Synthesis and Biological Activities of Arginine-vasopressin Analogues with 4-Hydroxyproline in Position 7

Angeliki Buku, Irving L. Schwartz, Nocif Yamin, Herman R. Wyssbrod, Diana Gazis

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

Three arginine-vasopressin (AVP) analogues in which the proline residue in position 7 was substituted with 4-hydroxyproline were synthesized by solid-phase techniques, and their biological activities were evaluated by antidiuretic, pressor, and uterotonic bioassays. The [7-trans-4-hydroxyl-proline]AVP, the l-desamino[7-trans-4-hydroxyl-proline] AVP, and the l-desamino[7-cis-4-hydroxyl-proline]AVP analogues showed a high antidiuretic and strikingly high uterine activity, a sharp decrease in pressor activity, and a better antidiuretic and uterine to pressor selectivity than the parent compound, arginine-vasopressin. The uterine activities are the highest so far assayed in AVP analogues with replacements in position 7.

Original languageEnglish
Pages (from-to)1509-1512
Number of pages4
JournalJournal of Medicinal Chemistry
Volume30
Issue number8
DOIs
StatePublished - 1 Aug 1987
Externally publishedYes

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