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Synthesis of [ 18 F]‐labeled adenosine analogues as potential PET imaging agents
Author(s) -
Alauddin Mian M.,
Fissekis John D.,
Conti Peter S.
Publication year - 2003
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.712
Subject(s) - chemistry , trifluoromethanesulfonate , hydrolysis , adenosine , high performance liquid chromatography , specific activity , radiochemistry , fluoride , chromatography , nuclear chemistry , organic chemistry , catalysis , inorganic chemistry , biochemistry , enzyme
The syntheses of adenosine analogues, 2′‐deoxy‐2′‐[ 18 F]fluoro‐9‐β‐ D ‐arabinofuranosyladenine ([ 18 F]‐FAA) and 3′‐deoxy‐3′‐[ 18 F]fluoro‐9‐β‐ D ‐xylofuranosyladenine ([ 18 F]‐FXA) are reported. Adenosine ( 1 ) was converted to its methoxytrityl derivatives 2 and 3 as a mixture. After separation, these derivatives were converted to their respective triflates 4 and 5 . Each triflate was reacted with tetrabutylammonium[ 18 F]fluoride to produce 6b or 7b , which by acidic hydrolysis yielded compounds 8b and 9b . Crude preparations were purified by HPLC to obtain the desired pure products. The radiochemical yields were 10‐18% decay corrected (d. c.) for 8b and 30‐40% (d. c.) for 9b in 4 and 3 runs, respectively. Radiochemical purity was >99% and specific activity was >74 GBq/μmol at the end of synthesis (EOS). The synthesis time was 90‐95 min from the end of bombardment (EOB). Copyright © 2003 John Wiley & Sons, Ltd.