2-Phenylethyl ester and 2-phenylethyl amide derivative analogues of the C-terminal hepta- and octapeptide of cholecystokinin

Int J Pept Protein Res. 1988 Nov;32(5):384-95. doi: 10.1111/j.1399-3011.1988.tb01273.x.

Abstract

Syntheses of analogues of the C-terminal octa- and heptapeptide of cholecystokinin are described. These analogues were obtained by replacing the C-terminal phenylalanine residue by 2-phenylethyl alcohol or by 2-phenylethylamine derivatives and by replacing the tryptophan residue by a D-tryptophan. The CCK-derivatives were tested for their ability to inhibit binding of labeled CCK-8 to rat pancreatic acini and to guinea pig brain membranes, and for their action on stimulation of amylase release from rat pancreatic acini. Some of these derivatives appeared to exhibit only part of the CCK-activity on amylase release, the D-Trp analogues behaving as CCK-antagonists.

Publication types

  • Comparative Study

MeSH terms

  • Amino Acid Sequence
  • Amylases / metabolism
  • Animals
  • Biological Assay
  • Brain / drug effects
  • Brain / metabolism
  • Cell Membrane / metabolism
  • Chemical Phenomena
  • Chemistry, Physical
  • Esters
  • Guinea Pigs
  • Molecular Sequence Data
  • Pancreas / drug effects
  • Pancreas / metabolism
  • Peptide Fragments / chemical synthesis*
  • Peptide Fragments / pharmacology
  • Phenethylamines*
  • Rats
  • Sincalide / analogs & derivatives*
  • Sincalide / chemical synthesis*
  • Sincalide / metabolism
  • Sincalide / pharmacology
  • Structure-Activity Relationship

Substances

  • Esters
  • Peptide Fragments
  • Phenethylamines
  • cholecystokinin (27-33)
  • phenethylamine
  • Amylases
  • Sincalide