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Amino Acids

, Volume 43, Issue 4, pp 1431–1443 | Cite as

Site-selective radiolabeling of peptides by 18F-fluorobenzoylation with [18F]SFB in solution and on solid phase: a comparative study

  • Manuela Kuchar
  • Marc Pretze
  • Torsten Kniess
  • Jörg Steinbach
  • Jens Pietzsch
  • Reik LöserEmail author
Original Article

Abstract

Peptides labeled with short-lived positron-emitting radionuclides are of outstanding interest as probes for molecular imaging by positron emission tomography (PET). Herein, the site-selective incorporation of fluorine-18 into lysine-containing peptides using the prosthetic labeling agent N-succinimidyl 4-[18F]fluorobenzoate ([18F]SFB) is described. The reaction of [18F]SFB with four biologically relevant resin-bound peptides was studied and optimized. For comparison, each peptide was 18F-fluorobenzoylated in solution under different conditions and the product distribution was analyzed confirming the advantages of the solid-phase approach. The method’s feasibility for selective radiolabeling either at the N-terminus or at the lysine side chain was demonstrated. Labeling on solid phase with [18F]SFB resulted in crude 18F-fluorobenzoylpeptides whose radiochemical purities were typically greater than 90% and that could be prepared in synthesis times from 65 to 76 min.

Keywords

Fluorine-18 Solid-phase synthesis Regioselectivity Positron emission tomography 

Notes

Acknowledgments

The dedicated assistance of Uta Lenkeit and Peggy Wecke in the radiosynthesis of [18F]SFB is gratefully acknowledged.

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

726_2012_1216_MOESM1_ESM.pdf (485 kb)
Supplementary material 1 (PDF 485 kb)

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Copyright information

© Springer-Verlag 2012

Authors and Affiliations

  • Manuela Kuchar
    • 1
  • Marc Pretze
    • 1
  • Torsten Kniess
    • 1
  • Jörg Steinbach
    • 1
  • Jens Pietzsch
    • 1
  • Reik Löser
    • 1
    Email author
  1. 1.Institut für Radiopharmazie, Helmholtz-Zentrum Dresden-RossendorfDresdenGermany

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