Synthesis and immunostimulating properties of novel adamant-1-yl tripeptides

Chem Biodivers. 2012 Apr;9(4):777-88. doi: 10.1002/cbdv.201100232.

Abstract

The aim of this work was to prepare L- and D-(adamant-1-yl)-Gly-L-Ala-D-isoGln peptides in order to study their adjuvant (immunostimulating) activities. Adjuvant activity of adamant-1-yl tripeptides was tested in the mouse model using ovalbumin as an antigen and in comparison to the peptidoglycan monomer (PGM; β-D-GlcNAc-(1→4)-D-MurNAc-L-Ala-D-isoGln-mesoDAP(εNH(2) )-D-Ala-D-Ala) and structurally related adamant-2-yl tripeptides.

MeSH terms

  • Adamantane / analogs & derivatives*
  • Adamantane / chemical synthesis
  • Adamantane / pharmacology*
  • Adjuvants, Immunologic / chemical synthesis
  • Adjuvants, Immunologic / chemistry*
  • Adjuvants, Immunologic / pharmacology*
  • Animals
  • Mice
  • Oligopeptides / chemical synthesis
  • Oligopeptides / chemistry*
  • Oligopeptides / pharmacology*
  • Ovalbumin / immunology
  • Peptidoglycan / chemistry
  • Peptidoglycan / pharmacology

Substances

  • Adjuvants, Immunologic
  • Oligopeptides
  • Peptidoglycan
  • Ovalbumin
  • Adamantane