(S)-3-methyl-5-(1-methyl-2-pyrrolidinyl) isoxazole (ABT 418): A novel cholinergic ligand with cognition-enhancing and anxiolytic activities: II. In vivo characterization
Abstract
A diversity of nicotinic acetylcholine receptor (nAChR) subtypes has been identified in mammalian brain using recombinant DNA technology. Alterations in the activity of these acetylcholinegated ion channels have been implicated in a number of central nervous system disorders including Alzheimer's disease (AD). The potential therapeutic usefulness of (-)-nicotine [(S)-3-(1-methyl-2-pyrrolidinyl) pyridine], the prototypic agonist at nAChRs, is severely limited by side effects that are the result of activation of both cholinergic and noncholinergic pathways in the central and peripheral nervous systems. This study sought to determine the in vitro selectivity of (S)-3-methyl-5-(1methyl-2-pyrrolidinyl)isoxazole (ABT 418), a novel analog of (-)-nicotine in which the pyridine ring was replaced with an isoxazole bioisotere, to activate nAChRs. ABT 418 was a potent inhibitor of [3H]-cytisine binding to nAChR in rat brain (Ki = 3 nM) but was inactive (Ki > 10,000 nM) in 37 other receptor/neurotransmitter-uptake/enzyme/transduction system binding assays, including those for alpha-bungarotoxin, muscarinic and 5-hydroxytryptamine3 receptors. In PC12 cells, patch-clamp studies indicated that ABT 418 was an agonist with an EC50 value of 209 microM, a potency to activate cholinergic channel currents some 4-fold less than that of (-)-nicotine (52 microM). Channel current responses elicited by ABT 418 were prevented by the cholinergic channel blocker, mecamylamine. ABT 418 was also approximately 10-fold less potent (EC50 value = 380 nM) than (-)-nicotine (40 nM) in increasing [3H]-dopamine release from rat striatal slices, an effect that was blocked by the nAChR antagonist, dihydro-beta-erythroidine (10 microM).2+ In contrast, ABT 418 appeared equipotent with (-)-nicotine in enhancing 86Rb+ flux from mouse thalamic synaptosomes. ABT 418 demonstrated an in vitro pharmacological profile of cholinergic channel activation that was robust at some nAChR, but not others. The reasons for this are unclear. However, a nAChR subtype selectivity may account for the in vitro potency differences of ABT 418 on various neurotransmitter systems, and the substantial separation between the cognitive enhancement/anxiolytic benefits, and the reduced central nervous system side-effect liabilities seen in vivo. ABT 418 represents the first neuronal nAChR ligand that differentiates the toxicities/liabilities and other negative aspects normally associated with liabilities and other negative aspects normally associated with (-)-nicotine from the potential pharmacological benefits of selective cholinergic channel activation.
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The α4β2 nAChR agonist ABT-418 increased open arm time in the elevated plus maze, and both ABT-418 and the α4β2 partial agonist ABT-089 reversed the anxiogenic effects of nicotine withdrawal.
“an α4β2 nAChR agonist, ABT-418, was found to increase open arm time in the EPM and both ABT-418 and an α4β2 nAChR partial agonist, ABT-089, reversed the anxiogenic effects of nicotine withdrawal (Brioni et al., 1994; Decker et al., 1994; Yohn, Turner, & Blendy, 2014).”
From Nicotine addiction and psychiatric disorders (2015) · cites this paper as Decker et al., 1994
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Simplified quantification of nicotinic receptors with 2[18F]F-A-85380 PET
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Nicotinic Receptors and Attention
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- Authors
- Decker, M. W., Brioni, J. D., Sullivan, J. P., Buckley, M. J., Radek, R. J., Raszkiewicz, J. L., Kang, C. H., Kim, D. J., Giardina, W. J., & Wasicak, J. T.
- Affiliations
- Abbott (United States) (US)
- ORCID
- Decker, M W
- Venue
- The Journal of Pharmacology and Experimental Therapeutics
- Publisher
- Elsevier BV
- Published
- 1994-07
- Volume
- 270
- Issue
- 1
- Pages
- 319-328
- ISSN
- 0022-3565 (ISSN-L)
- OpenAlex
- W2100773070
- Cited by
- 180
- References
- 0
- Citations by year
- 2025: 1 · 2024: 1 · 2022: 1 · 2020: 3 · 2018: 3 · 2017: 1 · 2016: 3 · 2015: 8 · 2014: 1 · 2013: 6 · 2012: 6
- FWCI
- 7.09
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Pharmacology and Experimental Therapeutics (publishedVersion)
- PubMed (publishedVersion)
- PubMed
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Nicotinic Acetylcholine Receptors Study
- Life Sciences › Neuroscience › Cellular and Molecular Neuroscience › Neuroscience and Neuropharmacology Research
- Health Sciences › Medicine › Pharmacology › Cholinesterase and Neurodegenerative Diseases
- Keywords
- ABT-418, cognitive enhancement, anxiolytic effects, avoidance learning, mecamylamine, elevated plus maze, cortical EEG, cholinergic ligands
- MeSH terms
- Quinolizidine Alkaloids, Alkaloids, Animals, Azocines, Binding, Competitive, Cognition, Corpus Striatum, Dopamine, Ion Channels, Isoxazoles, Kinetics, Male, Nicotine, Parasympathomimetics, Pyrrolidines, Quinolizines, Receptors, Cholinergic, Receptors, Nicotinic, Rubidium, Rubidium Radioisotopes, Anti-Anxiety Agents, Tritium, PC12 Cells, Rats, Sprague-Dawley, Mice, Rats
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