PUBLICATION
Highly Fluorinated Peptide Probes with Enhanced In Vivo Stability for 19 F-MRI
- Authors
- Meng, B., Grage, S.L., Babii, O., Takamiya, M., MacKinnon, N., Schober, T., Hutskalov, I., Nassar, O., Afonin, S., Koniev, S., Komarov, I.V., Korvink, J.G., Strähle, U., Ulrich, A.S.
- ID
- ZDB-PUB-220909-7
- Date
- 2022
- Source
- Small (Weinheim an der Bergstrasse, Germany) 18(41): e2107308 (Journal)
- Registered Authors
- Strähle, Uwe, Takamiya, Masanari
- Keywords
- 19F-MRI, bioconjugation, fluorescence imaging, highly fluorinated peptides, perfluoro-tert-butyl amino acid, zebrafish embryos
- MeSH Terms
-
- Alkynes
- Amides
- Amino Acids/chemistry
- Animals
- Asparagine*
- Magnetic Resonance Imaging
- Peptides/chemistry
- Serum Albumin, Bovine*
- Zebrafish
- beta-Alanine
- PubMed
- 36074982 Full text @ Small
Citation
Meng, B., Grage, S.L., Babii, O., Takamiya, M., MacKinnon, N., Schober, T., Hutskalov, I., Nassar, O., Afonin, S., Koniev, S., Komarov, I.V., Korvink, J.G., Strähle, U., Ulrich, A.S. (2022) Highly Fluorinated Peptide Probes with Enhanced In Vivo Stability for 19 F-MRI. Small (Weinheim an der Bergstrasse, Germany). 18(41):e2107308.
Abstract
A labeling strategy for in vivo 19 F-MRI (magnetic resonance imaging) based on highly fluorinated, short hydrophilic peptide probes, is developed. As dual-purpose probes, they are functionalized further by a fluorophore and an alkyne moiety for bioconjugation. High fluorination is achieved by three perfluoro-tert-butyl groups, introduced into asparagine analogues by chemically stable amide bond linkages. d-amino acids and β-alanine in the sequences endow the peptide probes with low cytotoxicity and high serum stability. This design also yielded unstructured peptides, rendering all 27 19 F substitutions chemically equivalent, giving rise to a single 19 F-NMR resonance with <10 Hz linewidth. The resulting performance in 19 F-MRI is demonstrated for six different peptide probes. Using fluorescence microscopy, these probes are found to exhibit high stability and long circulation times in living zebrafish embryos. Furthermore, the probes can be conjugated to bovine serum albumin with only amoderate increase in 19 F-NMR linewidth to ≈30 Hz. Overall, these peptide probes are hence suitable for in vivo 19 F-MRI applications.
Genes / Markers
Expression
Phenotype
Mutations / Transgenics
Human Disease / Model
Sequence Targeting Reagents
Fish
Orthology
Engineered Foreign Genes
Mapping