Synthesis and biological activity profiles of atrial natriuretic factor (ANF) analogs

Int J Pept Protein Res. 1990 Aug;36(2):156-60. doi: 10.1111/j.1399-3011.1990.tb00959.x.

Abstract

Several analogs of the atrial natriuretic factor (ANF) were synthesized by the solid-phase method using the acetamidomethyl (Acm) group for sulfhydryl protection. The compounds were tested in a receptor binding assay using bovine adrenal zona glomerulosa cell membranes and in the rat diuresis/natriuresis assay. Substitution of tyrosine in position 116 of ANF(101-126) and of the analog [3-Mpr105]ANF(105-126)(3-Mpr = 3-mercaptopropionic acid) did not alter the biological activity profiles and, therefore, these two analogs in radioiodinated form will be useful for enzymatic degradation and clearance studies. Replacement of 3-mercaptopropionic acid with 2-mercaptopropionic acid in [3-Mpr105]ANF(105-126) resulted in an analog with very low potency in both assay systems, presumably as a consequence of the steric bulk and/or local conformational restriction produced by the methyl group attached to the alpha-carbon in position 105. The analog [3-Mpr105,Nva109]ANF(105-126)(Nva = norvaline) showed very low affinity in the receptor binding assay but displayed considerable diuretic/natriuretic activity. The obtained biological activity profiles suggest that in comparison with other ANF peptides the des-amino ANF(105-126) analogs may have a somewhat longer half-life in vivo, or alternatively, may indicate a more complex situation of ANF receptor or binding site heterogeneity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Atrial Natriuretic Factor / chemical synthesis
  • Atrial Natriuretic Factor / chemistry
  • Atrial Natriuretic Factor / pharmacology*
  • Biological Assay
  • Diuretics / chemical synthesis
  • Diuretics / chemistry
  • Diuretics / pharmacology*
  • Female
  • Molecular Sequence Data
  • Peptide Fragments / chemical synthesis
  • Peptide Fragments / chemistry
  • Peptide Fragments / pharmacology*
  • Rats
  • Rats, Inbred Strains
  • Receptors, Atrial Natriuretic Factor
  • Receptors, Cell Surface / metabolism*
  • Structure-Activity Relationship

Substances

  • Diuretics
  • Peptide Fragments
  • Receptors, Cell Surface
  • Atrial Natriuretic Factor
  • Receptors, Atrial Natriuretic Factor