Poly(N-isopropylacrylamide)/galactomannan from Delonix regia seed thermal responsive graft copolymer via Schiff base reaction

Int J Biol Macromol. 2021 Jan 1:166:144-154. doi: 10.1016/j.ijbiomac.2020.10.121. Epub 2020 Oct 22.

Abstract

Aminated poly(N-isopropylacrylamide) (PNIPAm-NH2) was grafted onto oxidized galactomannan polysaccharide extracted from Delonix regia (OXGM) via Schiff base reaction by a simple, rapid synthetic route, deprived of the use of organic solvents. Grafting was confirmed by FTIR and 1H NMR and the self-organizing ability of the obtained nanoparticle copolymers was investigated by dynamic light scattering (DLS). The minimum concentration required for self-organization (CAC) at 25 °C was higher than at 50 °C. Lower critical solution temperature (LCST) was in the range 34-40 °C, depending on both inserted PNIPAm-NH2 molar mass and on the presence of reduced imine bond. Synthesized copolymers are promising candidates for drug delivery as they show good cell viability, particle size around 250 nm and transition temperature closer to that of human body. Reaction success points out to the possibility of use free aldehyde groups of oxidized polysaccharide, not used in the copolymerization, to form a pro-drug with substances that possess NH2 groups in their structure, such as doxorubicin.

Keywords: Copolymer; Galactomannan; Nanoparticle; Poly(N-isopropylacrylamide); Schiff base.

MeSH terms

  • Acrylic Resins / chemistry*
  • Biocompatible Materials / chemical synthesis*
  • Fabaceae / chemistry*
  • Galactose / analogs & derivatives
  • Mannans / chemistry*
  • Polymerization
  • Schiff Bases / chemistry
  • Seeds / chemistry
  • Transition Temperature

Substances

  • Acrylic Resins
  • Biocompatible Materials
  • Mannans
  • Schiff Bases
  • galactomannan
  • poly-N-isopropylacrylamide
  • Galactose