Design and Synthesis of Fluorinated Amphiphile as 19F MRI/Fluorescence Dual-Imaging Agent by Tuning the Self-Assembly

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• 作者：Shaowei Bo ; Cong Song ; Yu Li ; Weijiang Yu ; Shizhen Chen ; Xin Zhou ; Zhigang Yang ; Xing Zheng ; Zhong-Xing Jiang
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：June 19, 2015
• 年：2015
• 卷：80
• 期：12
• 页码：6360-6366
• 全文大小：626K
• ISSN：1520-6904

文摘

Both ¹⁹F MRI and optical imaging are powerful noninvasive molecular imaging modalities in biomedical applications. To integrate these two complementary imaging modalities, the design and synthesis of a novel ¹⁹F MRI/fluorescence dual-modal imaging agent is reported herein. Through Sonogashira coupling reaction between the fluorinated phenylacetylene and 1,2,4,5-tetraiodobenzene, a fluorophore with 48 symmetrical fluorines at its periphery was constructed with high efficacy. High aqueous solubility was achieved by PEGylation of the fluorophore with monodisperse PEGs. However, an unexpected self-assembly of the PEGylated amphiphilic fluorophore in water 鈥渢urned off鈥?the ¹⁹F NMR signal. However, hydrogenation of the triple bonds or introduction of branched monodisperse PEGs was able to efficiently tune the self-assembly, resulting in the 鈥渢urning on鈥?of the ¹⁹F NMR signal. One of these amphiphiles combines the advantages of label-free fluorescence, high ¹⁹F MRI sensitivity, biocompatibility, and excellent aqueous solubility. The results demonstrate the great potential of such amphiphiles for real-time ¹⁹F MRI and fluorescence dual-modality imaging.