title: Design and Synthesis of Fluorinated Amphiphile as (19)F MRI/Fluorescence Dual-Imaging Agent by Tuning the Self-Assembly.
abstract: Both (19)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 (19)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 (19)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 (19)F NMR signal. One of these amphiphiles combines the advantages of label-free fluorescence, high (19)F MRI sensitivity, biocompatibility, and excellent aqueous solubility. The results demonstrate the great potential of such amphiphiles for real-time (19)F MRI and fluorescence dual-modality imaging.
authors.affiliation: ‡Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education and Wuhan University School of Pharmaceutical Sciences, Wuhan 430071, China.|§Hunan Province Cooperative Innovation Center for Molecular Target New Drug Study, Hengyang 421001, China.
authors.forename: Shaowei
authors.initials: S
authors.lastname: Bo
authors.affiliation: ‡Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education and Wuhan University School of Pharmaceutical Sciences, Wuhan 430071, China.
authors.forename: Cong
authors.initials: C
authors.lastname: Song
authors.affiliation: ‡Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education and Wuhan University School of Pharmaceutical Sciences, Wuhan 430071, China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Li
authors.affiliation: ‡Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education and Wuhan University School of Pharmaceutical Sciences, Wuhan 430071, China.
authors.forename: Weijiang
authors.initials: W
authors.lastname: Yu
authors.affiliation: ∥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.
authors.forename: Shizhen
authors.initials: S
authors.lastname: Chen
authors.affiliation: ∥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.
authors.forename: Xin
authors.initials: X
authors.lastname: Zhou
authors.affiliation: ‡Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education and Wuhan University School of Pharmaceutical Sciences, Wuhan 430071, China.
authors.forename: Zhigang
authors.initials: Z
authors.lastname: Yang
authors.affiliation: §Hunan Province Cooperative Innovation Center for Molecular Target New Drug Study, Hengyang 421001, China.
authors.forename: Xing
authors.initials: X
authors.lastname: Zheng
authors.affiliation: ‡Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education and Wuhan University School of Pharmaceutical Sciences, Wuhan 430071, China.|§Hunan Province Cooperative Innovation Center for Molecular Target New Drug Study, Hengyang 421001, China.
authors.forename: Zhong-Xing
authors.initials: ZX
authors.lastname: Jiang
mesh_terms: D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D054879:Halogenation; D008279:Magnetic Resonance Imaging; D061848:Optical Imaging; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D005456:Fluorescent Dyes; D013501:Surface-Active Agents