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

Steven E. Kirberger, Sofia D. Maltseva, Joseph C. Manulik, Samuel A. Einstein, Bradley P. Weegman, Michael Garwood, William C.K. Pomerantz

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)6440-6444
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number23
DOIs
StatePublished - Jan 1 2017

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Magnetic resonance imaging
Peptides
Molecular imaging
Imaging techniques
Fluorine
Nylons
Biological systems
Polyamides
Lysine
Tuning
Nuclear magnetic resonance
Proteins
Water

Keywords

  • F NMR spectroscopy
  • fluorination
  • magnetic resonance imaging
  • molecular imaging
  • peptides

Cite this

Synthesis of Intrinsically Disordered Fluorinated Peptides for Modular Design of High-Signal 19 F MRI Agents. / Kirberger, Steven E.; Maltseva, Sofia D.; Manulik, Joseph C.; Einstein, Samuel A.; Weegman, Bradley P.; Garwood, Michael; Pomerantz, William C.K.

In: Angewandte Chemie - International Edition, Vol. 56, No. 23, 01.01.2017, p. 6440-6444.

Research output: Contribution to journalArticle

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