Isolation and characterization of α-conotoxin LsIA with potent activity at nicotinic acetylcholine receptors

Biochem Pharmacol. 2013 Sep 15;86(6):791-9. doi: 10.1016/j.bcp.2013.07.016. Epub 2013 Aug 4.

Abstract

A new α-conotoxin LsIA was isolated from the crude venom of Conus limpusi using assay-guided RP-HPLC fractionation. Synthetic LsIA was a potent antagonist of α3β2, α3α5β2 and α7 nAChRs, with half-maximal inhibitory concentrations of 10, 31 and 10 nM, respectively. The structure of LsIA determined by NMR spectroscopy comprised a characteristic disulfide bond-stabilized α-helical structure and disordered N-terminal region. Potency reductions of up to 9-fold were observed for N-terminally truncated analogues of LsIA at α7 and α3β2 nAChRs, whereas C-terminal carboxylation enhanced potency 3-fold at α3β2 nAChRs but reduced potency 3-fold at α7 nAChRs. This study gives further insight into α-conotoxin pharmacology and the molecular basis of nAChR selectivity, highlighting the influence of N-terminal residues and C-terminal amidation on conotoxin pharmacology.

Keywords: 1-(5-chloro-2,4-dimethoxyphenyl)-3-(5-methylisoxazol-3-yl)urea; 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; ACh; AChBP; AFU; CCD; CYANA; Conus limpusi; DIPEA; DMSO; DQF-COSY; EDTA; Electrophysiology; FBS; FLIPR; G protein-coupled receptor; GPCR; HBTU; IC(50); N,N-diisopropylethylamine; NMR; NMR structure; NOESY; Nicotinic acetylcholine receptor; PNU-12596; RP-HPLC; RPMI; Rosewell Park Memorial Institute; TFA; TIPS; TOCSY; acetylcholine; acetylcholine binding protein; arbitrary fluorescent units; charge coupled device; combined assignment and dynamics algorithm for NMR applications; dimethylsulfoxide; double quantum filtered correlation spectroscopy; ethylenediaminetetraacetic acid; fluorometric imaging plate reader; foetal bovine serum; half-maximal inhibitory concentration; nAChR; nicotinic acetylcholine receptor; nuclear magnetic resonance; nuclear overhauser effect spectroscopy; reverse phase-high performance liquid chromatography; total correlation spectroscopy; trifluoroacetic acid; triisopropylsilyl; α-Conotoxin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Calcium / metabolism
  • Cell Line, Tumor
  • Chromatography, Reverse-Phase
  • Conotoxins / chemical synthesis
  • Conotoxins / chemistry
  • Conotoxins / isolation & purification*
  • Conotoxins / pharmacology
  • Conus Snail / chemistry*
  • Fluorescent Dyes
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Nicotinic Antagonists / chemical synthesis
  • Nicotinic Antagonists / chemistry
  • Nicotinic Antagonists / isolation & purification*
  • Nicotinic Antagonists / pharmacology
  • Protein Isoforms / antagonists & inhibitors
  • Protein Isoforms / metabolism
  • Protein Structure, Secondary
  • Quantitative Structure-Activity Relationship
  • Receptors, Nicotinic / metabolism*
  • Substrate Specificity

Substances

  • Conotoxins
  • Fluorescent Dyes
  • Nicotinic Antagonists
  • Protein Isoforms
  • Receptors, Nicotinic
  • Calcium