4-[18F]Fluorobenzaldehyde-O-(2-{2-[2-(pyrol-2,5-dion-1-yl)ethoxy] ethoxy}ethyl)oxim ([18F]FBOM): A novel prosthetic group for mild labelling of SH-group bearing biomacromolecules


4-[18F]Fluorobenzaldehyde-O-(2-{2-[2-(pyrol-2,5-dion-1-yl)ethoxy] ethoxy}ethyl)oxim ([18F]FBOM): A novel prosthetic group for mild labelling of SH-group bearing biomacromolecules

Vogler, L.; Berndt, M.; Pietzsch, J.; Hultsch, C.; Wüst, F.

The synthesis and application of 4-[18F]fluorobenzaldehyde-O-(2-{2-[2-(pyrol-2,5-dion-1-yl)ethoxy]ethoxy}ethyl)oxim ([18F]FBOM) as a novel prosthetic group for 18F labelling of SH-group bearing biomacromolecules is described.
The aminooxy-functionalised labelling precursor for the radiosynthesis of [18F]FBOM was synthesised in a four-step synthesis sequence with a total yield of 14%. [18F]FBOM could be obtained in a condensation reaction between the labelling precursor and [18F]fluorobenzaldehyde through formation of an oxim. The radiochemical yield ranged between 14 and 19% (decay-corrected). In a typical experiment, starting from 6.5 GBq of [18F]fluoride 730MBq of [18F]FBOM could be obtained within 80 minutes (including HPLC purification). The specific activity was determined to be 51 GBq/µmol. The lipophilicity of [18F]FBOM was determined to be logP = 0.84. The use of [18F]FBOM as SH-reactive group prosthetic group was demonstrated by the reaction with glutathion, low densitiy lipoproteins (LDL) and modified neurotensin derivatives. [18F]FBOM can easily be synthesised, and [18F]FBOM represents an interesting novel prosthetic group for the labelling of SH-group containing biomacromolecules with 18F under mild conditions.

  • Lecture (others)
    14. Arbeitsgruppentagung Radiochemie/Radiopharmazie, 04.-05.10.2006, Marburg, Germany

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Publ.-Id: 10107