Synthesis and biological evaluation of a new class of vaccine adjuvants: aminoalkyl glucosaminide 4-phosphates (AGPs)

Bioorg Med Chem Lett. 1999 Aug 2;9(15):2273-8. doi: 10.1016/s0960-894x(99)00374-1.

Abstract

A novel series of acylated omega-aminoalkyl 2-amino-2-deoxy-4-phosphono-beta-D-glucopyranosides (aminoalkyl glucosaminide 4-phosphates) was synthesized and screened for immunostimulant activity. Several of these compounds enhance the production of tetanus toxoid-specific antibodies in mice and augment vaccine-induced cytotoxic T cells against EG.7-ova target cells.

Publication types

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

MeSH terms

  • Adjuvants, Immunologic / chemical synthesis*
  • Adjuvants, Immunologic / metabolism
  • Animals
  • Antibody Formation / drug effects
  • Cytokines / metabolism
  • Glucosamine / analogs & derivatives*
  • Glucosamine / chemical synthesis
  • Glucosamine / pharmacology
  • Humans
  • Macrophages / drug effects
  • Macrophages / metabolism
  • Mice
  • Mice, Inbred C57BL
  • Mice, Inbred DBA
  • Monocytes / drug effects
  • Monocytes / metabolism
  • Nitric Oxide Synthase / metabolism
  • Nitric Oxide Synthase Type II
  • Rabbits
  • Structure-Activity Relationship
  • Sugar Phosphates / chemical synthesis*
  • Sugar Phosphates / pharmacology
  • Tetanus Toxoid / immunology

Substances

  • Adjuvants, Immunologic
  • Cytokines
  • Sugar Phosphates
  • Tetanus Toxoid
  • NOS2 protein, human
  • Nitric Oxide Synthase
  • Nitric Oxide Synthase Type II
  • Nos2 protein, mouse
  • Glucosamine