A novel immunostimulator, N-[alpha-O-benzyl-N-(acetylmuramyl)-L-alanyl-D-isoglutaminyl]-N6-trans-(m-nitrocinnamoyl)-L-lysine, and its adjuvancy on the hepatitis B surface antigen

J Med Chem. 2005 Aug 11;48(16):5112-22. doi: 10.1021/jm0493313.

Abstract

N(2)-[alpha-O-benzyl-N-(acetylmuramyl)-L-alanyl-D-isoglutaminyl]-N(6)-trans-(m-nitrocinnamoyl)-L-lysine (muramyl dipeptide C, or MDP-C) has been synthesized as a novel, nonspecific immunomodulator. The present study shows that MDP-C induces strong cytolytic activity by macrophages on P388 leukemia cells and cytotoxic activity by cytotoxic T lymphocytes (CTLs) on P815 mastocytoma cells. Our results also indicate that MDP-C is an effective stimulator for production of interleukin-2 and interleukin-12 by murine bone marrow derived dendritic cells (BMDCs) and production of interferon-gamma by CTLs. Additionally, MDP-C increases the expression levels of several surface molecules, including CD11c, MHC class I, and intercellular adhesion molecule-1 in BMDCs. Moreover, MDP-C remarkably enhances the immune system's responsiveness to hepatitis B surface antigen (HBsAg) in hepatitis B virus transgenic mice for both antibody production and specific HBsAg T-cell responses ex vivo. Our results indicate that MDP-C is an apyrogenic, nonallergenic, and low-toxicity immunostimulator with great potential for diagnostic, immunotherapeutic, and prophylactic applications in diseases such as hepatitis B and cancers.

Publication types

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

MeSH terms

  • Acetylmuramyl-Alanyl-Isoglutamine / adverse effects
  • Acetylmuramyl-Alanyl-Isoglutamine / analogs & derivatives*
  • Acetylmuramyl-Alanyl-Isoglutamine / chemical synthesis
  • Acetylmuramyl-Alanyl-Isoglutamine / pharmacology
  • Adjuvants, Immunologic / adverse effects
  • Adjuvants, Immunologic / chemical synthesis*
  • Adjuvants, Immunologic / pharmacology
  • Animals
  • Antibody Formation
  • Bone Marrow Cells / drug effects
  • Bone Marrow Cells / metabolism
  • CD11c Antigen / biosynthesis
  • Cell Line, Tumor
  • Cytotoxicity, Immunologic
  • Dendritic Cells / drug effects
  • Dendritic Cells / metabolism
  • Hepatitis B / immunology
  • Hepatitis B Surface Antigens / immunology*
  • Hepatitis B Vaccines / immunology
  • Histocompatibility Antigens Class I / biosynthesis
  • In Vitro Techniques
  • Intercellular Adhesion Molecule-1 / biosynthesis
  • Interleukin-12 / biosynthesis
  • Interleukin-2 / biosynthesis
  • Macrophages / drug effects
  • Macrophages / immunology
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Mice, Transgenic
  • Rabbits
  • Rats
  • Rats, Wistar
  • T-Lymphocytes, Cytotoxic / drug effects
  • T-Lymphocytes, Cytotoxic / immunology
  • Toxicity Tests, Acute

Substances

  • Adjuvants, Immunologic
  • CD11c Antigen
  • Hepatitis B Surface Antigens
  • Hepatitis B Vaccines
  • Histocompatibility Antigens Class I
  • Interleukin-2
  • N(2)-(O-benzyl-N-(acetylmuramyl)-alanyl-isoglutaminyl)-N(6)-(3-nitrocinnamoyl)-lysine
  • Intercellular Adhesion Molecule-1
  • Interleukin-12
  • Acetylmuramyl-Alanyl-Isoglutamine