TY - JOUR
T1 - Succinylation of polyallylamine: Influence on biological efficacy and the formation of electrospun fibers
AU - Jurko, Lucija
AU - Bračič, Matej
AU - Hribernik, Silvo
AU - Makuc, Damjan
AU - Plavec, Janez
AU - Jerenec, Filip
AU - Žabkar, Sonja
AU - Gubeljak, Nenad
AU - Štern, Alja
AU - Kargl, Rupert
PY - 2021/9/1
Y1 - 2021/9/1
N2 - 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.
AB - 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.
KW - Antimicrobial effect
KW - Aqueous chemistry
KW - Cytotoxicity
KW - Electrospinning
KW - Nanofibers: mouse L929 fibroblasts
KW - Polyallylamine hydrochloride
KW - Pseudomonas aeruginosa
KW - Staphylococcus aureus
KW - Succinylation
KW - polyallylamine hydrochloride
KW - succinylation
KW - aqueous chemistry
KW - cytotoxicity
KW - antimicrobial effect
KW - electrospinning
KW - nanofibers: mouse L929 fibroblasts
KW - Staphylococcus aureus
KW - Pseudomonas aeruginosa
UR - http://www.scopus.com/inward/record.url?scp=85113942936&partnerID=8YFLogxK
U2 - 10.3390/polym13172840
DO - 10.3390/polym13172840
M3 - Article
AN - SCOPUS:85113942936
SN - 2073-4360
VL - 13
JO - Polymers
JF - Polymers
IS - 17
M1 - 2840
ER -