Radiolabeling of phosphatidylserine-binding peptides with prosthetic groups N-[6-(4-[18F]fluorobenzylidene)aminooxyhexyl]maleimide ([18F]FBAM) and N-succinimidyl-4-[18F]fluorobenzoate ([18F]SFB).

Janice Kapty, Torsten Kniess, Frank Wuest, John R Mercer

Department of Oncology, Faculty of Medicine and Dentistry, University of Alberta, Edmonton, Canada. jkapty@ualberta.ca

Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 2011 Sep

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The widely used (18)F-prosthetic group N-succinimidyl-4-[(18)F]fluorobenzoate ([(18)F]SFB) and the recently developed N-[6-(4-[(18)F]fluorobenzylidene)aminooxyhexyl]maleimide ([(18)F]FBAM) were investigated for radiolabeling of two representative phosphatidylserine-binding peptides. The prosthetic groups were compared with respect to required reactions conditions for optimum labeling, radiolabeling yield and chemoselectivity. The N-terminus labeled product produced by reaction of [(18)F]SFB with binding peptide LIKKPF was produced in 18% radiochemical yield while no N-terminus labeled product could be isolated following [(18)F]SFB reaction with PDGLSR. When the peptides were modified by addition of a cysteine residue at the N-terminus they provided almost quantitative radiochemical yields with [(18)F]FBAM. Results indicate that for the peptides in this study, [(18)F]FBAM is a more useful prosthetic group compared to [(18)F]SFB due to its excellent chemoselectivity and high radiochemical yield. Copyright © 2011 Elsevier Ltd. All rights reserved.

Citation

Janice Kapty, Torsten Kniess, Frank Wuest, John R Mercer. Radiolabeling of phosphatidylserine-binding peptides with prosthetic groups N-[6-(4-[18F]fluorobenzylidene)aminooxyhexyl]maleimide ([18F]FBAM) and N-succinimidyl-4-[18F]fluorobenzoate ([18F]SFB). Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine. 2011 Sep;69(9):1218-25