Automated radiosynthesis of the thiol-reactive labeling agent N-[6-(4-[18F]fluorobenzylidene)aminooxyhexyl]maleimide ([18F]FBAM).

The two-step radiosynthesis of N-[6-(4-[(18)F]fluorobenzylidene)aminooxyhexyl]maleimide ([(18)F]FBAM) was adapted to a remotely controlled synthesizer module. After optimization of reaction conditions as well as solid phase extraction based purification steps, the final [(18)F]FBAM was obtained in a decay-corrected radiochemical yield of 29±4% (related to [(18)F]fluoride, n=12) within a total synthesis time of 40 min. The radiochemical purity of [(18)F]FBAM was in the range 94-98%, the specific activity was determined with 13.4-17.2 GBq/μmol.

Kniess T ，Kuchar M ，Pietzsch J 《-》

1-[3-(2-[18F]fluoropyridin-3-yloxy)propyl]pyrrole-2,5-dione: design, synthesis, and radiosynthesis of a new [18F]fluoropyridine-based maleimide reagent for the labeling of peptides and proteins.

de Bruin B ，Kuhnast B ，Hinnen F ，Yaouancq L ，Amessou M ，Johannes L ，Samson A ，Boisgard R ，Tavitian B ，Dollé F ... -  《BIOCONJUGATE CHEMISTRY》

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).

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.

Kapty J ，Kniess T ，Wuest F ，Mercer JR ... -  《-》

Labeling of low-density lipoproteins using the 18F-labeled thiol-reactive reagent N-[6-(4-[18F]fluorobenzylidene)aminooxyhexyl]maleimide.

Berndt M ，Pietzsch J ，Wuest F 《-》

Module-assisted synthesis of the bifunctional labelling agent N-succinimidyl 4-[(18)F]fluorobenzoate ([(18)F]SFB).

Mäding P ，Füchtner F ，Wüst F 《APPLIED RADIATION AND ISOTOPES》