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Synthesis of 3′‐deoxy‐3′‐[ 18 F]fluoro‐thymidine with 2,3′‐anhydro‐5′‐ O ‐(4,4′‐dimethoxytrityl)‐thymidine
Author(s) -
Wodarski C.,
Eisenbarth J.,
Weber K.,
Henze M.,
Haberkorn U.,
Eisenhut M.
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(20001030)43:12<1211::aid-jlcr408>3.0.co;2-#
Subject(s) - chemistry , thymidine , radiochemistry , stereochemistry , dna , biochemistry
[ 11 C]Thymidine has been used as a proliferation marker in positron‐emission‐tomography (PET) studies of tumors. This compound showed metabolite related problems and the radiosynthesis proved to be difficult. Recently, the more stable 3′‐deoxy‐3′‐[ 18 F]fluorothymidine ([ 18 F]FLT) has been suggested as an alternative. One advantage of [ 18 F]FLT is based on thymidine kinase‐1 catalyzed phosphorylation of FLT and the intracellular accumulation of this metabolite without participation in DNA synthesis. The radiosynthesis of [ 18 F]FLT originally designed by Grierson et al. was found to be demanding especially regarding the workup of the [ 18 F]fluoride/1‐(2‐deoxy‐3‐ O ‐nosyl‐5‐ O ‐DMT‐β‐D‐ threo ‐pento‐furanosyl)‐3‐DMBn‐thymine reaction mixture. Instead, we used 2,3′‐anhydro‐5′‐ O ‐(4,4′‐dimethoxytrityl)thymidine as a precursor for the synthesis of [ 18 F]FLT. In DMSO at 175°C and in presence of Kryptofix ® 2.2.2. we obtained 5.6± 1,4% [ 18 F]FLT (EOS). Copyright © 2000 John Wiley & Sons, Ltd.