Collect. Czech. Chem. Commun. 1988, 53, 2907-2913

Synthesis, biological activity and receptor binding affinity of two [8-arginine]vasopressin analogues with inhibitory properties

Franciszek Kasprzykowskia, Zbigniew Grzonkaa, Jiřina Slaninováb, Tomislav Barthb, Peter Crausec and Falk Fahrenholzc

a Institute of Chemistry, University of Gdańsk, 80-952 Gdansk, Poland
b Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia
c Max-Planck-Institut für Biophysik, D-6000 Frankfurt a. Main, F.R.G.


Two analogues of arginine-vasopressin: [1-(β-mercapto-β,β-cyclopentamethylenepropionic acid), 2-D-phenylalanine, 7-sarcosine, 8-arginine]vasopressin and [1-(β-mercapto-β,β-cyclopentamethylenepropionic acid), 2-D-phenylalanine, 7-N-methylalanine, 8-arginine]vasopressin were synthesized by solid-phase peptide synthesis method. Both peptides exhibit antioxytocic, antivasopressor and antiglycogenolytic activities, and on the other hand they are weak antidiuretic agonists. The binding affinities of both analogues to oxytocic receptor (guinea pig myometrium membranes) and to hepatic V1 receptor (rat liver membranes) are practically the same as for the parent hormones, whereas the binding affinities to renal V2 receptor (bovine kidney membranes) are 60-90 times lower than for vasopressin.