A novel linker methodology for the synthesis of tailored conjugate vaccines composed of complex carbohydrate antigens and specific TH-cell peptide epitopes

Chemistry. 2008;14(19):5908-17. doi: 10.1002/chem.200800065.

Abstract

Pathogenic organisms or oncogenically transformed cells often express complex carbohydrate structures at their cell surface, which are viable targets for active immunotherapy. We describe here a novel, immunologically neutral, linker methodology for the efficient preparation of highly defined vaccine conjugates that combine complex saccharide antigens with specific TH-cell peptide epitopes. This novel heterobifunctional approach was employed for the conjugation of a (1-->2)-beta-mannan trisaccharide from the pathogenic fungus Candida albicans as well as the carbohydrate portion of tumor-associated ganglioside GM2 to a TH-cell peptide epitope derived from the murine 60 kDa self heat-shock protein (hsp60). Moreover, the linkage chemistry has proven well suited for the synthesis of more complex target structures such as a biotinylated glycopeptide, a three component vaccine containing an immunostimulatory peptide epitope from interleukin-1 beta (IL-1 beta), and for the conjugation of complex carbohydrates to carrier proteins such as bovine serum albumin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antigens / chemistry
  • Antigens / immunology*
  • Candida albicans / chemistry
  • Candida albicans / immunology
  • Cattle
  • Enzyme-Linked Immunosorbent Assay
  • Epitopes / chemistry
  • Epitopes / immunology*
  • G(M2) Ganglioside / chemistry
  • G(M2) Ganglioside / immunology
  • Glycoconjugates* / chemical synthesis
  • Glycoconjugates* / immunology
  • Heat-Shock Proteins / chemistry
  • Heat-Shock Proteins / immunology
  • Interleukin-1beta / chemistry
  • Interleukin-1beta / immunology
  • Peptides / chemistry
  • Peptides / immunology*
  • T-Lymphocytes, Helper-Inducer / immunology*
  • Vaccines, Conjugate*

Substances

  • Antigens
  • Epitopes
  • Glycoconjugates
  • Heat-Shock Proteins
  • Interleukin-1beta
  • Peptides
  • Vaccines, Conjugate
  • G(M2) Ganglioside