Synthesis, biological activity, and conformational analysis of [pGlu6,N-MePhe8,Aib9] substance P (6-11): a selective agonist for the NK-3 receptor

Biopolymers. 1993 Jun;33(6):915-26. doi: 10.1002/bip.360330607.

Abstract

A highly potent and selective agonist to the tachykinin NK-3 receptor, [pGlu6,N-MePhe8,Aib9] substance P (6-11) (I), was synthesized via the solid phase method. The ED50 of I was 4 nM in the guinea pig ileum in the absence of atropine (NK-1+NK-3 receptors) and this agonist was 5000-fold less potent in the presence of atropine (NK-1 receptor). The analogue was virtually inactive in the rat vas deferens (NK-2 receptor). A detailed analysis of the solution conformation of this analogue in DMSO-d6 and in a DMSO-d6/H2O cryomixture was carried out by a combination of 1H-nmr 2D techniques (DQF-COSY, TOCSY, NOESY and ROESY) and model building based on empirical energy calculations. Peptide I exists as a mixture of isomers containing cis and trans Phe-N-MePhe peptide bonds. The main isomer, containing a cis Phe-N-MePhe peptide bond, shows a preferred folded conformation characterized by a type VI beta-turn with Phe and N-MePhe in the i + 1 and i + 2 positions. The turn is followed by a helical segment extending to the C-terminal. This conformation is compared to previously reported conformations of other selective tachykinin agonists and may be a promising lead for the design of novel NK-3 agonists with additional conformational constraints.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Guinea Pigs
  • In Vitro Techniques
  • Male
  • Molecular Sequence Data
  • Peptide Fragments / chemical synthesis
  • Peptide Fragments / chemistry*
  • Peptide Fragments / pharmacology
  • Protein Conformation
  • Pyrrolidonecarboxylic Acid / analogs & derivatives
  • Rats
  • Receptors, Neurotransmitter / physiology*
  • Receptors, Tachykinin
  • Substance P / analogs & derivatives*
  • Substance P / chemical synthesis
  • Substance P / chemistry
  • Substance P / pharmacology

Substances

  • Peptide Fragments
  • Receptors, Neurotransmitter
  • Receptors, Tachykinin
  • substance P (6-11), pGlu(6)-N-MePhe(8)-Aib(9)-
  • Substance P
  • Pyrrolidonecarboxylic Acid