An asymmetric approach to the radiosynthesis of both enantiomers of α-[11C]methyldopa and α-[11C]methyltyrosine for positron emission tomography |
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| Authors: | A. Popkov M. Nádvorník J. Jirman P. Kružberská A. Lyčka T. Weidlich J. Kožíšek M. Breza S. Lehel N. M. Gillings |
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| Affiliation: | (1) Faculty of Health and Social Studies, University of South Bohemia, Branišovská 31, 37005 České Budějovice, Czech Republic;(2) PET & Cyclotron Unit, Copenhagen University Hospital, Blegdamsvej 9, 2100 Copenhagen, Denmark;(3) Department of General and Inorganic Chemistry, Faculty of Chemical Technology, Pardubice University, 53210 Pardubice, Czech Republic;(4) Zentiva a. s., U kabelovny 130, 10201 Praha 10, Czech Republic;(5) Department of Analytical Biochemistry, Institute of Entomology, Branišovská 31, 37005 Ceské Budejovice, Czech Republic;(6) Research Institute for Organic Syntheses, Rybitví 296, 53218 Pardubice 20, Czech Republic;(7) Institute of Environment Protection, Pardubice University, Doubravice 41, 53341 Pardubice, Czech Republic;(8) Department of Physical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, 81237 Bratislava, Slovak Republic |
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| Abstract: | In PET, α-methyl amino acids can play a dual role: a) precursors of neurotransmitters analogues for the study of neurodegenerative diseases; b) non-metabolised analogues of proteinogenic amino acids for the study of amino acids uptake into normal and cancer cells. The difference in the uptake rates during a PET scan could visualise cancer cells in a human body. Clinical applications of such amino acids are strongly limited due to their poor availability. For the synthesis of α-[11C]methyl-tryptohan, an industrial procedure was adopted. All attempts to prepare enantiomerically pure α-[11C]methylated tyrosine failed. We carried out [11C]methylation of metalocomplex synthons derived from protected DOPA or tyrosine. Individual diastereomers were successfully separated by preparative HPLC, diluted with excess of water and extracted on C18 cartridges. Optimisation of the procedure followed by hydrolysis of the complexes and purification of the enantiomers of α-[11C]methylDOPA and α-[11C]methyltyrosine is underway. |
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