Analogs of arginine vasopressin modified in position 3 with (R)-alpha-hydroxymethylphenylalanine

J Pept Res. 1999 May;53(5):554-9. doi: 10.1034/j.1399-3011.1999.00064.x.

Abstract

This study describes the synthesis and some pharmacological properties of three new analogs of arginine vasopressin (AVP) substituted in position 3 with (R)-alpha-hydroxymethylphenylalanine ([R]-HmPhe). All new peptides were tested for vasopressor and antidiuretic as well as uterotonic activity. None of the 3 analogs showed any pressor activity and their uterotonic activity was negligible. Only analog [Mpa1,(R)-HmPhe3]AVP exhibited significant antidiuretic activity.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Arginine Vasopressin / analogs & derivatives*
  • Arginine Vasopressin / chemical synthesis
  • Arginine Vasopressin / chemistry
  • Arginine Vasopressin / pharmacology
  • Deamino Arginine Vasopressin / pharmacology
  • Diuresis / drug effects
  • Female
  • Oxytocin / pharmacology
  • Phenylalanine / analogs & derivatives*
  • Phenylalanine / chemistry
  • Rats
  • Rats, Wistar
  • Structure-Activity Relationship
  • Uterine Contraction / drug effects
  • Vasoconstriction / drug effects
  • Vasopressins / pharmacology

Substances

  • Vasopressins
  • Arginine Vasopressin
  • 4-hydroxymethylphenylalanine
  • Phenylalanine
  • Oxytocin
  • Deamino Arginine Vasopressin