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[ N ‐methyl‐ 11 C]MeAIB, a tracer for system A amino acid transport: preparation from [ 11 C]methyl triflate and HPLC metabolite analysis of plasma samples after intravenous administration in man
Author(s) -
Någren Kjell,
Sutinen Eija,
Jyrkkiö Sirkku
Publication year - 2000
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 - 10.1002/1099-1344(200009)43:10<1013::aid-jlcr387>3.0.co;2-h
Subject(s) - chemistry , high performance liquid chromatography , trifluoromethanesulfonate , metabolite , hydrolysis , chromatography , amino acid , yield (engineering) , organic chemistry , biochemistry , catalysis , materials science , metallurgy
MeAIB, α‐methylamino‐isobutyric acid, is an achiral synthetic amino acid which is a highly selective substrate for the A‐type, or alanine‐preferring, amino acid transport system. [ N ‐methyl‐ 11 C]MeAIB ([ 11 C]MeAIB) was prepared by reaction of [ 11 C]methyl triflate with AIB methyl ester, generated in situ from its corresponding hydrochloride, followed by hydrolysis of the ester function with aqueous NaOH. After HPLC‐purification, the product was obtained in a 60–70% decay corrected yield counted from [ 11 C]methyl triflate. The total synthesis time was 32–37 min and the radiochemical purity of the product higher than 98%. HPLC analysis of plasma samples taken 5–30 min after the administration of [ 11 C]MeAIB to man showed that more than 95% of the total radioactivity in the plasma consisted of unchanged [ 11 C]MeAIB. The simple preparation and the high metabolic stability of [ 11 C]MeAIB makes this novel tracer a potential candidate for positron emission tomography investigations for the system A amino acid transport system in vivo . Copyright © 2000 John Wiley & Sons, Ltd.