期刊论文

Zheng, X.

英文

Journal of Organic Chemistry

0022-3263

2015

80

12

6360-6366

10.1021/acs.joc.5b00810

National Natural Science Foundation of China [21372181, 81227902, 21305156, 81273537]

本校为第一且通讯机构

Both¹⁹F 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 novel¹⁹F 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" the¹⁹F 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 the¹⁹F NMR signal. One of these amphiphiles combines the advantages of label-free fluorescence, high¹⁹F MRI sensitivity, biocompatibility, and excellent aqueous solubility. The results demonstrate the great potential of such amphiphiles for real-time¹⁹F MRI and fluorescence dual-modality imaging. ©2015 American Chemical Society.