Carboxymethylpullulan Grafted with Aminoguaiacol: Synthesis, Characterization, and Assessment of Antibacterial and Antioxidant Properties

Biomacromolecules. 2017 Oct 9;18(10):3238-3251. doi: 10.1021/acs.biomac.7b00899. Epub 2017 Sep 1.

Abstract

Aminoguaiacol, the aminated derivative of guaiacol, a natural phenolic compound, was chemically grafted onto a polysaccharide (carboxymethylpullulan, CMP) in the presence of the activator agent 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride (EDCI). The grafted polysaccharides were characterized by FTIR and 1H NMR spectroscopy to confirm and quantify the grafting. All polysaccharide derivatives (grafting rates of aminoguaiacol between 16% and 58%) were soluble in water. Their physicochemical properties were studied in a dilute regime and a semidilute regime by light scattering, fluorescence, and rheology, showing associative properties with peculiar polysoap behavior. The antibacterial activities of the synthesized products against Staphyloccocus aureus were assessed using a counting method. The antioxidant activities of the derivatives were also highlighted using the α,α-diphenyl-β-picrylhydrazyl (DPPH) method. Finally, the cytotoxicity of the derivatives was studied with fibroblast cells and they showed a very good cytocompatibility. Such polymers could be used to replace chemical preservatives in food and cosmetic aqueous formulations.

MeSH terms

  • Amines / chemistry
  • Animals
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Cell Line
  • Cell Survival / drug effects
  • Glucans / chemistry*
  • Guaiacol / analogs & derivatives*
  • Mice
  • Staphylococcus aureus / drug effects

Substances

  • Amines
  • Anti-Bacterial Agents
  • Antioxidants
  • Glucans
  • carboxymethylpullulan
  • Guaiacol