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Preparation of [ 18 F]β‐CFT‐FP and [ 11 C]β‐CFT‐FP, selective radioligands for visualisation of the dopamine transporter using positron emission tomography (PET)
Author(s) -
Kämäräinen EevaLiisa,
Kyllönen Teija,
Airaksinen Anu,
Lundkvist Camilla,
Yu Meixiang,
Någren Kjell,
Sandell Johan,
Langer Oliver,
Vepsäläinen Jouko,
Hiltunen Jukka,
Bergström Kim,
Lötjönen Simo,
Jaakkola Timo,
Halldin Christer
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<1235::aid-jlcr411>3.0.co;2-9
Subject(s) - chemistry , dopamine transporter , yield (engineering) , trifluoromethanesulfonate , high performance liquid chromatography , bromide , radiochemistry , nuclear chemistry , chromatography , transporter , organic chemistry , catalysis , biochemistry , materials science , metallurgy , gene
In this study the N‐fluoropropyl analogue of the cocaine congener β‐CFT ( I ), N‐(3‐fluoropropyl)‐2β‐carbomethoxy‐3β‐(4‐fluorophenyl)nortropane (β‐CFT‐FP, III ), was labelled with 18 F or 11 C. Syntheses of the precursors nor‐β‐CFT ( II ) and β‐CFT‐FP acid ( IV ) as well as III itself are described. [ 18 F]β‐CFT‐FP was prepared starting from I using two different labelling reagents: [ 18 F]fluoropropyl bromide ( V ) and [ 18 F]fluoropropyl tosylate ( VI ). A reversed‐phase HPLC system proved to be effective in separating the labelled product from precursor II . The radiochemical incorporation of V or VI to yield [ 18 F]β‐CFT‐FP ( 18 F ‐ III ) was in general 30–50% and the radiochemical purity was higher than 99%. [ 11 C]β‐CFT‐FP ( 11 C ‐ III ) was synthesised by esterification of IV using [ 11 C]methyl triflate ( VII ). An HPLC‐purification system using a reversed‐phase column proved to be effective in separating the product from the acid precursor. The radiochemical yield starting from [ 11 C]carbon dioxide was 30–40% and the radiochemical purity was better than 99%. 18 F ‐ III and 11 C ‐ III have potential as radioligands for visualisation of the dopamine transporter (DAT) using Positron Emission Tomography (PET). Copyright © 2000 John Wiley & Sons, Ltd.