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N 3 ‐Substituted thymidine analogues III: radiosynthesis of N 3 ‐[(4‐[ 18 F]fluoromethyl‐phenyl)butyl]thymidine ([ 18 F]‐FMPBT) and N 3 ‐[(4‐[ 18 F]fluoromethyl‐phenyl)pentyl] thymidine ([ 18 F]‐FMPPT) for PET
Author(s) -
Ghosh Pradip,
Gelovani Juri G.,
Alauddin Mian M.
Publication year - 2007
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.1425
Subject(s) - chemistry , thymidine , radiosynthesis , hydrolysis , yield (engineering) , stereochemistry , radiochemistry , carbon 14 , medicinal chemistry , nuclear chemistry , organic chemistry , dna , in vivo , biochemistry , materials science , microbiology and biotechnology , metallurgy , biology , physics , quantum mechanics
Abstract Radiosyntheses of two N 3 ‐substituted thymidine analogues, N 3 ‐[(4[ 18 F]fluoromethyl‐phenyl)butyl]thymidine ([ 18 F]‐FMPBT) and N 3 ‐[(4[ 18 F]fluoromethyl‐phenyl)pentyl]thymidine ([ 18 F]‐FMPPT), are reported. The precursor compounds 9 and 10 were synthesized in six steps and the standard compounds 13 and 14 were synthesized from these precursors. For radiosynthesis, compounds 9 and 10 were fluorinated with n ‐Bu 4 N[ 18 F] to produce [ 18 F]‐ 11 and [ 18 F]‐ 12 , which by acid hydrolysis yielded [ 18 F]‐ 13 and [ 18 F]‐ 14 , respectively. The crude products were purified by high‐performance liquid chromatography to obtain [ 18 F]‐FMPBT and [ 18 F]‐FMPPT. The average decay‐corrected radiochemical yield for [ 18 F]‐ 13 was 15% in five runs, and that for [ 18 F]‐ 14 was 10% in four runs. The radiochemical purity was >99% and the specific activity was >74 GBq/µmol at the end of synthesis. The synthesis time was 80–90 min from the end of bombardment. Copyright © 2007 John Wiley & Sons, Ltd.