Synthesis and biological evaluation of oxytocin analogues containing L-alpha-t-butylglycine [Gly(Bu t)] in positions 8 or 9

Peptides. 2003 Sep;24(9):1425-31. doi: 10.1016/j.peptides.2003.09.007.

Abstract

We report the solid phase synthesis and some pharmacological properties of seventeen new oxytocin (OT) analogues. Basic modification at positions 8 and/or 9 (introduction of L-alpha-t-butylglycine [Gly(Bu(t))]) was combined with D-Cys(6), D-Tyr(Et)(2), Mpa(1) or Pen(1) modifications and their various combinations. We also present properties of two previously reported re-synthesized analogues ([Gly(Bu(t))(8)]OT and [Mpa(1), Gly(Bu(t))(8)]OT). The analogues were tested for rat uterotonic activity in vitro, in the rat pressor assay and for binding affinity to human OTR.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line
  • Female
  • Glycine / analogs & derivatives*
  • Glycine / chemistry*
  • Humans
  • In Vitro Techniques
  • Oxytocin / analogs & derivatives
  • Oxytocin / chemical synthesis*
  • Oxytocin / chemistry
  • Oxytocin / pharmacology*
  • Rats
  • Uterus / drug effects
  • Uterus / physiology

Substances

  • Oxytocin
  • Glycine