Synthesis of a highly pure lipid core peptide based self-adjuvanting triepitopic group A streptococcal vaccine, and subsequent immunological evaluation

J Med Chem. 2006 Oct 19;49(21):6364-70. doi: 10.1021/jm060475m.

Abstract

We have developed a highly pure, self-adjuvanting, triepitopic Group A Streptococcal vaccine based on the lipid core peptide system, a vaccine delivery system incorporating lipidic adjuvant, carrier, and peptide epitopes into a single molecular entity. Vaccine synthesis was performed using native chemical ligation. Due to the attachment of a highly lipophilic adjuvant, addition of 1% (w/v) sodium dodecyl sulfate was necessary to enhance peptide solubility in order to enable ligation. The vaccine was synthesized in three steps to yield a highly pure product (97.7% purity) with an excellent overall yield. Subcutaneous immunization of B10.BR (H-2(k)) mice with the synthesized vaccine, with or without the addition of complete Freund's adjuvant, elicited high serum IgG antibody titers against each of the incorporated peptide epitopes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antigens, Bacterial / chemistry*
  • Antigens, Bacterial / immunology
  • Bacterial Outer Membrane Proteins / chemistry*
  • Bacterial Outer Membrane Proteins / immunology
  • Carrier Proteins / chemistry*
  • Carrier Proteins / immunology
  • Epitopes
  • Female
  • Immunoglobulin G / blood
  • Lipids / chemistry*
  • Mice
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Peptides / immunology
  • Streptococcal Vaccines / chemical synthesis*
  • Streptococcal Vaccines / immunology
  • Streptococcus pyogenes / immunology*
  • Vaccination
  • Vaccines, Subunit / chemical synthesis
  • Vaccines, Subunit / immunology

Substances

  • Antigens, Bacterial
  • Bacterial Outer Membrane Proteins
  • Carrier Proteins
  • Epitopes
  • Immunoglobulin G
  • Lipids
  • Peptides
  • Streptococcal Vaccines
  • Vaccines, Subunit
  • streptococcal M protein