Synthesis, radiolabeling and preliminary in vivo evaluation of [ 18F]FE-PE2I, a new probe for the dopamine transporter

The synthesis, radiosynthesis and preliminary PET evaluation of [18F]6 ( K i = 17 nM) is reported. A new dopamine transporter (DAT) ligand, ( E)- N-(3-iodoprop-2-enyl)-2β-carbofluoroethoxy-3β-(4′-methyl-phenyl) nortropane (FE-PE2I, 6), derived from PE2I ( 1), was prepared and found to be a potent in...

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Published in	Bioorganic & medicinal chemistry letters Vol. 19; no. 16; pp. 4843 - 4845
Main Authors	Schou, Magnus, Steiger, Carsten, Varrone, Andrea, Guilloteau, Denis, Halldin, Christer
Format	Journal Article
Language	English
Published	Amsterdam Elsevier Ltd 15.08.2009 Elsevier
Subjects	Animals Biological and medical sciences Brain - metabolism Contrast media. Radiopharmaceuticals Dopamine Plasma Membrane Transport Proteins - antagonists & inhibitors Dopamine Plasma Membrane Transport Proteins - metabolism Dopamine transporter Fluorine Radioisotopes - chemistry Haplorhini Humans Isotope Labeling Kinetics Medical sciences Nortropanes - chemical synthesis Nortropanes - chemistry Nortropanes - pharmacology PE2I PET Pharmacology. Drug treatments Positron-Emission Tomography Radioligand Radiopharmaceuticals - chemical synthesis Radiopharmaceuticals - chemistry Radiopharmaceuticals - pharmacology Rats Tropane Dopamine transporter PE2I Radioligand Tropane PET Fluorine 18 Ligand Monkey Central nervous system Tissue Membrane transport Primates Chemical synthesis Dopamine Fluorine Isotopes Radiolabelling Rodentia Catecholamine In vivo Vertebrata Mammalia Animal Biogenic amine Distribution Neurotransmitter
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Abstract	The synthesis, radiosynthesis and preliminary PET evaluation of [18F]6 ( K i = 17 nM) is reported. A new dopamine transporter (DAT) ligand, ( E)- N-(3-iodoprop-2-enyl)-2β-carbofluoroethoxy-3β-(4′-methyl-phenyl) nortropane (FE-PE2I, 6), derived from PE2I ( 1), was prepared and found to be a potent inhibitor of rodent DAT in vitro. Compound 6 was radiolabelled with fluorine-18 ( t 1/2 = 109.8 min) for PET studies in monkeys. In vivo PET measurements showed a regional distribution in brain that corresponds to the known distribution of DAT. This binding was specific, reversible and the kinetics of [ 18F] 6 binding in brain were faster than for its lead compound, [ 11C] 1. The possible presence of a hydroxymethyl-radiometabolite formed by oxidation in the 3β-benzylic position of [ 18F] 6 warrants further detailed evaluation of the metabolism of [ 18F] 6. [ 18F] 6 is a potential radioligand for imaging DATs in the human brain with PET.
AbstractList	The synthesis, radiosynthesis and preliminary PET evaluation of [18F]6 ( K i = 17 nM) is reported. A new dopamine transporter (DAT) ligand, ( E)- N-(3-iodoprop-2-enyl)-2β-carbofluoroethoxy-3β-(4′-methyl-phenyl) nortropane (FE-PE2I, 6), derived from PE2I ( 1), was prepared and found to be a potent inhibitor of rodent DAT in vitro. Compound 6 was radiolabelled with fluorine-18 ( t 1/2 = 109.8 min) for PET studies in monkeys. In vivo PET measurements showed a regional distribution in brain that corresponds to the known distribution of DAT. This binding was specific, reversible and the kinetics of [ 18F] 6 binding in brain were faster than for its lead compound, [ 11C] 1. The possible presence of a hydroxymethyl-radiometabolite formed by oxidation in the 3β-benzylic position of [ 18F] 6 warrants further detailed evaluation of the metabolism of [ 18F] 6. [ 18F] 6 is a potential radioligand for imaging DATs in the human brain with PET. A new dopamine transporter (DAT) ligand, (E)-N-(3-iodoprop-2-enyl)-2beta-carbofluoroethoxy-3beta-(4'-methyl-phenyl) nortropane (FE-PE2I, 6), derived from PE2I (1), was prepared and found to be a potent inhibitor of rodent DAT in vitro. Compound 6 was radiolabelled with fluorine-18 (t(1/2)=109.8 min) for PET studies in monkeys. In vivo PET measurements showed a regional distribution in brain that corresponds to the known distribution of DAT. This binding was specific, reversible and the kinetics of [(18)F]6 binding in brain were faster than for its lead compound, [(11)C]1. The possible presence of a hydroxymethyl-radiometabolite formed by oxidation in the 3beta-benzylic position of [(18)F]6 warrants further detailed evaluation of the metabolism of [(18)F]6. [(18)F]6 is a potential radioligand for imaging DATs in the human brain with PET.
Author	Varrone, Andrea Steiger, Carsten Halldin, Christer Guilloteau, Denis Schou, Magnus
Author_xml	– sequence: 1 givenname: Magnus surname: Schou fullname: Schou, Magnus email: magnus.schou@astrazeneca.com organization: Karolinska Institutet, Department of Clinical Neuroscience, Psychiatry Section, Stockholm, Sweden – sequence: 2 givenname: Carsten surname: Steiger fullname: Steiger, Carsten organization: Karolinska Institutet, Department of Clinical Neuroscience, Psychiatry Section, Stockholm, Sweden – sequence: 3 givenname: Andrea surname: Varrone fullname: Varrone, Andrea organization: Karolinska Institutet, Department of Clinical Neuroscience, Psychiatry Section, Stockholm, Sweden – sequence: 4 givenname: Denis surname: Guilloteau fullname: Guilloteau, Denis organization: Inserm U619, Université François Rabelais de Tours, France – sequence: 5 givenname: Christer surname: Halldin fullname: Halldin, Christer organization: Karolinska Institutet, Department of Clinical Neuroscience, Psychiatry Section, Stockholm, Sweden
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Keywords	Dopamine transporter PE2I Radioligand Tropane PET Fluorine 18 Ligand Monkey Central nervous system Tissue Membrane transport Primates Chemical synthesis Dopamine Fluorine Isotopes Radiolabelling Rodentia Catecholamine In vivo Vertebrata Mammalia Animal Biogenic amine Distribution Neurotransmitter
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Snippet	The synthesis, radiosynthesis and preliminary PET evaluation of [18F]6 ( K i = 17 nM) is reported. A new dopamine transporter (DAT) ligand, ( E)-... A new dopamine transporter (DAT) ligand, (E)-N-(3-iodoprop-2-enyl)-2beta-carbofluoroethoxy-3beta-(4'-methyl-phenyl) nortropane (FE-PE2I, 6), derived from PE2I...
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SubjectTerms	Animals Biological and medical sciences Brain - metabolism Contrast media. Radiopharmaceuticals Dopamine Plasma Membrane Transport Proteins - antagonists & inhibitors Dopamine Plasma Membrane Transport Proteins - metabolism Dopamine transporter Fluorine Radioisotopes - chemistry Haplorhini Humans Isotope Labeling Kinetics Medical sciences Nortropanes - chemical synthesis Nortropanes - chemistry Nortropanes - pharmacology PE2I PET Pharmacology. Drug treatments Positron-Emission Tomography Radioligand Radiopharmaceuticals - chemical synthesis Radiopharmaceuticals - chemistry Radiopharmaceuticals - pharmacology Rats Tropane
Title	Synthesis, radiolabeling and preliminary in vivo evaluation of [ 18F]FE-PE2I, a new probe for the dopamine transporter
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