Fluorine Meets Amine: Reducing Microenvironment-Induced Amino-Activatable Nanoprobes for 19 F-Magnetic Resonance Imaging of Biothiols

ACS Applied Materials & Interfaces
Pingsheng HuangWeiwei Wang

Abstract

19F-magnetic resonance imaging (MRI) is of great significance for noninvasive imaging and detection of various diseases. However, the main obstacle in the application of 19F-MRI agents stems from the unmet signal sensitivity due to the poor water solubility and restricted mobility of segments with high number of fluorine atoms. Herein, we report a kind of intracellular reducing microenvironment-induced amino-activatable 19F-MRI nanoprobe, which can be used for specific imaging of biothiols. In principle, the nanoprobe has an initial architecture of hydrophobic core, where the trifluoromethyl-containing segments are compactly packed and 19F NMR/MRI signals are quenched ("OFF" state). Upon encountering sulfydryl, the strong electron-withdrawing 2,4-dinitrobenzenesulfonyl groups are excised to recover secondary amino groups, whose p Ka is proved to be 7.21. As a consequence, the molecular weight loss of the hydrophobic segment and the protonation of amino groups induce significant disturbance of hydrophilic/hydrophobic balance, leading to the disassembly of the nanoprobes and regain of spin-spin relaxation and 19F NMR/MRI signals ("ON" state, T2 up to 296 ± 5.3 ms). This nanoprobe shows high sensitivity and selectivity to biothiol...Continue Reading

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Citations

Jan 4, 2019·Nanoscale·Xiangjun HanKhashayar Farsad
May 30, 2020·Chemistry : a European Journal·Nicholas G TaylorFrank A Leibfarth
Oct 17, 2020·International Journal of Nanomedicine·Lina WuXilin Sun
Mar 10, 2021·Chemical Society Reviews·Jia Lv, Yiyun Cheng
Mar 11, 2019·ACS Biomaterials Science & Engineering·Yumin ZhangJianfeng Liu
Sep 20, 2019·Bioconjugate Chemistry·Mi Hyeon ChoYongdoo Choi
Aug 7, 2018·Chemical Reviews·Zhenchuang XuYanchuan Zhao

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