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Abstract
A radiolabeled amino acid O-[18F]fluoromethyl-D-tyrosine (D-[18F]FMT) has been reported to show high tumor uptake. However, introduction of [18F]fluoromethyl group was difficult and was an issue to be solved. We solved it by using a precursor containing 1,2,3-triazolium salt. D-[18F]FMT was synthesized from (R)-1-((4-(2-((tert-butoxycarbonyl)amino)-3-((3,4-dimethylbenzyl)oxy)-3-oxopropyl)phenoxy)methyl)-3-methyl-4-phenyl-1H-1,2,3-triazol-3-ium trifluoromethanesulfonate via intra-molecular 18F-fluorination and subsequent removal of the protecting groups. The total synthesis time was 65min (including purification) and the overall radiochemical yield was 9% based on the isolated product (not decay-corrected). The resulting D-[18F]FMT was obtained with high radiochemical purity (> 99%) and specific activity (100-150 GBq/μmol). D-[18F]FMT also achieved excellent results in pharmacological evaluation such as stability test and protein binding assay. We expect that this simple one-pot labeling method would help using D-[18F]FMT more widely.

Author information

Kim HY1, Park C2, Lee JY3, Chi DY4, Lee YS1, Jeong JM5.
1
Department of Nuclear Medicine, Seoul National University College of Medicine, Seoul, Republic of Korea.
2
Department of Chemistry, Sogang University, Seoul, Republic of Korea.
3
Department of Nuclear Medicine, Seoul National University College of Medicine, Seoul, Republic of Korea; Department of Biomedical Sciences, Seoul National University Graduate School, Seoul, Republic of Korea.
4
Department of Chemistry, Sogang University, Seoul, Republic of Korea. Electronic address: daeyoon.chi@futurechem.co.kr.
5
Department of Nuclear Medicine, Seoul National University College of Medicine, Seoul, Republic of Korea; Department of Biomedical Sciences, Seoul National University Graduate School, Seoul, Republic of Korea; Cancer Research Institute, Seoul National University, Seoul, Republic of Korea. Electronic address: jmjng@snu.ac.kr.