Iminoboronate-chitooligosaccharides hydrogels with strong antimicrobial activity for biomedical applications

Carbohydr Polym. 2022 Jan 15:276:118727. doi: 10.1016/j.carbpol.2021.118727. Epub 2021 Oct 9.

Abstract

The paper reports hydrogels prepared from chitooligosaccharides with different polymerization degrees (14 to 51), by crosslinking with 2-formylphenylboronicacid in three molar ratios of their functionalities. The structural, morphological and supramolecular characterization confirmed a hydrogelation mechanism based on self-assembling of newly formed imine units and porous morphology. Rheological measurements confirmed the formation of thixotropic hydrogels, and swelling tests indicated mass equilibrium swelling values up to 25 in water and 9 in phosphate buffer saline. The monitoring of enzymatic degradability demonstrated the enhancing of biodegradation rate as long as the polymerization degrees of the oligomers decreased, the mass loss increasing from 16% to 43%. In vivo and ex-vivo biocompatibility investigation on experimental mice showed no cytotoxic effect, and in vitro antimicrobial tests revealed remarkable antimicrobial properties on nine strains, with a maximum inhibition diameter of 49 mm on Aspergilius brasiliensis and very good results on Cladosporium cladosporioides, Penicillium crysogenum and different Candida species.

Keywords: 2-Formylphenylboronic acid; Antimicrobial; Bioapplications; Chitooligosaccharides.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Bacteria / drug effects
  • Benzaldehydes / chemistry*
  • Benzaldehydes / pharmacology
  • Boronic Acids / chemistry*
  • Boronic Acids / pharmacology
  • Chitosan / chemistry*
  • Chitosan / pharmacology
  • Cross-Linking Reagents / chemistry
  • Fungi / drug effects
  • Hydrogels / chemistry*
  • Imines / chemistry
  • Mice
  • Molecular Structure
  • Oligosaccharides / chemistry*
  • Oligosaccharides / pharmacology
  • Porosity
  • Rheology / methods
  • Spectroscopy, Fourier Transform Infrared / methods

Substances

  • 2-formylphenylboronic acid
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Benzaldehydes
  • Boronic Acids
  • Cross-Linking Reagents
  • Hydrogels
  • Imines
  • Oligosaccharides
  • oligochitosan
  • Chitosan