[en] L-p-[18F]fluorophenylalanine was designed as a potential marker for probing protein synthesis in the human brain by positron emission tomography. This radiotracer has been synthesized using nucleophilic displacement of the activated nitro group of p-nitrobenzaldehyde by NCA 18F- obtained from the 18O (p, n) reaction on enriched water. The L-form of the [18F]fluoroamino acid can be separated on an analytical scale chiral column. A typical production run of 22.2 GBq (600 mCi) of 18F obtained after a 10 microA.h bombardment of 18 MeV protons on 99.8% 18O-enriched water leads to a batch of 1.11 GBq (30 mCi) of NCA L-p-[18F]fluorophenylalanine after a total synthesis time of 120 min.
Disciplines :
General & internal medicine
Author, co-author :
Lemaire, Christian ; Université de Liège - ULiège > Centre de recherches du cyclotron
Guillaume, Marcel ; Université de Liège - ULiège > Département de physique > Spectroscopie atomique et Physique des atomes froids
Christiaens, Léon ; Université de Liège - ULiège > Services généraux (Faculté des sciences) > Relations académiques et scientifiques (Sciences)
Palmer, Anthony ; Université de Liège - ULiège > Unités de recherche interfacultaires > GIGA-CRC In vivo Imaging (Centre de Recherche du Cyclotron)
Cantineau, Robert ; Université de Liège - ULiège > Unités de recherche interfacultaires > GIGA-CRC In vivo Imaging (Centre de Recherche du Cyclotron)
Language :
English
Title :
A New Route for the Synthesis of [18f]Fluoroaromatic Substituted Amino Acids: No Carrier Added L-P-[18f]Fluorophenylalanine
Publication date :
1987
Journal title :
International Journal of Radiation Applications and Instrumentation. Part A, Applied Radiation and Isotopes
Attina, Cacace, Wolf (1983) Labelled aryl fluorides from the nucleophilic displacement of activated nitro groups by 18F-fluoride. J. Labelled Compd. Radiopharm. 20:501.
Arnstein, Richmond (1964) The utilisation of p-fluorophenylalanine for protein synthesis by the phenylalanine-incorporation system from rabbit reticulocytes. Biochem. J. 91:340.
Axelrod, Saavedra (1974) Octopamine, phenylethylamine and tryptamine in the brain. Ciba Found. Symp. 22:51.
Bodsch, Coenen, Stöcklin, Takahashi, Hossmann (1987) Biochemical and autoradiographic study of cerebral protein synthesis with 18F- and 14C-fluorophenylalanine. J. Neurochem., (Submitted); .
Coenen, Bodsch, Takahashi, Hossmann, Stöcklin (1985) Synthesis, autoradiography and biochemistry of l-[18F]fluorophenylalanines for probing protein synthesis. Proc. Eur. Nuclear Medicine Congress, 3–6 Sept. 1985, London; .
Coenen, Franken, Metwally, Stöcklin (1986) Electrophilic radiofluorination of aromatic compounds with [18F] F2 and [18F] CH3COOF and regioselective preparation of l-p-[18F]fluorophenylalanine. Proc. Sixth Int. Symp. Radiopharm. Chem. , Boston, 1986; 151.
Gal, Millard (1971) The mechanism of inhibition of hydroxylases in vivo by p-chlorophenylalanine the effect of cycloheximide. Biochim Biophys Acta 227:32.
Goulding, Palmer (1972) The preparation of fluorine-18 labelled p-fluorophenylalanine for clinical use. Int. J. Appl. Radiat. Isot. 23:133.
Grierson, Adam (1985) In situ preparation of a chemically bonded chiral stationary phase for the separation of aromatic-amino acid enantiomers. J. Chromatogr. 325:103.
Halldin, Lånström (1984) Synthesis of racemic [3-11C] phenylalanine and [3-11C] Dopa. Int. J. Appl. Radiat. Isot. 35:779.
Hamacher, Coenen, Stöcklin (1986) Efficient stereospecific synthesis of no-carier-added 2-[18F]fluoro-2-deoxy-d-glucose using aminopolyether supported nucleophilic substitution. J Nucl Med 27:235.
Hoyte, Lin, Christman, Atkins, Hauser, Wolf (1971) Organic radiopharmaceuticals labelled with short-lived nuclides III 18F-labeled phenylalanines. J. Nucl. Med. 12:280.
Kaufman (1961) The enzymatic conversion of 4-fluorophenylalanine to tryosine. Biochem. Biophys. Acta. 51:619.
Kilbourn, Jerabeck, Welch (1985) An improved 18O-water target for 18F-fluoride production. Int. J. Appl. Radiat. Isot. 36:327.
Kuczenski, Mandell (1972) Regulatory properties of soluble and particulate rat brain tyrosine hydroxylase. J. Biol. Chem. 247:3114.
Westhead, Boyer (1961) The incorporation of p-fluorophenylalanine into some rabbit enzymes and other proteins. Biochem. Biophys. Acta. 54:145.