[Synthesis and immunomodulating activity of new glycopeptides of glycyrrhizic acid containing residues of L-glutamic acid]

Bioorg Khim. 2006 Nov-Dec;32(6):660-6. doi: 10.1134/s1068162006060136.
[Article in Russian]

Abstract

New glycopeptides of glycyrrhizic acid (GA) containing Glu residues and their alpha-methyl esters, gamma-methyl esters, and alpha,gamma-dimethyl esters were synthesized using N,N'-dicyclohexylcarbodiimide in the presence of N-hydroxybenzotriazole or N-hydroxysuccinimide. Formation of amide bonds was observed on all the three COOH groups of GA, or selectively on the COOH groups of the GA carbohydrate part in dependence on the ratio of reagents and the reaction conditions. The GA glycopeptide with three residues of Glu(OH)-OMe at a dose of 2 mg/kg stimulated the production of antibody-forming cells in mouse spleen in comparison with the control. The GA glycopeptide containing Glu residues only in the GA carbohydrate part turned out to be an immunosuppressor. The glycopeptide of the 30-methyl ester of GA with residues of free Glu in its carbohydrate part increased the hemagglutinine titer at oral doses of 2 and 10 mg/kg. All the studied compounds had practically no effect on the delayed-type hypersensitivity in mice.

Publication types

  • Comparative Study
  • English Abstract
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Antibody Formation / drug effects
  • Antibody Formation / immunology
  • Dose-Response Relationship, Drug
  • Glutamic Acid / chemistry
  • Glutamic Acid / pharmacology
  • Glycopeptides / chemical synthesis*
  • Glycopeptides / chemistry
  • Glycopeptides / pharmacology
  • Glycyrrhizic Acid / analogs & derivatives
  • Glycyrrhizic Acid / chemical synthesis*
  • Glycyrrhizic Acid / chemistry
  • Glycyrrhizic Acid / pharmacology
  • Immunosuppressive Agents / chemical synthesis*
  • Immunosuppressive Agents / chemistry
  • Immunosuppressive Agents / pharmacology
  • Mice
  • Spleen / immunology

Substances

  • Glycopeptides
  • Immunosuppressive Agents
  • Glutamic Acid
  • Glycyrrhizic Acid