Conformationally restricted cyclic analogues of substance P: insight into the receptor binding process

Biochem Biophys Res Commun. 1985 Mar 15;127(2):656-62. doi: 10.1016/s0006-291x(85)80211-4.

Abstract

Three new cyclic substance P analogues were prepared to examine the possible role of a pseudocyclic turn structure for receptor recognition. In the guinea pig isolated ileum [Cys5, Cys11]-SP5-11-NH2 and [Cys6, Cys11]-SP5-11-NH2 were inactive at concentrations up to 100 microM, while [Cys5, Cys6, Nle11]-SP was a weak agonist. The order of relative affinities on the rat brain radioreceptor assay was as follows: [Cys5, Cys6, Nle11]-SP greater than [Cys5, Cys11]-SP5-11-NH2 greater than [Cys6, Cys11]-SP5-11-NH2. We interpret these results to indicate that a pseudocyclic structure of the 5-11 sequence may not be an important factor involved in the receptor recognition of substance P.

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

  • Animals
  • Base Sequence
  • Brain / metabolism
  • Female
  • Guinea Pigs
  • Ileum / metabolism
  • In Vitro Techniques
  • Male
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / metabolism
  • Protein Conformation
  • Radioligand Assay
  • Rats
  • Rats, Inbred Strains
  • Receptors, Neurokinin-1
  • Receptors, Neurotransmitter / metabolism*
  • Structure-Activity Relationship
  • Substance P / analogs & derivatives*
  • Substance P / chemical synthesis
  • Substance P / metabolism

Substances

  • Peptides, Cyclic
  • Receptors, Neurokinin-1
  • Receptors, Neurotransmitter
  • Substance P