Design and Synthesis of Fluorinated Amphiphile as 19F MRI/Fluorescence Dual-Imaging Agent by Tuning the Self-Assembly
Design and Synthesis of Fluorinated Amphiphile as 19F MRI/Fluorescence Dual-Imaging Agent by Tuning the Self-Assembly
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DOI：
10.1021/acs.joc.5b00810
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发表时间：
2015-06-19
影响因子：
3.6
通讯作者：
Jiang, Zhong-Xing
中科院分区：
文献类型：
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作者：
Bo, Shaowei;Song, Cong;Jiang, Zhong-Xing
F-19磁共振成像和光学成像在生物医学应用中都是强大的非侵入性分子成像手段。为了整合这两种互补的成像模式，本文报道了一种新型的F-19MRI/荧光双模式显像剂的设计和合成。通过氟化苯乙炔与1，2，4，5-四碘苯的Sonogashira偶联反应，构建了一个外围含48个对称氟的高效荧光团。通过聚乙二醇单分散聚乙二醇单分散聚乙二醇化荧光团获得了高的水溶解度。然而，聚乙二醇化的两亲性荧光团在水中意外的自组装“关闭”了F-19核磁共振信号。然而，三键的氢化或支化单分散钉的引入能够有效地调节自组装，导致F-19核磁共振信号的“开启”。其中一种两亲性化合物结合了无标记荧光、高F-19磁共振灵敏度、生物相容性和优异的水溶解性等优点。结果表明，这种两亲性化合物在实时F-19磁共振成像和荧光双模成像方面具有巨大的潜力。
Both F-19 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 F-19 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 "turned off" the F-19 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 "turning on" of the F-19 NMR signal. One of these amphiphiles combines the advantages of label-free fluorescence, high F-19 MRI sensitivity, biocompatibility, and excellent aqueous solubility. The results demonstrate the great potential of such amphiphiles for real-time F-19 MRI and fluorescence dual-modality imaging.