Synthesis of N4′-[18F]Fluoroalkylated Ciprofloxacin as a Potential Bacterial Infection Imaging Agent for PET Study

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• 作者：Kalme Sachin ; Eun-Mi Kim ; Su-Jin Cheong ; Hwan-Jeong Jeong ; Seok Tae Lim ; Myung-Hee Sohn ; Dong Wook Kim
• 刊名：Bioconjugate Chemistry
• 出版年：2010
• 出版时间：December 15, 2010
• 年：2010
• 卷：21
• 期：12
• 页码：2282-2288
• 全文大小：246K
• 年卷期：v.21,no.12(December 15, 2010)
• ISSN：1520-4812

文摘

Syntheses and evaluation of fluoroalkylated ciprofloxacin analogues are described. Among these analogues, N₄′-3-fluoropropylciprofloxacin (16) showed the most efficient antibacterial activity against E. coli strains (DH5α and TOP10) and a high binding affinity for DNA gyrase of bacteria. To develop bacteria-specific infection imaging agents for positron emission tomography (PET), no-carrier-added N₄′-3-[¹⁸F]fluoropropylciprofloxacin ([¹⁸F]16) was prepared in two steps from N₄′-3-methanesufonyloxypropylciprofloxacin, resulting in a 40% radiochemical yield (decay corrected for 100 min) via the tert-alcohol media radiofluorination protocol with high radiochemical purity (>99%) as well as high specific activity (149 ± 75 GBq/μmol). The agent was stable (>90%), as shown by an in vitro human serum stability assay. A bacterial uptake and blocking study of [¹⁸F]16 using authentic compound 16 in TOP10 cells demonstrated its high specific bacterial uptake. The results suggest that this radiotracer holds promise as a useful bacterial infection radiopharmaceutical for PET imaging.