Structure-activity relationships of analogues of the wasp toxin philanthotoxin: non-competitive antagonists of quisqualate receptors

Toxicon. 1990;28(11):1333-46. doi: 10.1016/0041-0101(90)90098-r.

Abstract

Fifty-two analogues of the wasp toxin, philanthotoxin-433, have been synthesized and tested on a glutamatergic, nerve-muscle preparation from locust leg. Reduction in amplitude of the neurally-evoked muscle twitch was used to construct dose-inhibition relationships from which IC50S were estimated. The most active analogues were characterized by one or more of the following: increased hydrophobicity of aromatic and tyrosyl regions; an increased number of protonated groups in the polyamine region; a guanidinium instead of a spermine terminal amino moiety. The incorporation of a butyl side-group in the polyamine also enhanced potency. These results are explained on the basis of the known non-competitive antagonistic blockage by philanthotoxin-433 of the channel gated by postjunctional glutamate receptors when the channel is open.

Publication types

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

MeSH terms

  • Animals
  • Female
  • Grasshoppers
  • Molecular Structure
  • Muscles / drug effects
  • Oxadiazoles / metabolism
  • Polyamines*
  • Receptors, AMPA
  • Receptors, Neurotransmitter / antagonists & inhibitors*
  • Structure-Activity Relationship
  • Wasp Venoms / chemistry
  • Wasp Venoms / pharmacology*
  • Wasps

Substances

  • Oxadiazoles
  • Polyamines
  • Receptors, AMPA
  • Receptors, Neurotransmitter
  • Wasp Venoms
  • delta-philanthotoxin