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Fluorine-Functionalized Polyphosphazene Immunoadjuvant: Synthesis, Solution Behavior and In Vivo Potency.

Harichandra D Tagad1, Alexander Marin1, Ruixue Wang1

  • 1Institute for Bioscience and Biotechnology Research, University of Maryland, Rockville, MD 20850, USA.

Molecules (Basel, Switzerland)
|May 27, 2023
PubMed
Summary

Fluorine incorporation into polyphosphazene vaccine adjuvants enhances solubility and immunogenicity. This novel fluorinated poly[di(carboxylatophenoxy)phosphazene] (PCPP-F) shows improved antibody responses against Hepatitis C virus antigens.

Keywords:
fluorine-containing pharmaceuticalshepatitis C virushydrolytic degradationpolyelectrolytespolyphosphazenesprotein-polymer interactionssupramolecular self-assemblyvaccine adjuvants

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Area of Science:

  • Polymer Chemistry
  • Vaccine Adjuvant Development
  • Medicinal Chemistry

Background:

  • Fluorine motifs are widely used to enhance drug potency and delivery.
  • This strategy has not been previously applied to vaccine adjuvants.
  • Polyphosphazenes are a class of clinical-stage immunoadjuvants.

Purpose of the Study:

  • To synthesize and characterize a fluorinated analog of the polyphosphazene adjuvant PCPP.
  • To evaluate the impact of fluorination on the adjuvant's properties and immunogenicity.

Main Methods:

  • Synthesis of fluorinated poly[di(carboxylatophenoxy)phosphazene] (PCPP-F).
  • Structural confirmation using NMR spectroscopy (1H, 31P, 19F).
  • Molecular characterization via size-exclusion chromatography and dynamic light scattering.
  • In vivo assessment of immunoadjuvant activity using Hepatitis C virus antigen.

Main Results:

  • PCPP-F was successfully synthesized and characterized.
  • Fluorination improved solubility in acidic solutions and accelerated hydrolytic degradation.
  • The ability of PCPP-F to self-assemble with antigenic proteins was maintained.
  • PCPP-F demonstrated enhanced antibody responses against Hepatitis C virus antigen compared to non-fluorinated PCPP.

Conclusions:

  • Fluorination is a viable strategy to enhance the properties of polyphosphazene vaccine adjuvants.
  • PCPP-F exhibits superior immunoadjuvant activity and improved formulation characteristics.
  • This work opens new avenues for developing advanced macromolecular vaccine adjuvants.