PeIA-5466: A Novel Peptide Antagonist Containing Non-natural Amino Acids That Selectively Targets alpha3beta2 Nicotinic Acetylcholine Receptors

Author: Hone, A.J.; Fisher, F.; Christensen, S.; Gajewiak, J.; Larkin, D.; Whiteaker, P.; McIntosh, J.M.

Description: Pharmacologically distinguishing alpha3beta2 nicotinic acetylcholine receptors (nAChRs) from closely related subtypes, particularly alpha6beta2, has been challenging due to the lack of subtype-selective ligands. We created analogs of alpha-conotoxin (alpha-Ctx) PeIA to identify ligand-receptor interactions that could be exploited to selectively increase potency and selectivity for alpha3beta2 nAChRs. A series of PeIA analogs were synthesized by replacing amino acid residues in the second disulfide loop with standard or nonstandard residues and assessing their activity on alpha3beta2 and alpha6/alpha3beta2beta3 nAChRs heterologously expressed in Xenopus laevis oocytes. Asparagine(11) was found to occupy a pivotal position, and when replaced with negatively charged amino acids, selectivity for alpha3beta2 over alpha6/alpha3beta2beta3 nAChRs was substantially increased. Second generation peptides were then designed to further improve both potency and selectivity. One peptide, PeIA-5466, was approximately 300-fold more potent on alpha3beta2 than alpha6/alpha3beta2beta3 and is the most alpha3beta2-selective antagonist heretofore reported.

Subject Headings: Peptide, Nicotonic, Acetylcholine

Publication year: 2019

Journal or book title: Journal of Medicinal Chemistry

Volume: 62

Issue: 13

Pages: 6262-6275

Find the full text : https://pubs.acs.org/doi/abs/10.1021/acs.jmedchem.9b00566

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Type: Journal Article

Serial number: 2971