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Rapid synthesis of maleimide functionalized fluorine‐18 labeled prosthetic group using “radio‐fluorination on the Sep‐Pak” method
Author(s) -
Basuli Falguni,
Zhang Xiang,
Jagoda Elaine M.,
Choyke Peter L.,
Swenson Rolf E.
Publication year - 2018
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3623
Subject(s) - chemistry , maleimide , fluorine , trifluoromethanesulfonate , yield (engineering) , pyrrole , acetonitrile , halogenation , salt (chemistry) , chemical synthesis , ammonium , nuclear chemistry , organic chemistry , catalysis , biochemistry , materials science , metallurgy , in vitro
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‐HCO 3 ). 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.