title: Analogs of arginine vasopressin modified in the N-terminal part of the molecule with a conformationally constrained cis-peptide bond motif.
abstract: The present work is part of our studies aimed at clarifying the influence of steric constraints in the N-terminal part of arginine vasopressin (AVP) and its analogs on the pharmacological activity of the resulting peptides. We describe the synthesis of eight new analogs of AVP or [3-mercaptopropionic acid (Mpa)]AVP (dAVP) substituted at positions 2 and 3 or 3 and 4 with two diastereomers of 4-aminopyroglutamic acid. The steric constraints provided by this modification turned out, however, so strong that all the peptides were inactive in all of the bioassays (pressor, antidiuretic and uterotonic tests).
authors.affiliation: Faculty of Chemistry, University of Gdańsk, Sobieskiego 18, 80-952 Gdańsk, Poland. dareks@chem.univ.gda.pl
authors.forename: Dariusz
authors.initials: D
authors.lastname: Sobolewski
authors.forename: Adam
authors.initials: A
authors.lastname: Prahl
authors.forename: Izabela
authors.initials: I
authors.lastname: Derdowska
authors.forename: Jirina
authors.initials: J
authors.lastname: Slaninová
authors.forename: Krzysztof
authors.initials: K
authors.lastname: Kaczmarek
authors.forename: Janusz
authors.initials: J
authors.lastname: Zabrocki
authors.forename: Bernard
authors.initials: B
authors.lastname: Lammek
mesh_terms: D000595:Amino Acid Sequence; D000818:Animals; D001127:Arginine Vasopressin / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology; D001794:Blood Pressure / Q000187:drug effects; D004967:Estrogens / Q000502:physiology; D005260:Female; D008297:Male; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D011487:Protein Conformation; D051381:Rats; D017208:Rats, Wistar; D014599:Uterus / Q000187:drug effects / Q000502:physiology; D014667:Vasopressins / Q000494:pharmacology
chemical_list: D004967:Estrogens; D009842:Oligopeptides; D014667:Vasopressins; D001127:Arginine Vasopressin