Characterization of the spatial arrangement of the two acid-binding sites on the human neutrophil LTB4 receptor

Receptor. 1992 Fall;2(3):169-79.

Abstract

A series of lipophilic benzophenone dicarboxylic acids have been shown to be inhibitors of the binding of LTB4 to its receptors on intact human neutrophils (Gapinski et al. (1990). Structure-activity relationships indicated that maximum activity was achieved when an acid group was attached at the meta position of each ring. In this report, the conformation of these inhibitors that binds best to the LTB4 receptor was determined. Inhibition concentration profiles of four rigid xanthone isomers that mimicked the four major conformational states of this type of benzophenone dicarboxylic acid were compared. LY264086, 3-[4-[7-carboxy-3-[decyloxy]-9-oxo-9H-xanthene]]propanoic acid, was the most potent inhibitor. The distance between the two carboxyl groups in this isomer was found to be 9.8 A, implying that the two acid binding sites on the receptor are separated by similar dimensions. Molecular modeling studies with low energy conformers of the xanthone isomers and LTB4 suggested a configuration of the agonist when it is bound to the receptor but did not exclude all other possibilities. These experiments further support the existence of two acid-binding sites on the human neutrophil LTB4 receptor.

Publication types

  • Comparative Study

MeSH terms

  • Benzophenones / chemistry
  • Benzophenones / pharmacology
  • Binding Sites
  • Humans
  • In Vitro Techniques
  • Leukotriene B4 / chemistry
  • Leukotriene B4 / metabolism*
  • Models, Molecular
  • Molecular Conformation
  • Neutrophils / drug effects
  • Neutrophils / metabolism*
  • Receptors, Immunologic / antagonists & inhibitors
  • Receptors, Immunologic / chemistry
  • Receptors, Immunologic / metabolism*
  • Receptors, Leukotriene B4
  • Structure-Activity Relationship
  • Thermodynamics
  • Xanthenes / chemistry
  • Xanthenes / pharmacology

Substances

  • Benzophenones
  • Receptors, Immunologic
  • Receptors, Leukotriene B4
  • Xanthenes
  • LY 213024
  • Leukotriene B4