Abstract
Three strategies for chemoselective labeling of RGD peptides with 18F have been compared. Aminooxy [18F]fluorobenzaldehyde conjugation provided 40 ± 12% decay-corrected radiochemical yield using a fully automated method. An one-pot protocol for ‘click labeling’ of the RGD scaffold with 2-[18F]fluoroethylazide afforded 47 ± 8% decay-corrected radiochemical yield. Attempted conjugation with 3-[18F]fluoropropanethiol led to extensive decomposition and was therefore found unsuitable for labeling of the RGD peptide investigated. The results suggest that ‘click labeling’ of RGD peptides provides an attractive alternative to aminooxy aldehyde condensation, however, 2-[18F]-fluoroethylazide may be too small to allow separation of large 18F-labeled RGD peptides from their precursors.
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Acknowledgments
We thank Bruce Mackay, Colin Steel, and the Cyclotron Team at Hammersmith Imanet for producing fluorine-18. We are also grateful to Sue Champion, GE Healthcare MDX Research, for providing 4-N,N,N-trimethylanilium aldehyde trifluoromethanesulfonate.
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Glaser, M., Solbakken, M., Turton, D.R. et al. Methods for 18F-labeling of RGD peptides: comparison of aminooxy [18F]fluorobenzaldehyde condensation with ‘click labeling’ using 2-[18F]fluoroethylazide, and S-alkylation with [18F]fluoropropanethiol. Amino Acids 37, 717–724 (2009). https://doi.org/10.1007/s00726-008-0200-0
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DOI: https://doi.org/10.1007/s00726-008-0200-0