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A gastrin-releasing peptide antagonist containing A psi (CH2O) amide bond surrogate
W S Saari1, D C Heimbrook, A Friedman
1Department of Medicinal Chemistry, Merck Sharp & Dohme Research Laboratory, West Point, Pennsylvania 19486.
Biochemical and Biophysical Research Communications
|November 30, 1989
Abstract:
The [Leu26-psi(CH2O)Leu27] derivative of N-Ac-GRP20-27-peptide amide was prepared and evaluated as a gastrin-releasing peptide antagonist. This psi(CH2O) derivative was found to be a more potent inhibitor of [3H-Phe15]GRP15-24NH2 binding and N-Ac-GRP20-27NH2 induced mitogenesis in Swiss 3T3 fibroblasts than the related nitrogen analog [Leu13-psi(CH2NH)Leu14] bombesin. Possible reasons for the improved activity of the (CH2O) insert relative to the (CH2NH) group include increased hydrophobicity and a reduced tendency of the oxygen derivative to form hydrogen bonds.