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Synthesis of N‐tert ‐butyl‐α‐(4‐[ 18 F]fluorophenyl)‐nitrone ([ 18 F]FPBN) for in vivo detection of free radicals
Author(s) -
Bormans G.,
Kilbourn M. R.
Publication year - 1995
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.2580360202
Subject(s) - nitrone , chemistry , radical , nucleophilic substitution , yield (engineering) , medicinal chemistry , hydroxylamine , trifluoromethanesulfonate , electron paramagnetic resonance , fluoride , nuclear chemistry , organic chemistry , inorganic chemistry , cycloaddition , materials science , physics , nuclear magnetic resonance , metallurgy , catalysis
We have synthesized the fluorine‐18 labeled derivative of N ‐ tert ‐butyl‐α‐phenylnitrone (PBN), a free radical spin trapping agent widely used with electron spin resonance (ESR). N ‐ tert ‐Butyl‐α‐(4‐[ 18 F]fluorophenyl)‐nitrone ([ 18 F]FPBN) could be prepared with low radiochemical yield (3% decay corrected) by the direct aromatic nucleophilic substitution of N ‐ tert ‐butyl‐α‐(4‐nitrophenyl)nitrone with [ 18 F]fluoride. An alternate two step synthesis route consisted of the nucleophilic [ 18 F]fluoride substitution of 4‐ N , N , N ‐trimethylammoniumbenzaldehyde triflate to yield 4‐[ 18 F]fluorobenzaldehyde, which was distilled into a vial containing N ‐ tert ‐butyl‐hydroxylamine in 2N NaOH. 4‐[ 18 F]Fluorobenzaldehyde readily reacted with the hydroxylamine to form [ 18 F]FPBN. [ 18 F]FPBN was obtained in overall decay corrected yields of 24% in a total synthesis time < 45 min. and was suitable for further applications in in vivo studies of free radicals.