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Article << Previous     |     Next >>   Contents Vol 61(6)

Synthesis and In-Vivo Evaluation of [11C]p-PVP-MEMA as a PET Radioligand for Imaging Nicotinic Receptors

Frédéric Dollé A, Sandrine Langle A, Gaëlle Roger A, Roger R. Fulton B, Béatrice Lagnel-de Bruin A, David J. Henderson B, Françoise Hinnen A, Taliesha Paine C, Mark J. Coster D, Heric Valette A, Michel Bottlaender A, Michael Kassiou C E F G

A CEA, Service Hospitalier Frédéric Joliot, Institut d’Imagerie Biomédicale, 4 Place du Général Leclerc, F-91401 Orsay, France.
B Department of PET and Nuclear Medicine, Royal Prince Alfred Hospital, Missenden Road, Camperdown, NSW 2050, Australia.
C School of Chemistry, University of Sydney, NSW 2006, Australia.
D Eskitis Institute for Cell and Molecular Therapies, Griffith University, Don Young Rd, Nathan, Qld 4121, Australia.
E Discipline of Medical Radiation Sciences, University of Sydney, NSW 2006, Australia.
F Brain and Mind Research Institute, 100 Mallett St, Camperdown, NSW 2050, Australia.
G Corresponding author. Email: m.kassiou@usyd.edu.au
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Within the class of (4-pyridinyl)vinylpyridines developed by Abbott laboratories as potent neuronal nicotinic acetylcholine receptor ligands, p-PVP-MEMA ({(R)-2-[6-chloro-5-((E)-2-pyridin-4-ylvinyl)pyridin-3-yloxy]-1-methylethyl}methylamine) is the lead compound of a novel series that do not display the traditional nicotinic-like pyrrole-ring but still possessing high subnanomolar affinity (Ki 0.077 nm—displacement of [3H](–)cytisine from whole rat brain synaptic membranes). In the present study, p-PVP-MEMA and its nor-derivative ({(R)-2-[6-chloro-5-((E)-2-pyridin-4-ylvinyl)pyridin-3-yloxy]-1-methylethyl}methylamine) as precursor for labelling with the short-lived positron-emitter carbon-11 (T1/2 20.4 min) were synthesized in 10 chemical steps from 2-hydroxy-5-nitropyridine and Boc-d-alanine. N-Alkylation of nor-p-PVP-MEMA with [11C]methyl iodide afforded [11C]p-PVP-MEMA (>98% radiochemically pure, specific activity of 86.4 GBq μmol–1) in 2% (non-decay corrected and non-optimized) radiochemical yield, in 34 min (including HPLC purification and formulation). Preliminary positron emission tomography (PET) results obtained in a Papio hamadryas baboon showed that [11C]p-PVP-MEMA is not a suitable PET-radioligand.

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