Abstract
Syntheses of N-3(substituted) analogues of thymidine, N-3([ 18F]fluorobutyl)thymidine ([18F]-FBT) and N-3([ 18F]fluoropentyl)thymidine ([18F]-FPT) are reported. 1,4-Butane diol and 1,5 pentane diol were converted to their tosyl derivatives 2 and 3 followed by conversion to benzoate esters 4 and 5, respectively. Protected thymidine 1 was coupled separately with 4 and 5 to produce 6 and 7, which were hydrolyzed to 8 and 9, then converted to their mesylates 10 and 11, respectively. Compounds 10 and 11 were fluorinated with n-Bu4N[ 18F] to produce 12 and 13, which by acid hydrolysis yielded 14 and 15, respectively. The crude products were purified by HPLC to obtain [ 18F]-FBT and [18F]-FPT. The radiochemical yields were 58-65% decay corrected (d.c.) for 14 and 46-57% (d.c.) for 15 with an average of 56% in three runs per compound. Radiochemical purity was > 99% and specific activity was > 74 GBq/μmol at the end of synthesis (EOS). The synthesis time was 65-75 min from the end of bombardment (EOB).
Original language | English (US) |
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Pages (from-to) | 1079-1088 |
Number of pages | 10 |
Journal | Journal of Labelled Compounds and Radiopharmaceuticals |
Volume | 49 |
Issue number | 12 |
DOIs | |
State | Published - Oct 30 2006 |
Keywords
- Fluorine-18
- PET
- TK1
- Thymidine
ASJC Scopus subject areas
- Analytical Chemistry
- Biochemistry
- Radiology Nuclear Medicine and imaging
- Drug Discovery
- Spectroscopy
- Organic Chemistry