Synthesis and Pharmacological Characterization of [125I]Iodomethyllycaconitine ([125I]Iodo-MLA). A New Ligand for the α7Nicotinic Acetylcholine Receptor

Journal of Medicinal Chemistry
2000.0

Abstract

Nicotinic acetylcholine receptors (nAChRs) are targeted for drug development for cognitive function, Parkinson's disease, analgesia, and other conditions. Currently, [125I]α-bungarotoxin ([125I]α-BGT) is the only iodine-labeled radioligand specific for the α7 nAChR but has high nonspecific binding in filtration assays and cannot cross the blood-brain barrier. Methyllycaconitine (MLA), isolated from Delphinium brownii seeds, is a highly selective α7 nAChR ligand that is a small, reversible-binding compound able to cross the blood-brain barrier. In this study, we synthesized [125I]iodomethyllycaconitine ([125I]-8) via radioiododestannylation of a trimethylstannyl-MLA precursor (9) using chloramine-T as oxidant, achieving a 74% radiochemical yield after HPLC purification. Competition binding experiments showed the iodo-MLA analogue (8) had affinity for the α7 nAChR almost identical to MLA and poor affinity for α4β2 nAChRs labeled by [3H]epibatidine. Saturation binding experiments in rat brain cerebral cortex homogenates revealed saturable specific binding best fit by a one-site model with an affinity constant (Kd) of 1.8 ± 0.4 nM and a maximal binding capacity (Bmax) of 68 ± 3 fmol/mg protein. Competition binding with known ligands (MLA, α-bungarotoxin, 3-cinnamylidine-anabasine) confirmed [125I]-8's specificity for α7 nAChRs, while nicotine, dihydro-β-erythrodine, and mecamylamine were weak or ineffective competitors. Regional binding studies showed selective [125I]-8 binding in α7-rich brain regions (hippocampus, thalamus/hypothalamus) versus low-binding regions (cerebellum, striatum). In summary, [125I]-8 binds with high specificity to α7 nAChRs, serving as a viable alternative to [125I]α-BGT for studying this subtype. Its high specific activity makes it suitable for high throughput screening assays using brain tissue or cloned receptors, and iodine-123 labeling may enable in vivo imaging of α7 nAChRs.

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