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Rapid Synthesis of Maleimide Functionalized fluorine-18 Labeled Prosthetic Group Using "Radio-Fluorination on the Sep-Pak" Method

Rapid Synthesis of Maleimide Functionalized fluorine-18 Labeled Prosthetic Group Using "Radio-Fluorination on the Sep-Pak" Method

Falguni Basuli, Xiang Zhang, Elaine M Jagoda, Peter L Choyke, Rolf E Swenson

J Labelled Comp Radiopharm. 2018 Jun 30;61(8):599-605.

PMID: 29575176

Abstract:

Following our recently published fluorine-18 labeling method, "Radio-fluorination on the Sep-Pak", we have successfully synthesized 6-[18 F]fluoronicotinaldehyde by passing a solution (1:4 acetonitrile: t-butanol) of its quaternary ammonium salt precursor, 6-(N,N,N-trimethylamino)nicotinaldehyde trifluoromethanesulfonate (2), through a fluorine-18 containing anion exchange cartridge (PS-HCO3 ). Over 80% radiochemical conversion was observed using 10 mg of precursor within 1 minute. The [18 F]fluoronicotinaldehyde ([18 F]5) was then conjugated with 1-(6-(aminooxy)hexyl)-1H-pyrrole-2,5-dione to prepare the fluorine-18 labeled maleimide functionalized prosthetic group, 6-[18 F]fluoronicotinaldehyde O-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexyl) oxime, 6-[18 F]FPyMHO ([18 F]6). The current Sep-Pak method not only improves the overall radiochemical yield (50 ± 9%, decay-corrected, n = 9) but also significantly reduces the synthesis time (from 60-90 minutes to 30 minutes) when compared with literature methods for the synthesis of similar prosthetic groups.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP38542948	Ammonium trifluoromethanesulfonate		38542-94-8	Price

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