Synthesis of analogues of the Des‐Phe‐NH2C‐terminal hexapeptide of cholecystokinin showing gastrin antagonist activity
- 1 April 1986
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 27 (4) , 386-393
- https://doi.org/10.1111/j.1399-3011.1986.tb01032.x
Abstract
Four analogues of Z-CCK-27-32-NH2,Z-Tyr(SO3-)-Met-Gly-Trp-Met-Asp-NH2, a cholecystokinin receptor antagonist have been synthesized by solution methodology. In these analogues, Z-Tyr(SO3-)-Nle-Gly-Trp-Met-Asp-NH216,Z-Tyr(SO3-)-Nle-Gly-Trp-Nle-Asp-NH2 17, BOC-Tyr(SO3-)-Met-Gly-Trp-Met-Asp-NH2 24 and Boc-Tyr(SO3-)Met-Gly-Trp-Nle-Asp-NH2 25 methionyl residues were replaced by norleucyl residues. Preliminary biological activity on gastrin-induced acid secretion, in rat, are reported. These derivatives proved to antagonize the action of gastrin, with ED50 of between 0.5 and 3 mg/kg.Keywords
This publication has 15 references indexed in Scilit:
- Synthesis of Z‐CCK‐27–32‐NH2, Z‐Tyr(So3‐)‐Met‐Gly‐Trp‐Met‐Asp‐NH2, a cholecystokinin receptor antagonist and an inhibitor of gastrin‐induced acid secretionInternational Journal of Peptide and Protein Research, 1985
- Ceruletide, ceruletide analogues and cholecystokinin octapeptide (CCK-8): Effects on isolated intestinal preparations and gallbladders of guinea pigs and micePeptides, 1984
- The importance of the amino acid in position 32 of cholecystokinin in determining its interaction with cholecystokinin receptors on pancreatic aciniBiochimica et Biophysica Acta (BBA) - General Subjects, 1981
- Cholecystokinin (pancreozymin). 3. Synthesis and properties of an analog of the C-terminal heptapeptide with serine sulfate replacing tyrosine sulfateJournal of Medicinal Chemistry, 1977
- Peptide Coupling Reagents VI1. A Novel, Cheaper Preparation of Benzotriazolyloxytris[dimethylamino]phosphonium Hexafluorophosphate (BOP Reagent)Synthesis, 1976
- N‐Hydroxyverbindungen als Katalysatoren für die Aminolyse aktivierter EsterEuropean Journal of Inorganic Chemistry, 1973
- Synthesis of cholecystokinin-pancreozymin. I. C-terminal dodecapeptideJournal of the American Chemical Society, 1970
- Synthese und Verwendung von tert.‐Butyloxycarbonylfluorid. und anderen Fluorkohlensäureestern zur Darstellung säurelabiler Urethan‐Derivate von AminosäurenEuropean Journal of Organic Chemistry, 1968
- The Use of Esters of N-Hydroxysuccinimide in Peptide SynthesisJournal of the American Chemical Society, 1964
- Action of Sulfating Agents on Proteins and Model Substances. I. Concentrated Sulfuric AcidJournal of the American Chemical Society, 1946