Synthesis and biological activity of nociceptin/orphanin FQ(1-13)NH2 analogues modified in 9 and/or 13 position

Bioorg Med Chem Lett. 2006 Aug 1;16(15):4071-4. doi: 10.1016/j.bmcl.2006.04.086. Epub 2006 May 22.

Abstract

The purpose of the present study was the synthesis and the biological screening of new analogues of N/OFQ(1-13)NH2, the minimal sequence maintaining the same activity as the natural peptide nociceptin. In order to investigate the role of Lys, we substituted Lys at positions 9 and/or 13 by Orn, Dab (diaminobutanoic acid) or Dap (diaminopropanoic acid). The new N/OFQ(1-13)NH2 analogues exerted strong and naloxone-resistant inhibition of electrically evoked contractions of rat vas deferens. Lys replacement with Orn maintained or even enhanced the inhibitory activity, while replacements with Dab and Dap decreased inhibitory activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Opioid Peptides / chemical synthesis*
  • Opioid Peptides / chemistry
  • Opioid Peptides / pharmacology*
  • Peptide Fragments / chemical synthesis*
  • Peptide Fragments / chemistry
  • Peptide Fragments / pharmacology*
  • Receptors, Opioid / drug effects

Substances

  • Opioid Peptides
  • Peptide Fragments
  • Receptors, Opioid
  • nociceptin (1-13) amide