α-Conotoxin [S9A]TxID Potently Discriminates between α3β4 and α6/α3β4 Nicotinic Acetylcholine Receptors

J Med Chem. 2017 Jul 13;60(13):5826-5833. doi: 10.1021/acs.jmedchem.7b00546. Epub 2017 Jun 21.

Abstract

α3β4 nAChRs have been implicated in various pathophysiological conditions. However, the expression profile of α3β4 nAChRs and α6/α3β4 nAChRs overlap in a variety of tissues. To distinguish between these two subtypes, we redesigned peptide 1 (α-conotoxin TxID), which inhibits α3β4 and α6/α3β4 nAChR subtypes. We systematically mutated 1 to evaluate analogue selectivity for α3β4 vs α6/α3β4 nAChRs expressed in Xenopus laevis oocytes. One analogue, peptide 7 ([S9A]TxID), had 46-fold greater potency for α3β4 versus α6/α3β4 nAChRs. Peptide 7 had IC50s > 10 μM for other nAChR subtypes. Molecular dynamics simulations suggested that Ser-9 of TxID was involved in a weak hydrogen bond with β4 Lys-81 in the α6β4 binding site but not in the α3β4 binding site. When Ser-9 was substituted by an Ala, this hydrogen bond interaction was disrupted. These results provide further molecular insights into the selectivity of 7 and provide a guide for designing ligands that block α3β4 nAChRs.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, N.I.H., Extramural

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Conotoxins / chemistry
  • Conotoxins / pharmacology*
  • Conus Snail / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Dynamics Simulation
  • Nicotinic Antagonists / chemistry
  • Nicotinic Antagonists / pharmacology*
  • Oocytes / metabolism
  • Peptides / chemistry
  • Peptides / pharmacology
  • Rats
  • Receptors, Nicotinic / metabolism*
  • Xenopus laevis

Substances

  • Conotoxins
  • Nicotinic Antagonists
  • Peptides
  • Receptors, Nicotinic
  • nicotinic receptor alpha3beta4
  • nicotinic receptor alpha6