Identifying structural determinants of potency for analogs of apelin-13: integration of C-terminal truncation with structure-activity

Bioorg Med Chem. 2014 Jun 1;22(11):2992-7. doi: 10.1016/j.bmc.2014.04.001. Epub 2014 Apr 13.

Abstract

Apelin peptides function as endogenous ligands of the APJ receptor and have been implicated in a number of important biological processes. While several apelinergic peptides have been reported, apelin-13 (Glu-Arg-Pro-Arg-Leu-Ser-His-Lys-Gly-Pro-Met-Pro-Phe) remains the most commonly studied and reported ligand of APJ. This study examines the effect of C-terminal peptide truncations and comprehensive structure-activity relationship (SAR) for a series of analogs based on apelin-13 in an attempt to develop more potent and stable analogs. C-terminal truncation studies identified apelin-13 (N-acetyl 2-11) amide (9) as a potent agonist (EC50=4.4 nM). Comprehensive SAR studies also determined that Arg-2, Leu-5, Lys-8, Met-11, were key positions for determining agonist potency, whereas the hydrophobic volume of Lys-8 was a specific determinate of activity. Plasma stability studies on the truncated 10-mer peptide 28 (EC50=33 nM) indicated the primary sites of cleavage occurred between Nle-3 and Leu-4 and also between Ala-5 and Ala-6. These new ligands represent the shortest known apelin peptides with good functional potency.

Keywords: APJ; Agonist; Apelin; Function; Peptide; Structure–activity; Truncation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • CHO Cells
  • Cricetulus
  • Intercellular Signaling Peptides and Proteins / chemical synthesis
  • Intercellular Signaling Peptides and Proteins / chemistry*
  • Intercellular Signaling Peptides and Proteins / metabolism
  • Protein Conformation
  • Rats
  • Structure-Activity Relationship

Substances

  • Intercellular Signaling Peptides and Proteins
  • apelin-13 peptide