High radiochemical yield synthesis of 3'-deoxy-3'-[18F]fluorothymidine using (5'-O-dimethoxytrityl-2'-deoxy-3'-O-nosyl-beta-D-threo pentofuranosyl)thymine and its 3-N-BOC-protected analogue as a labeling precursor.
We prepared 3'-deoxy-3'-[(18)F]fluorothymidine ([(18)F]FLT) from 3'-O-nosyl thymidine derivative 3 or its pyrimidine ring N-BOC-protected analogue 5 and optimized [(18)F]fluorination condition for a high radiochemical yield. The optimal condition for [(18)F]fluorination with precursor 3 was 30 mg (41.1 micromol)/300 microl CH(3)CN at 130 degrees C for 5 min, while precursor 5 required 34 mg (40 micromol)/300 microl CH(3)CN at 110 degrees C for 5 min. After HPLC purification at neutral pH, we achieved high radiochemical yields of 40 +/- 5.2% and 42 +/- 5.4% (decay-corrected) within 60 min of preparation time with radiochemical purities of >97%.
Yun
Mikyung
M
Department of Nuclear Medicine, Asan Medical Center, University of Ulsan College of Medicine, 388-1 Pungnap-dong, Songpa-gu, Seoul 138-736, South Korea.
Oh
Seung Jun
SJ
Ha
Hyun-Joon
HJ
Ryu
Jin Sook
JS
Moon
Dae Hyuk
DH
D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000302:isolation & purification*; D004355:Drug Stability; D005563:Formic Acid Esters / Q000737:chemistry; D007553:Isotope Labeling / Q000379:methods*; D011786:Quality Control; D019275:Radiopharmaceuticals / Q000138:chemical synthesis / Q000302:isolation & purification; D013936:Thymidine / Q000031:analogs & derivatives* / Q000737:chemistry*
D015224:Dideoxynucleosides; D005563:Formic Acid Esters; D019275:Radiopharmaceuticals; C000345:t-butyloxycarbonyl group; C077504:1-(2'-deoxy-beta-threopentofuranosyl)thymine; C002854:alovudine; D013936:Thymidine