Physicochemically and pharmacokinetically stable nonapeptide KISS1 receptor agonists with highly potent testosterone-suppressive activity

J Med Chem. 2014 Jul 24;57(14):6105-15. doi: 10.1021/jm5005489. Epub 2014 Jul 7.

Abstract

Modifications of metastin(45-54) produced peptide analogues with higher metabolic stability than metastin(45-54). N-terminally truncated nonapeptide 4 ([D-Tyr46,D-Pya(4)47,azaGly51,Arg(Me)53]metastin(46-54)) is a representative compound with both potent agonistic activity and metabolic stability. Although 4 had more potent testosterone-suppressant activity than metastin, it possessed physicochemical instability at pH 7 and insufficient in vivo activity. Instability at pH 7 was dependent upon Asn48 and Ser49; substitution of Ser49 with Thr49 reduced this instability and maintained KISS1 receptor agonistic activity. Furthermore, [D-Tyr46,D-Trp47,Thr49,azaGly51,Arg(Me)53,Trp54]metastin(46-54) (14) showed 2-fold greater [Ca2+]i-mobilizing activity than metastin(45-54) and an apparent increase in physicochemical stability. N-terminal acetylation of 14 resulted in the most potent analogue, 22 (Ac-[D-Tyr46,D-Trp47,Thr49,azaGly51,Arg(Me)53,Trp54]metastin(46-54)). With continuous administration, 22 possessed 10-50-fold more potent testosterone-suppressive activity in rats than 4. These results suggested that a controlled release of short-length KISS1 receptor agonists can suppress the hypothalamic-pituitary-gonadal axis and reduce testosterone levels. Compound 22 was selected for further preclinical evaluation for hormone-dependent diseases.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • CHO Cells
  • Chemistry, Physical
  • Cricetulus
  • Dose-Response Relationship, Drug
  • Humans
  • Kisspeptins / administration & dosage
  • Kisspeptins / chemistry
  • Kisspeptins / pharmacology*
  • Male
  • Molecular Conformation
  • Oligopeptides / administration & dosage
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology*
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, G-Protein-Coupled / agonists*
  • Receptors, Kisspeptin-1
  • Structure-Activity Relationship
  • Testosterone / antagonists & inhibitors*
  • Testosterone / metabolism

Substances

  • KISS1R protein, human
  • Kisspeptins
  • Oligopeptides
  • Receptors, G-Protein-Coupled
  • Receptors, Kisspeptin-1
  • Testosterone