Ligands and tracers for PET studies of the 5-HT system—current status

C. Crouzel1, M. Guillaume2, L. Barré3, C. Lemaire2, V.W. Pike4
1Service Hospitalier Frédéric Joliot, DRIPP, Commissariat á l'Energie Atomique, Hopital d'Orsay, 91406 Orsay, France
2Centre de Recherches du Cyclotron, Université de Liège, Sart Tilman, 4000 Liége, Belgium
3CEA, DSU/DPTE, CYCERON 14021, Caen, France
4MRC Cyclotron Unit, Hammersmith Hospital, Ducane Road, London W12 OHS, England

Tài liệu tham khảo

Ågren, 1991, Low brain uptake of l-[11C]5-hydroxytryptophan in major depression—a positron emission tomography study on patients and healthy volunteers, Acta Psychiatr. Scand., 83, 449, 10.1111/j.1600-0447.1991.tb05574.x Angelini, 1990, Synthesis of N-(α1, α1, α1-tri[18F]fluoro-m-tolyl)-piperazine. A potent serotonin agonist, J. Labelled Cmpd. Radiopharm., 28, 1441, 10.1002/jlcr.2580281213 Atkins, 1972, Organic radiopharmaceuticals labeled with isotopes of short half-life. 18F-Labeled 5- and 6-fluorotryptophan, J. Nucl. Med., 13, 713 Barré, 1991, Synthesis of [11C]MDL 72222 as a potential radiopharmaceutical for the study of the 5-hydroxytryptamine 3 (5HT3) receptor, J. Labelled Cmpd. Radiopharm., 30, 346 Barnes, 1988, [3H]Zacopride identifies 5-HT3, binding sites in rat entorhinal cortex, Br. J. Pharmacol., 94, 391P Barnes, 1990, Characterization and autoradiographic localization of 5-HT3 receptor recognition sites identified with [3H]-(S)-zacopride in the forebrain of the rat, Neuropharmacology, 29, 1037, 10.1016/0028-3908(90)90110-D Baron, 1985, Pharmacologic studies in man with PET: an investigation using 11C-labelled ketanserin, a 5HT2 receptor antagonist, J. Cereb. Bld Flow Metab., 471, 10.1007/978-3-642-70054-5_70 Baron, 1985, Etude in vivo des récepteurs sérotoninergiques centraux chez l'homme par tomographie à positons, Rev. Neurol. (Paris), 141, 537 Bénavidès, 1985, Quantitative autoradiography of [3H]indalpine binding sites in the rat brain: I. Pharmacological characterization, J. Neurochem., 45, 514, 10.1111/j.1471-4159.1985.tb04018.x Berger, 1978, Carbon-11 labelling of the psychoactive drug O-methyl-bufotenine and its distribution in the animal organism, Eur. J. Nucl. Med., 3, 101, 10.1007/BF00251632 Berger, 1980, Carrier-free 11C formaldehyde: an approach, J. Labelled Cmpd. Radiopharm., 17, 59, 10.1002/jlcr.2580170107 Berger, 1979, Automated synthesis of 11C-labelled radiopharmaceuticals: imipramine, nicotine and methionine, Int. J. Appl. Radial. Isot., 30, 393, 10.1016/0020-708X(79)90049-8 Berridge, 1983, 11C-Labelled ketanserin: a selective serotonin S2 antagonist, J. Labelled Cmpd. Radiopharm., 20, 73, 10.1002/jlcr.2580200110 Bjurling, 1989, Synthesis of some 11C-labelled fluoro- and methyl-analogues of l-tyrosine and l-tryptophan, Doctoral dissertation at Uppsala University Bjurling, 1990, Enzymatic synthesis of carboxy-11C-labelled l-tyrosine, l-DOPA, l-tryptophan and 5-hydroxy-l-tryptophan, Acta Chem. Scand., 44, 178, 10.3891/acta.chem.scand.44-0178 Bjurling, 1989, Synthesis of β-11C-labelled l-tryptophan and 5-hydroxy-l-tryptophan using a multi-enzymatic reaction route, J. Chem. Soc. Perkins Trans. I, 1331, 10.1039/P19890001331 Bjurling, 1989, Multi-enzymatic syntheses of some 11C-labelled neurotransmitter precursors: tyrosine, DOPA, tryptophan and 5-hydroxytryptophan, J. Labelled Cmpd. Radiopharm., 26, 243, 10.1002/jlcr.25802601110 Blin, 1988, [18F]Setoperone: a new high affinity ligand for positron emission tomography study of the serotonin-2 receptors in baboon brain in vivo, Eur. J. Pharmacol., 147, 73, 10.1016/0014-2999(88)90635-8 Blin, 1990, A method for the in vivo investigation of the serotonergic 5-HT2 receptors in the human cerebral cortex using positron emission tomography and 18F-labelled setoperone, J. Neurochem., 54, 1744, 10.1111/j.1471-4159.1990.tb01229.x Boegesoe, 1990 Bradley, 1986, Proposals for the classification and nomenclature of functional receptors for 5-hydroxytryptamine, Neuropharmacology, 25, 563, 10.1016/0028-3908(86)90207-8 Chaly, 1988, Synthesis of “no-carrieradded” α-[11C]methyl-l-tryptophan, J. Nucl. Med., 29, 370 Chirakal, 1988, Synthesis of F-18 labelled fluoromelatonins and 5-hydroxy-fluoro-tryptophans, J. Labelled Cmpd. Radiopharm., 25, 63, 10.1002/jlcr.2580250108 Clark, 1973, The preparation of fluorine-18 labelled compounds using a recirculatory neon target, Radiochem. Radioanalyt. Lett., 14, 101 Coenen, 1988, PET measurement of D2 and S2 receptor binding of 3-N-(2′-18F]fluoroethyl)spiperone in baboon brain, Eur. J. Nucl. Med., 14, 80, 10.1007/BF00253446 Crouzel, 1987, Recommendations for a practical production of [11C]methyl iodide, Appl. Radiat. Isot., 38, 601, 10.1016/0883-2889(87)90123-7 Crouzel, 1988, Labelling of a serotonergic ligand with 18F: [18F]setoperone, J. Labelled Cmpd. Radiopharm., 25, 403, 10.1002/jlcr.2580250407 Crouzel, 1988, Labelling of a new serotoninergic ligand with 18F: [18F]ritanserin, J. Labelled Cmpd. Radiopharm., 25, 827, 10.1002/jlcr.2580250804 Dannals, 1990, Synthesis of a selective serotonin uptake inhibitor: [11C]citalopram, Appl. Radial. Isot., 41, 541, 10.1016/0883-2889(90)90036-G Dannals, 1989, Synthesis of a radiotracer for studying serotonin-2 receptors: carbon-11 labeled N-methylketanserin, J. Labelled Cmpd. Radiopharm., 26, 195, 10.1002/jlcr.2580260187 Dannals, 1989, Synthesiś of a radiotracer for studying serotonin uptake sites: carbon-11 labelled N-methylparoxetine, J. Labelled Cmpd. Radiopharm., 26, 205, 10.1002/jlcr.2580260192 Dennis, 1988, Distribution of central ω1 (benzodiazepine1) and ω2 (benzodiazepine2) receptor subtypes in the monkey and human brain. An autoradiographic study with 3H-flunitrazepam and the ω1 selective ligand 3H-zolpidem, J. Pharmacol. Exp. Ther., 247, 309 Denutte, 1983, The production in high yield of N′-(4-[11C]methyl)-imipramine, J. Nucl. Med., 24, 1185 Dumius, 1988, A non-classical 5-hydroxytryptamine receptor positively coupled with adenylate cyclase in the central nervous system, Molec. Pharmacol., 34, 880 Fowler, 1977, 11C-Serotonin: a tracer for the pulmonary endothelial extraction of serotonin, J. Labelled Cmpd. Radiopharm., 13, 194 Fozard, 1984, MDL 72222; a potent and highly selective antagonist at neuronal 5-hydroxytryptamine receptors, Naunynm-Schmiedebergs Arch. Pharmacol., 326, 36, 10.1007/BF00518776 Fozard, 1987, 5-HT: the enigma variations, Trends Pharmacol. Sci., 8, 501, 10.1016/0165-6147(87)90047-2 Frazer, 1990, Subtypes of receptors for serotonin, Ann. Rev. Pharmacol. Toxicol., 30, 307, 10.1146/annurev.pa.30.040190.001515 Frost, 1986, Imaging neuronal biochemistry by emission computed tomography: focus on neuroreceptors, Trends Pharmacol. Sci., 7, 490, 10.1016/0165-6147(86)90435-9 Gaddum, 1957, Two kinds of tryptamine receptor, Br. J. Pharmacol., 12, 323 Glennon, 1986, Central serotonin receptors as targets for drug research, J. Med. Chem., 30, 1, 10.1021/jm00384a001 Guillaume, 1991, Recommendations for fluorine-18 production, Appl. Radial. Isot., 42, 749, 10.1016/0883-2889(91)90179-5 Hansch, 1979, The FRAGMENT method of calculating partition coefficients Hartvig, 1992, Brain kinetics of 11C-labelled tryptophan and 5-hydroxytryptophan in the brain of the Rhesus monkey measured with positron emission tomography, J. Neural Transm., 10.1007/BF01245032 Hartvig, 1992, Positron emission tomographic studies on the selectivity and saturation of 5-hydroxy-L-tryptophan de-carboxylase in the monkey brain, J. Neural. Transm. Hashimoto, 1990, Evaluation of [3H]paroxetine as a radioligand for in vivo study of 5-hydroxytryptamine uptake sites in mouse brain, Radioisotopes, 39, 335, 10.3769/radioisotopes.39.8_335 Hashimoto, 1990, Reduction of in vivo binding of [3H]paroxetine in mouse brain by 3,4-methylenedioxymethamphetamine, Neuropharmacology, 29, 633, 10.1016/0028-3908(90)90024-L Hashimoto, 1990, In vivo labelling of 5-hydroxytryptamine uptake sites in mouse brain with [3H]-6-nitroquipazine, J. Pharmacol. Exp. Ther., 255, 146 Hashimoto, 1987, Synthesis and evaluation of [11C]cyanimipramine, Nucl. Med. Biol., 14, 587 Hayes, 1978, Synthesis and purification of 11C-carboxyl-labeled amino acids, Int. J. Appl. Radial. Isot., 29, 186, 10.1016/0020-708X(78)90142-4 Hoyer, 1989, Species difference in the pharmacology of terminal 5-HT autoreceptors in mammalian brain, Trends Pharmacol. Sci., 10, 130, 10.1016/0165-6147(89)90159-4 Hoyer, 1986, Serotonin receptors in the human brain. I. Characterization and autoradiographic localization of 5-HT1A recognition sites. Apparent absence of 5-HT1B recognition sites, Brain Res., 376, 85, 10.1016/0006-8993(86)90902-9 Hoyer, 1989, 5-HT3, recognition sites in the central and peripheral nervous system: autoradiographic and radioligand binding studies, Br. J. Pharmacol., 96, 7 Hrdina, 1984, Differentiation of two components of specific [3H]imipramine binding in rat brain, Eur. J. Pharmacol., 102, 481, 10.1016/0014-2999(84)90569-7 Hume, 1989, Sertraline and paroxetine fail tests in vivo as 5-HT reuptake site ligands for PET, J. Cereb. Bld Flow Metab., 9, S117 Hume, 1991, Citalopram: labelling with carbon-11 and evaluation in rat as a potential radioligand for in vivo PET studies of 5-HT re-uptake sites, Nucl. Med. Biol., 18, 339 Hume, 1992 Hyttel, 1982, Citalopram-pharmacological profile of a specific serotonin uptake inhibitor with antidepressant activity, Prog. Neuro-Psychopharmacol. Biol. Psychiatr., 6, 277, 10.1016/S0278-5846(82)80179-6 Kilbourn, 1989, Synthesis of radiolabeled inhibitors of pre-synaptic monoamine uptake systems: [18F]GBR 13119 (DA) [11C]nisoxetine (NE), and [11C]fluoxetine (5-HT), J. Labelled Cmpd. Radiopharm., 26, 412, 10.1002/jlcr.25802601177 Kilpatrick, 1987, Identification and distribution of 5-HT3 receptors in rat brain using radioligand binding, Nature, 330, 746, 10.1038/330746a0 Kloster, 1984, 11C-Mesulergin, a potential agent for mapping the serotonin receptor: synthesis and animal experiments, J. Labelled Cmpd. Radiopharm., 21, 1155 Lasne, 1989, The radiosynthesis of [N-methyl-11C]-sertraline, Appl. Radiat. Isot., 40, 147, 10.1016/0883-2889(89)90190-1 Lemaire, 1989, N.C.A. Radiofluorination of altanserine, a potential serotonin receptor-binding radiopharmaceutical for positron emission tomography, J. Labelled Cmpd. Radiopharm., 26, 336, 10.1002/jlcr.25802601145 Lemaire, 1992, [18F]Altanserine, a potential radioligand for the study of serotonin receptors: radiolabeling and in vivo biological behaviour in rats, J. Nucl. Med. Leonhardt, 1989, Serotonin 5-HT2 receptors: two states versus two subtypes, J. Neurochem., 53, 316, 10.1111/j.1471-4159.1989.tb07334.x Leonhardt, 1989, Detection of a novel serotonin receptor sub-type (5-HT1E) in human brain: interaction with a GTP-binding protein, J. Neurochem., 53, 465, 10.1111/j.1471-4159.1989.tb07357.x Lever, 1989, Synthesis and in vivo characterization of d-(+)-(N-[11C]methyl)-2-Br-LSD: a radioligand for positron emission tomographic studies of serotonin 5-HT2 receptors, Nucl. Med. Biol., 16, 697 Leysen, 1986, The drug-receptor dissociation time: new tool for drug research. Receptor binding affinity and drug-receptor dissociation profiles of serotonin-S2, dopamine-D2, histamine-H1 antagonists and opiates, Drug Dev. Res., 8, 119, 10.1002/ddr.430080115 Liau, 1991, Characterization of a novel and potent 5-hydroxytryptamine1A receptor antagonist, Pharmacol. Biochem. Behav., 38, 555, 10.1016/0091-3057(91)90013-R Matzke, 1991, Synthesis of 11C-labelled 5-hydroxytryptamine for the measurement of pulmonary endothelial cell function, Appl. Radiat. Isot., 42, 401, 10.1016/0883-2889(91)90145-Q Maziére, 1978, 11C-Clomipramine: synthesis and analysis, J. Radioanalyt. Chem., 45, 453, 10.1007/BF02519613 Mazière, 1992, PET radioligands for dopamine receptors and re-uptake sites: chemistry and biochemistry, Nucl. Med. Biol., 19, 497 Mazière, 1988, Synthesis, affinity and specificity of 18F-setoperone a potential ligand for in-vivo imaging of cortical serotonin receptors, Nucl. Med. Biol., 15, 463 Middlemiss, 1986, Drugs acting at central 5-hydroxy tryptamine a receptors, Vol. 21, 41 Nakamura, 1989, Synthesis of 11C-labelled imipramine and its biodistribution in mice: a potential tracer for positron emission tomography, Chem. Pharm. Bull., 37, 3376, 10.1248/cpb.37.3376 Pascali, 1990, The radiosynthesis of NCA [O-methyl-11C]viqualine through an N-trityl-protected intermediate, as a potential PET radioligand for 5HT re-uptake sites, J. Labelled Cmpd. Radiopharm., 28, 1341, 10.1002/jlcr.2580281114 Pazos, 1987, Mesulergine, a selective serotonin-2 ligand in the rat cortex, does not label these receptors in porcine and human cortex: evidence for species differences in brain serotonin-2 receptors, Eur. J. Pharmacol., 106, 531, 10.1016/0014-2999(84)90056-6 Pazos, 1986, Serotonin receptors in the human brain. Autoradiographic mapping of serotonin-2 receptors, Neuroscience, 21, 123, 10.1016/0306-4522(87)90327-7 Peroutka, 1990, 5-Hydroxytryptamine receptor subtypes, Pharmacol. Toxicol., 67, 373, 10.1111/j.1600-0773.1990.tb00848.x Peroutka, 1988, [3H]Quipazine labels 5-HT3 recognition sites in rat cortical membranes, Eur. J. Pharmacol., 148, 297, 10.1016/0014-2999(88)90579-1 Perry, 1990, Autoradiography of [3H]quipazine in rodent brain, Eur. J. Pharmacol., 187, 75, 10.1016/0014-2999(90)90342-4 Pierce, 1989, Evidence for distinct 5-hydroxytryptamine2 binding subtypes in cortical membrane preparations, J. Neurochem., 52, 656, 10.1111/j.1471-4159.1989.tb09171.x Pinkus, 1989, Characterization of [3H]zacopride binding: inhibition by its (R+) enantiomer (AHR-4964), (S−) enantiomer (AHR-4965), and 5HT3 antagonists, 72 Pinkus, 1989, Association of [3H]zacopride with 5-HT3 binding sites, Eur. J. Pharmacol., 168, 355, 10.1016/0014-2999(89)90797-8 Plenge, 1991, [3H]Citalopram binding to brain and platelet membranes of human and rat, J. Neurochem., 56, 248, 10.1111/j.1471-4159.1991.tb02588.x Ram, 1989, Synthesis of 11C-labelled citalopram, a selective Serotonin uptake inhibitor, Appl. Radial. Isot., 41, 645, 10.1016/0883-2889(90)90078-U Ram, 1986, Rapid reductive-carboxylation of secondary amines, one pot synthesis of N′-(4-11C-methyl)imipramine, Appl. Radiat. Isot., 37, 391, 10.1016/0883-2889(86)90094-8 Rapport, 1947, Purification of the substance which is responsible for vasoconstrictor activity of serum, 6, 184 Reynolds, 1989, Localization of 5-HT3 receptor binding sites in human dorsal vagal complex, Eur. J. Pharmacol., 174, 127, 10.1016/0014-2999(89)90884-4 Sadzot, 1990, Imaging 5HT2 receptors in the human brain with PET and [18F]altanserin. Preliminary results, J. Nucl. Med., 31, 1584 Scheffel, 1990, Paroxetine as an in vivo indicator of 3, 4-methylenedioxmethamphetamine neurotoxicity: a presynaptic serotonergic positron emission tomography ligand?, Brain Res., 527, 89, 10.1016/0006-8993(90)91064-N Schmidt, 1989, Three dimensional steric modelling of the 5-hydroxytryptamine3 receptor pharmacophore, Molec. Pharmacol., 36, 505 Sedvall, 1986, Imaging of neurotransmitter receptors in the living human brain, Arch. Gen. Psychiatr., 43, 995, 10.1001/archpsyc.1986.01800100089012 Suehiro, 1991, Radiosynthesis and evaluation of N-(3-[18F]fluoropropyl)paroxetine as a radiotracer for in vivo labeling of serotonin re-uptake sites by PET, Nucl. Med. Biol., 18, 791 Takahashi, 1985, 11C-Labelling of indolealkylamine alkaloids and the comparative study of their tissue distributions, Int. J. Appl. Radiat. Isot., 36, 965, 10.1016/0020-708X(85)90257-1 Tedroff, 1991, Monoamine precursors in PET research—biochemical issues and functional significance, volume 20, 39 Twarog, 1953, Serotonin content of some mammalian tissues and urine and a method for its determination, Am. J. Physiol., 175, 157, 10.1152/ajplegacy.1953.175.1.157 Vialli, 1933, Cellule enterocromaffini e cellule basigranulose acidofile nei vertebrata, Z. Zelforsch. Microsk. Anat., 19, 743, 10.1007/BF02450276 Waeber, 1989, 5HT3 receptors in the human brain: autoradiographic visualisation using 3H-ICS 205930, Neuroscience, 31, 393, 10.1016/0306-4522(89)90382-5 Wagner, 1986, Quantitative imaging of neuroreceptors in the living human brain, 16, 51 Washburn, 1979, dl-[Carboxyl-11C]tryptophan, a potential agent for pancreatic imaging; production and preclinical investigations, J. Nucl. Med., 20, 857 Watling, 1989, 5HT3 receptor agonists and antagonists, Neurotransmissions, 5, 1 Wong, 1987, Localization of serotonin 5-HT2 receptors in living human brain by positron emission tomography using N-([11C]--methyl)-2-Br LSD, Synapse, 1, 393, 10.1002/syn.890010502 Xiong, 1989, Characterization of a [3H]-5-hydroxytryptamine binding site in rabbit caudate nucleus that differs from the 5-HT1A, 5-HT1B, 5-HT1C and 5-HT1D subtypes, Life Sci., 45, 1433, 10.1016/0024-3205(89)90033-7 Yanai, 1984, 11C-Labelled indolealkylamines as potential serotonin1 receptor mapping agents: synthesis and biodistribution, J. Labelled Cmpd. Radiopharm., 21, 1152