Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

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

Synthesis of Intrinsically Disordered Fluorinated Peptides for Modular Design of High-Signal 19F MRI Agents
Bradley P. Weegman, Sofia D. Maltseva, Michael Garwood, Steven E. Kirberger, Joseph C. Manulik, William C. K. Pomerantz, Samuel A. Einstein
19F 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 19F signal. Here, we describe a new class of high-signal, water-soluble fluorochemicals as 19F 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 19F NMR signal. 19F 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. Disordered symmetry: A new class of water-soluble, peptide-based fluorochemicals as high-signal 19F MRI imaging agents is described. The design strategy utilizes an alternating sequence of positive charges and fluorinated amino acids to produce a disordered peptide with overlapping 19F resonances yielding a singular intense signal for use as a 19F MRI agent.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201700426

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