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

Berndt, M.; Pietzsch, J.; Wüst, F.
The novel thiol group-selective bifunctional 18F-labeling agent N-[6-(4-[18F]fluoro-benzylidene)aminooxyhexyl]maleimide ([18F]FBAM) has been developed. The bifunctional labeling precursor 4 containing a thiol-reactive maleimide group and a carbonyl group-reactive aminooxy group was prepared in only three steps in a total chemical yield of 59%.
Subsequent radiolabeling with 4-[18F]fluorobenzaldehyde gave the bifunctional 18F-labeling agent [18F]FBAM in 29% radiochemical yield. In a typical experiment 3.88 GBq of [18F]fluoride could be converted into 723 MBq of [18F]FBAM within 69 min. Conjugation of [18F]FBAM with thiol groups was exemplified with the cystein-containing tripeptide glutathione and with various apolipoproteins of human low density lipoproteins (LDL) subfractions. The latter one was evaluated with respect to uptake of [18F]FBAM-LDL subfractions in human hepatoma cells (HepG2) in vitro. In vivo biodistribution studies in rats revealed high stability for the [18F]FBAM-LDL subfractions. Moreover, the metabolic fate of the [18F]FBAM-LDL subfractions in vivo was delineated by dynamic PET studies using a dedicated small animal tomograph. Data were compared to former studies using the NH2-reactive 18F-labeling agent N-succinimidyl-4-[18F]fluorobenzoate ([18F]SFB). Compound [18F]FBAM can be considered to be an excellent prosthetic group for the selective and mild 18F-labeling of thiol group-containing biomolecules suitable for subsequent investigations in vitro and in vivo.

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Permalink: https://www.hzdr.de/publications/Publ-8975
Publ.-Id: 8975