Optimization, Production, and Characterization of a CpG-Oligonucleotide-Ficoll Conjugate Nanoparticle Adjuvant for Enhanced Immunogenicity of Anthrax Protective Antigen

Bioconjug Chem. 2016 May 18;27(5):1293-304. doi: 10.1021/acs.bioconjchem.6b00107. Epub 2016 May 8.

Abstract

We have synthesized and characterized a novel phosphorothioate CpG oligodeoxynucleotide (CpG ODN)-Ficoll conjugated nanoparticulate adjuvant, termed DV230-Ficoll. This adjuvant was constructed from an amine-functionalized-Ficoll, a heterobifunctional linker (succinimidyl-[(N-maleimidopropionamido)-hexaethylene glycol] ester) and the CpG-ODN DV230. Herein, we describe the evaluation of the purity and reactivity of linkers of different lengths for CpG-ODN-Ficoll conjugation, optimization of linker coupling, and conjugation of thiol-functionalized CpG to maleimide-functionalized Ficoll and process scale-up. Physicochemical characterization of independently produced lots of DV230-Ficoll reveal a bioconjugate with a particle size of approximately 50 nm and covalent attachment of more than 100 molecules of CpG per Ficoll. Solutions of purified DV230-Ficoll were stable for at least 12 months at frozen and refrigerated temperatures and stability was further enhanced in lyophilized form. Compared to nonconjugated monomeric DV230, the DV230-Ficoll conjugate demonstrated improved in vitro potency for induction of IFN-α from human peripheral blood mononuclear cells and induced higher titer neutralizing antibody responses against coadministered anthrax recombinant protective antigen in mice. The processes described here establish a reproducible and robust process for the synthesis of a novel, size-controlled, and stable CpG-ODN nanoparticle adjuvant suitable for manufacture and use in vaccines.

MeSH terms

  • Adjuvants, Immunologic / chemistry*
  • Animals
  • Antigens, Bacterial / immunology*
  • Bacterial Toxins / immunology*
  • Drug Design*
  • Drug Stability
  • Ficoll / chemistry*
  • Humans
  • Maleimides / chemistry
  • Methylation
  • Mice
  • Nanoparticles / chemistry*
  • Oligodeoxyribonucleotides / chemistry*
  • Oligodeoxyribonucleotides / immunology*
  • Polyethylene Glycols / chemistry

Substances

  • Adjuvants, Immunologic
  • Antigens, Bacterial
  • Bacterial Toxins
  • CPG-oligonucleotide
  • Maleimides
  • Oligodeoxyribonucleotides
  • anthrax toxin
  • maleimide
  • Ficoll
  • Polyethylene Glycols