Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 23, Pages 6440-6444Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201700426
Keywords
F-19 NMR spectroscopy; fluorination; magnetic resonance imaging; molecular imaging; peptides
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Funding
- University of Minnesota
- Research Corporation Cottrell Scholar Award
- Heisig-Gleysteen Fellowship
- University of Minnesota Undergraduate Research Scholarship (URS)
- Minnesota Lions Diabetes Foundation
- Schott Family Foundation
- Carol Olson Memorial Diabetes Research Fund
- NIH [P41 EB015894, S10 RR025031]
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F-19 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 F-19 signal. Here, we describe a new class of high-signal, water-soluble fluorochemicals as F-19 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-epsilon-trifluoroacetyllysine and lysine provide a degenerate F-19 NMR signal. F-19 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.
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