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J Nucl Med. 2008; 49 (Supplement 1):96P
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Radiopharmaceutical Chemistry: New Chemistry-Oncology

New Chemistry-Oncology I: Peptides

‘Click labeling’ of an RGD peptide using 2-[18F]fluoroethylazide – Comparison with 18F-fluorothiol and 18F-fluoroaldehyde coupling

Matthias Glaser1, Magne Solbakken2, Joseph Arukwe2, Hege Karlsen2, Alan Cuthbertson2, Sajinder Luthra1 and Erik Arstad1

1 Hammersmith Imanet Ltd, GE Healthcare, London, United Kingdom; 2 MDx Research, GE Healthcare, Oslo, Norway

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Objectives: The aim of this study was to identify radiochemical methods that enable a reliable, large-scale automated production of 18F-labeled RGD peptides.

Methods: Using a peptide backbone based on an established RGD SPECT marker, we herein compare the potential of three labeling methods with regard to routine production using 18F-fluoroalkylthiols, 18F-fluoroaldehydes, and 2-[18F]fluoroethylazide.

Results: Attempted coupling of 3-[18F]fluoropropane-1-thiol to the chloroacetamide peptide precursor proceeded in poor yield. In contrast, 18F-fluoroaldehydes reacted readily with the aminooxy modified peptide (isolated r.c.y. 16-26%, decay-corrected). This method was particularly attractive, as formation of the labeling agent and subsequent bioconjugation could be achieved using a simple one-pot procedure. Here, 4-[18F]fluorobenzaldehyde provided the best r.c.y. (23±5%, n=3). The ‘Click labeling’ step of the alkyne containing RGD peptide with 2-[18F]fluoroethylazide afforded the labeled peptide in a r.c.y. of 70±5% (n=3) for solution phase (Na-ascorbate/CuSO4) and 42±14 % (n =5) for solid phase (Cu powder) catalysis, respectively.

Conclusions: Labeling based on 4-[18F]fluorobenzaldehyde/aminooxy conjugation was found to be the superior for the automated production of the 18F-RGD peptide. While the results using the new labeling reagent 2-[18F]fluoroethylazide provided higher yields for the conjugation step, the need for distillation of 2-[18F]fluoroethylazide is still a limiting factor for the automation of this method.





This Article
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Right arrow Alert me to new issues of the journal
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Right arrow Articles by Glaser, M.
Right arrow Articles by Arstad, E.
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Right arrow Articles by Glaser, M.
Right arrow Articles by Arstad, E.