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

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2017 May 5

PMID 28471097

Citations 15

Authors

Steven E Kirberger

Sofia D Maltseva

Joseph C Manulik

Samuel A Einstein

Bradley P Weegman

Michael Garwood

William C K Pomerantz

Affiliations

Soon will be listed here.

Abstract

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 F signal. Here, we describe a new class of high-signal, water-soluble fluorochemicals as 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 F NMR signal. 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.

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