alpha-Methylproline-containing renin inhibitory peptides: in vivo evaluation in an anesthetized, ganglion-blocked, hog renin infused rat model

J Med Chem. 1987 Mar;30(3):536-41. doi: 10.1021/jm00386a016.

Abstract

A structure-activity analysis of peptides containing backbone C alpha-methyl modification at the P4 site of the angiotensinogen sequence led to the discovery of potent renin inhibitors with apparent in vitro metabolic stability. Boc-alpha-MePro-Phe-His-Leu psi[CHOHCH2]Val-Ile-Amp dicitrate (Va) is a potent inhibitor of human plasma renin with an IC50 value of 1.8 nM. This peptide was shown not to be degraded in vitro by chymotrypsin, elastase, pepsin, and a rat liver homogenate preparation. It is also a potent inhibitor of hog renin with an IC50 value of 1.6 nM and was shown to elicit in vivo activity and cause dose-dependent hypotensive responses when given intravenously to anesthetized ganglion-blocked, hog renin infused rats.

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Chemical Phenomena
  • Chemistry
  • Humans
  • Indicators and Reagents
  • Kinetics
  • Male
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / pharmacology*
  • Proline / analogs & derivatives*
  • Rats
  • Rats, Inbred Strains
  • Renin / antagonists & inhibitors*
  • Renin / blood
  • Swine

Substances

  • Indicators and Reagents
  • Oligopeptides
  • 2-methylproline
  • renin inhibitory peptide
  • Proline
  • Renin