Synthesis, characterization, thermokinetic analysis and biological application of novel allyl glucosamine based glycopolymers

Yeliz Yıldırım; Fatma Telli; Erkan Kahraman; John M Gardiner

doi:10.1080/15685551.2023.2199506

Synthesis, characterization, thermokinetic analysis and biological application of novel allyl glucosamine based glycopolymers

Des Monomers Polym. 2023 Apr 11;26(1):117-131. doi: 10.1080/15685551.2023.2199506. eCollection 2023.

Authors

Yeliz Yıldırım¹, Fatma Telli¹, Erkan Kahraman², John M Gardiner³

Affiliations

¹ Faculty of Science, Department of Chemistry, Ege University, Bornova, İzmir, Turkey.
² Atatürk Health Services Vocational School, Ege University, Bornova, İzmir, Turkey.
³ Department of Chemistry, School of Natural Science University of Manchester, Manchester, UK.

Abstract

The synthesis of glycopolymers by copolymerising an allyl glucosamine (AG) monomer with co-monomers methyl methacrylate (MMA), acrylonitrile (AN) and 2-hydroxyethyl methacrylate (HEMA) was investigated via free-radical polymerisation of 2,2-azobisisobutyronitrile (AIBN) in dimethylformamide (DMF). Three new copolymers, poly(AG-co-MMA), poly(AG-co-AN) and poly(AG-co-HEMA), were obtained. The chemical structures of the glycopolymers were analysed using ¹H-NMR, ¹³C-NMR and FTIR. The thermal properties and degradation kinetics of the three glycopolymers were examined by thermogravimetric (TG) analysis at different heating rates. The effects of different co-monomers on the copolymerisation yield, thermal properties and biological activities of the resulting glycopolymers were investigated. The activation energies of the decomposition stages were calculated using the Flynn-Wall-Ozawa (FWO) and Kissinger methods. Furthermore, the biological activity of AG monomers and glycopolymers was studied and compared to chitosan. Poly(AG-co-HEMA) had the most significant effect on MCF-7 cell viability, and all glycopolymers have a low toxic effect profile on MCF-7 cell lines.

Keywords: Glycopolymers; biological applications; carbohydrate-based allyl copolymer; decomposition kinetic; thermal analysis.