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Synthesis of [ 18 F]‐6‐deoxy‐6‐fluoro‐ D ‐glucose ([ 18 F]6FDG), a potential tracer of glucose transport
Author(s) -
Neal Timothy R.,
Schumann William C.,
Berridge Marc S.,
Landau Bernard R.
Publication year - 2005
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.1003
Subject(s) - chemistry , yield (engineering) , hydrolysis , d glucose , tracer , in vivo , radioligand , glucose transporter , radiochemistry , fluoride , specific activity , nuclear chemistry , stereochemistry , in vitro , organic chemistry , biochemistry , inorganic chemistry , endocrinology , insulin , enzyme , medicine , materials science , physics , microbiology and biotechnology , nuclear physics , metallurgy , biology
Abstract With the goal of developing a PET radioligand for the in vivo assessment of glucose transport, 6‐deoxy‐6‐[ 18 F]fluoro‐ D ‐glucose ([ 18 F]6FDG) was prepared in two steps from 18 F − . Starting with D ‐glucose, the tosyl‐ and mesyl‐derivatives of 3,5‐ O ‐benzylidene‐1,2‐ O ‐isopropylidene‐ α ‐ D ‐glucofuranose were prepared by known methods. Reaction of either of these precursors with 18 F − resulted in the formation of 3,5‐ O ‐benzylidene‐6‐deoxy‐6‐[ 18 F]‐fluoro‐1,2‐ O ‐isopropylidene‐ α ‐ D ‐glucofuranose in high yield. Subsequent hydrolysis resulted in the production of [ 18 F]6FDG. Under optimal conditions, [ 18 F]6FDG is produced 60–70 min after end of bombardment (EOB) in 71 ± 12% yield (decay corrected, based upon fluoride) with a radiochemical purity of ⩾96%. Preliminary experiments have indicated that [ 18 F]6FDG may be a more representative in vivo tracer for the glucose transporter than 2FDG. Copyright © 2005 John Wiley & Sons, Ltd.