Poly (glycerol adipate) (PGA) backbone modifications with a library of functional diols: Chemical and physical effects

Philippa L. Jacob, Laura A. Ruiz Cantu, Amanda K. Pearce, Yinfeng He, Joachim C. Lentz, Jonathan C. Moore, Fabricio Machado, Geoffrey Rivers, Edward Apebende, Maria Romero Fernandez, Iolanda Francolini, Ricky Wildman, Steven M. Howdle, Vincenzo Taresco

Research output: Journal PublicationArticlepeer-review

4 Citations (Scopus)

Abstract

Enzymatically synthesised poly(glycerol adipate) (PGA) has shown a palette of key desirable properties required for a biomaterial to be considered a ‘versatile polymeric tool’ in the field of drug delivery. PGA and its variations can self-assemble into nanoparticles (NPs) and interact at different levels with small active molecules. PGA derivatives are usually obtained by functionalising the glyceryl side hydroxyl group present along the main polymer scaffold. However, if the synthetic pathways are not finely tuned, the self-assembling ability of these new polymeric modifications might be hampered by the poor amphiphilic balance. For this reason, we have designed a straightforward one-pot synthetic modification, using a small library of diols in combination with glycerol, aimed at altering the backbone of the polymer without affecting the hydrophilic glyceryl portion. The diols introduce additional functionality into the backbone of PGA alongside the secondary hydroxyl group already present. We have investigated how extra functionalities along the polymer backbone alter the final polymer reactivity as well the chemical and biological properties of the nanoparticles. In addition, with the intent to further improve the green credentials of the enzymatic synthesis, a solvent derived from renewable resources, (2-methyl tetrahydrofuran, 2-MeTHF) was employed for the synthesis of all the PGA-variants as a replacement for the more traditionally used and fossil-based tetrahydrofuran (THF). In vitro assays carried out to evaluate the potential of these novel materials for drug delivery applications demonstrated very low cytotoxicity characteristic against NIH 3T3 model cell line.

Original languageEnglish
Article number123912
JournalPolymer
Volume228
DOIs
Publication statusPublished - 16 Jul 2021
Externally publishedYes

Keywords

  • Enzymatic polymerisation
  • Polyglycerol adipate (PGA)
  • Self-assembly

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

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