Synthesis and some pharmacological properties of the 23-peptide 15-lysine-secretin-(5--27). Special role of the residue in position 15 in biological activity of the vasoactive intestinal polypeptide

J Med Chem. 1978 Nov;21(11):1171-3. doi: 10.1021/jm00209a018.

Abstract

The 23-peptide 15-lysine-secretin-(5-27) [S(5-27)] was synthesized on an insoluble support. The residue in position 15 of secretin, aspartic acid, was replaced by lysine, which occupies that position in the vasoactive intestinal polypeptide (VIP), a member of the secretin family. The resulting analogue showed increased VIP-like activity on smooth muscle preparations and unaltered secretin-like activity on pancreatic juice secretion in the rat. The affinity of the new analogue was high-affinity secretin receptors in acinar cells from guinea pig pancreas was less than that of S(5-27) but was higher than that of S(5-27) for high-affinity VIP receptors in the same cells.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Gastrointestinal Hormones / pharmacology*
  • Guinea Pigs
  • In Vitro Techniques
  • Muscle Relaxation / drug effects
  • Muscle, Smooth / drug effects
  • Pancreas / drug effects
  • Pancreas / metabolism
  • Rats
  • Receptors, Cell Surface / drug effects
  • Secretin / analogs & derivatives*
  • Secretin / chemical synthesis
  • Secretin / pharmacology
  • Structure-Activity Relationship
  • Vasoactive Intestinal Peptide / pharmacology*

Substances

  • Gastrointestinal Hormones
  • Receptors, Cell Surface
  • Secretin
  • Vasoactive Intestinal Peptide