulfurs. We modified this chemical reaction to produce dimeric ¹⁸F-RGD-tetrafluorobenzene (TFB)-RGD, an integrin 伪_v尾₃ receptor ligand. ¹⁸F-HFB was prepared by a fluorine exchange reaction using K¹⁸F/K_2.2.2 at room temperature. The automated radiofluorination was optimized to minimize the amount of HFB precursor and, thus, maximize the specific activity. ¹⁸F-HFB was isolated by distillation and subsequently reacted with thiolated c(RGDfk) peptide under basic and reducing conditions. The resulting ¹⁸F-RGD-TFB-RGD demonstrated integrin receptor specific binding, cellular uptake, and in vivo tumor accumulation.¹⁸F-HFB can be efficiently incorporated into thiol-containing peptides at room temperature to provide novel imaging agents.