Succinylation of Polyallylamine: Influence on Biological Efficacy and the Formation of Electrospun Fibers.

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

doi:10.3390/polym13172840

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.

Highlights

Polyallylamine hydrochloride (PAA) is a synthetic polyelectrolyte obtained by polymerization of allylamine
This work investigates the succinylation of primary amines of the synthetic polyelectrolyte polyallylamine (PAA)
Interest persists in finding suitable antimicrobial agents against the growth of Pseudomonas aeruginosa and Staphylococcus aureus which are frequently found on human skin but can become potentially pathogenic [9]

Summary

Introduction

Polyallylamine hydrochloride (PAA) is a synthetic polyelectrolyte obtained by polymerization of allylamine. It has been previously used for the production of nanoparticles [1], for polyelectrolyte multilayers [2], for purification of water [3], as an ion exchanger [4], or for the removal or absorbance of heavy and rare metals [5]. Succinylated materials could be used for the production of antimicrobial wound dressings [21]. The succinylation of PAA and its influence on the biocompatibility in a mouse fibroblast model system (L929 cells) and the antimicrobial efficacy against S. aureus and P. aeruginosa were investigated. The influence of the spinning parameters and polyampholyte on the fiber diameter was assessed

Methods

Results

Conclusion