Synthesis of the cardiac inotropic polypeptide anthopleurin-A

Int J Pept Protein Res. 1994 May;43(5):463-70. doi: 10.1111/j.1399-3011.1994.tb00545.x.

Abstract

The sea anemone polypeptide anthopleurin-A (AP-A) at nanomolar concentrations enhances myocardial contractility without affecting automaticity. It has a therapeutic index higher than that of the digitalis glycosides, and may serve as a molecular model for designing a new class of inotropic drugs acting on the myocardial Na channel at site 3. AP-A is a 49 residue peptide crosslinked by three disulfide bonds; its tertiary structure has been determined by NMR. Here we report the solid-phase synthesis of this polypeptide. Synthetic AP-A displayed CD and NMR spectra identical with those of the natural toxin; it possessed 94 +/- 15% of the inotropic activity of natural AP-A. Therefore, it is feasible to prepare various type 1 sea anemone toxin analogs by solid-phase chemical synthesis in order to identify side chains important for peptide folding and interaction with sodium channels.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Atrial Function
  • Cardiotonic Agents / chemical synthesis*
  • Cardiotonic Agents / isolation & purification
  • Cardiotonic Agents / pharmacology
  • Circular Dichroism
  • Electrophoresis
  • Heart Atria / drug effects
  • In Vitro Techniques
  • Intercellular Signaling Peptides and Proteins
  • Male
  • Molecular Sequence Data
  • Myocardial Contraction / drug effects
  • Peptides / chemical synthesis*
  • Peptides / isolation & purification
  • Peptides / pharmacology
  • Rats
  • Rats, Sprague-Dawley
  • Sea Anemones
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Cardiotonic Agents
  • Intercellular Signaling Peptides and Proteins
  • Peptides
  • anthopleurin-A