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

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成果类型:
期刊论文
作者:
Bo, Shaowei;Song, Cong;Li, Yu;Yu, Weijiang;Chen, Shizhen;Zhou, Xin;Yang, Zhigang;Zheng, Xing;Jiang, Zhong-Xing
通讯作者:
Zheng, X.
作者机构:
Institute of Pharmacy & Pharmacology, University of South China, Hengyang 421001, China<&wdkj&>Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education and Wuhan University School of Pharmaceutical Sciences, Wuhan 430071, China<&wdkj&>Key Laboratory of Magnetic Resonance in Biological Systems, State Key Laboratory for Magnetic Resonance and Atomic and Molecular Physics, National Center for Magnetic Resonance in Wuhan, Wuhan Institute of Physics and Mathematics, Chinese Academy of Sciences, Wuhan 430071, China<&wdkj&>Hunan Province Cooperative Innovation Center for Molecular Target New Drug Study, Hengyang 421001, China
[Li, Yu; Yu, Weijiang; Jiang, Zhong-Xing; Bo, Shaowei; Song, Cong; Yang, Zhigang] double daggerKey Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education and Wuhan University School of Pharmaceutical Sciences, Wuhan 430071, China
[Jiang, Zhong-Xing; Bo, Shaowei; Zheng, Xing] section signHunan Province Cooperative Innovation Center for Molecular Target New Drug Study, Hengyang 421001, China
[Zhou, Xin; Chen, Shizhen] parallelKey Laboratory of Magnetic Resonance in Biological Systems, State Key Laboratory for Magnetic Resonance and Atomic and Molecular Physics, National Center for Magnetic Resonance in Wuhan, Wuhan Institute of Physics and Mathematics, Chinese Academy of Sciences, Wuhan 430071, China
通讯机构:
[Zheng, Xing] Univ South China, Inst Pharm Pharmacol, Hengyang 421001, Peoples R China.
Institute of Pharmacy and Pharmacology, University of South China, Hengyang, China
语种:
英文
关键词:
Aqueous solubility - Biomedical applications - Dual-modal imaging - Dual-modality imaging - Fluorinated amphiphiles - Imaging modality - Phenylacetylenes - Sonogashira coupling reactions
期刊:
Journal of Organic Chemistry
ISSN:
0022-3263
年:
2015
卷:
80
期:
12
页码:
6360-6366
基金类别:
National Natural Science Foundation of China [21372181, 81227902, 21305156, 81273537]
机构署名:
本校为第一且通讯机构
院系归属:
药学与生物科学学院
摘要:
Both<sup>19</sup>F 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<sup>19</sup>F 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<sup>19</sup>F 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<sup>19</sup>F NMR signal. One of these amphiphiles combines the advantages of label-free fluorescence, high<sup>19</sup>F MRI sensitivity, biocompatibility, and excellent aqueous solubility. The results demonstrate the great potential of such amphiphiles for real-time<sup>19</sup>F MRI and fluorescence dual-modality imaging. &copy;2015 American Chemical Society.

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