Succinylation of polyallylamine: Influence on biological efficacy and the formation of electrospun fibers

Lucija Jurko, Matej Bračič, Silvo Hribernik, Damjan Makuc, Janez Plavec, Filip Jerenec, Sonja Žabkar, Nenad Gubeljak, Alja Štern, Rupert Kargl*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Succinylation of proteins is a commonly encountered reaction in biology and introduces negatively charged carboxylates on previously basic primary amine groups of amino acid residues. In analogy, this work investigates the succinylation of primary amines of the synthetic polyelectrolyte polyallylamine (PAA). It investigates the influence of the degree of succinylation on the cytotoxicity and antibacterial activity of the resulting polymers. Succinylation was performed in water with varying amounts of succinic anhydride and at different pH values. The PAA derivatives were analyzed in detail with respect to molecular structure using nuclear magnetic resonance and infrared absorbance spectroscopy. Polyelectrolyte and potentiometric charge titrations were used to elucidate charge ratios between primary amines and carboxylates in the polymers. The obtained materials were then evaluated with respect to their minimum inhibitory concentration against Staphylococcus aureus and Pseudomonas aeruginosa. The biocompatibility was assessed using mouse L929 fibroblasts. The degree of succinylation decreased cytotoxicity but more significantly reduced antibacterial efficacy, demonstrating the sensitivity of the fibroblast cells against this type of ampholytic polyelectrolytes. The obtained polymers were finally electrospun into microfiber webs in combination with neutral water-soluble polyvinyl alcohol. The resulting non-woven could have the potential to be used as wound dressing materials or coatings.

Original languageEnglish
Article number2840
JournalPolymers
Volume13
Issue number17
DOIs
Publication statusPublished - 1 Sep 2021

Keywords

  • Antimicrobial effect
  • Aqueous chemistry
  • Cytotoxicity
  • Electrospinning
  • Nanofibers: mouse L929 fibroblasts
  • Polyallylamine hydrochloride
  • Pseudomonas aeruginosa
  • Staphylococcus aureus
  • Succinylation

ASJC Scopus subject areas

  • Chemistry(all)
  • Polymers and Plastics

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