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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Substituted Polyesters by Thiol-Ene Modification: Rapid Diversification for Therapeutic Protein Stabilization.

Emma M Pelegri-O'Day1, Samantha J Paluck1, Heather D Maynard1

  • 1Department of Chemistry and Biochemistry and California NanoSystems Institute, University of California, Los Angeles , 607 Charles E. Young Drive East, Los Angeles, California 90095, United States.

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Novel degradable polymers were synthesized to stabilize therapeutic proteins like granulocyte colony-stimulating factor (G-CSF) against temperature fluctuations during storage and shipping. Trehalose- and zwitterion-substituted polyesters showed the most promise for protein stabilization.

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Area of Science:

  • Polymer Chemistry
  • Biomaterials Science
  • Protein Stabilization

Background:

  • Therapeutic proteins are often unstable to storage and shipping temperatures, increasing costs.
  • Novel stabilizers are crucial for maintaining protein integrity in research and industry.

Purpose of the Study:

  • To design and synthesize novel degradable polymers for stabilizing therapeutic proteins against environmental stressors.
  • To evaluate the efficacy of various pendant groups on polycaprolactones for protein stabilization.

Main Methods:

  • Synthesized alkene-substituted degradable polycaprolactones via ring-opening polymerization (ROP) using an organocatalyst.
  • Installed pendant groups including trehalose, lactose, glucose, carboxybetaine, and oligo(ethylene glycol) via thiol-ene reactions.
  • Assessed polymer stabilization of granulocyte colony-stimulating factor (G-CSF) at 4 °C and 60 °C.

Main Results:

  • Trehalose- and zwitterion-substituted polyesters demonstrated the best stabilization for G-CSF.
  • Molecular weight was critical for stabilization at elevated temperatures (60 °C) but less so at refrigeration (4 °C).
  • Degraded polymers and their products were found to be noncytotoxic.

Conclusions:

  • Developed biocompatible, degradable polymers offer a promising platform for stabilizing therapeutic proteins like G-CSF.
  • The synthesized polymers effectively protect proteins from temperature-induced degradation during storage and shipping.
  • This research provides a general strategy for discovering new polymeric protein stabilizers.