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Design and synthesis of enantiopure 18 F‐labelled [ 18 F]trifluoromethyltryptophan from 2‐halotryptophan derivatives via copper(I)‐mediated [ 18 F]trifluoromethylation and evaluation of its in vitro characterization for the serotonergic system imaging
Author(s) -
Kim Ho Young,
Lee Ji Youn,
Lee YunSang,
Jeong Jae Min
Publication year - 2019
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.3772
Subject(s) - chemistry , trifluoromethylation , enantiopure drug , serotonergic , yield (engineering) , radiochemistry , stereochemistry , nuclear chemistry , trifluoromethyl , medicinal chemistry , organic chemistry , serotonin , catalysis , biochemistry , enantioselective synthesis , receptor , alkyl , materials science , metallurgy
We synthesized [ 18 F]trifluoromethyl‐ l ‐tryptophan ([ 18 F]CF 3 ‐ l ‐Trp) using Cu(I)‐mediated [ 18 F]trifluoromethylation to image serotonergic system. Radiochemical yield was 6 ± 1.5% (n = 9), and radiochemical purity was over 99%. The molar activity was 0.44 to 0.76 GBq/μmol. [ 18 F]CF 3 ‐ l ‐Trp was stable for up to 6 hours in mouse and human sera at 37°C. Protein‐binding was 0.26 ± 0.03% and 0.34 ± 0.02% in human and mouse serum at 60 minutes, respectively. In conclusion, enantiopure [ 18 F]CF 3 ‐ l ‐Trp was synthesized as a feasible imaging agent for the serotonergic system.