Journal
ACS APPLIED MATERIALS & INTERFACES
Volume 10, Issue 22, Pages 18532-18542Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsami.8b03764
Keywords
F-19-MRI; nanoprobe; reducing microenvironment; amino activation; thiol imaging
Funding
- National Natural Science Foundation of China [31670977, 51203189, 51703246, 81220108015]
- Tianjin Natural Science Foundation [16JCQNJC14200, 17JCQNJC13800]
- Science and Technology Support Program of Tianjin [15RCGFSY00146]
- CAMS Innovation Fund for Medical Sciences (CIFMS) [2016-I2M-3-022]
- Natural Science Foundation key project [31630027, 31430031]
- National Distinguished Young Scholars grant [31225009]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDA09030301]
- external cooperation program of BIC, Chinese Academy of Science [121D11KYSB20130006]
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F-19-magnetic resonance imaging (MRI) is of great significance for noninvasive imaging and detection of various diseases. However, the main obstacle in the application of F-19-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 F-19-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 F-19-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 pK(a) 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 F-19-NMR/MRI signals (ON state, T-2 up to 296 +/- 5.3 ms). This nanoprobe shows high sensitivity and selectivity to biothiols, enabling intracellular and intratumoral imaging of glutathione. Our study not only provides a new nanoprobe candidate for biothiols imaging in vivo but also a promising strategy for the molecular design of real watersoluble and highly sensitive F-19-MRI nanoprobes.
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