Synthesis of Intrinsically Disordered Fluorinated Peptides for Modular Design of High‐Signal 19 F MRI Agents

19 F MRI is valuable for in vivo imaging due to the only trace amounts of fluorine in biological systems. Because of the low sensitivity of MRI however, designing new fluorochemicals remains a significant challenge for achieving sufficient 19 F signal. Here, we describe a new class of high‐signal, w...

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Bibliographic Details
Published in:Angewandte Chemie 2017-06, Vol.129 (23), p.6540-6544
Main Authors: Kirberger, Steven E., Maltseva, Sofia D., Manulik, Joseph C., Einstein, Samuel A., Weegman, Bradley P., Garwood, Michael, Pomerantz, William C. K.
Format: Article
Language:English
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Summary:19 F MRI is valuable for in vivo imaging due to the only trace amounts of fluorine in biological systems. Because of the low sensitivity of MRI however, designing new fluorochemicals remains a significant challenge for achieving sufficient 19 F signal. Here, we describe a new class of high‐signal, water‐soluble fluorochemicals as 19 F MRI imaging agents. A polyamide backbone is used for tuning the proteolytic stability to avoid retention within the body, which is a limitation of current state‐of‐the‐art perfluorochemicals. We show that unstructured peptides containing alternating N‐ϵ‐trifluoroacetyllysine and lysine provide a degenerate 19 F NMR signal. 19 F MRI phantom images provide sufficient contrast at micromolar concentrations, showing promise for eventual clinical applications. Finally, the degenerate high signal characteristics were retained when conjugated to a large protein, indicating potential for in vivo targeting applications, including molecular imaging and cell tracking.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201700426