Chitosan impregnation with biologically active tryaryl imidazoles in supercritical carbon dioxide

J Mater Sci Mater Med. 2016 Sep;27(9):141. doi: 10.1007/s10856-016-5753-y. Epub 2016 Aug 18.

Abstract

The presented paper is focused on impregnation of chitosan and its derivatives with a biologically active triaryl imidazole model compound ((2-2-hydroxyphenyl)-4.5-diphenyl-1H-imidazole) in the supercritical carbon dioxide medium. Since initial chitosan represents a polycation-exchange resin and does not swell in supercritical carbon dioxide, the impregnation was carried out in the presence of water (0.15-3.0 vol%). The maximum 2-2-hydroxyphenyl)-4.5-diphenyl-1H-imidazole concentration in a chitosan film was achieved at the ~5 × 10(-3) g/cm(3) water content in the reactor. We also used hydroxy carboxylic acid derivatives of chitosan and its copolymer with polylactide as matrices for introduction of hydrophobic 2-2-hydroxyphenyl)-4.5-diphenyl-1H-imidazole. We have shown that unmodified chitosan contains the greatest amount of 2-2-hydroxyphenyl)-4.5-diphenyl-1H-imidazole, as compared with its hydrophobic derivatives. The kinetics of 2-2-hydroxyphenyl)-4.5-diphenyl-1H-imidazole diffusion from a chitosan matrix was studied in acidified water with pH 1.6. We found that the complete release of 2-2-hydroxyphenyl)-4.5-diphenyl-1H-imidazole into the aqueous phase from unmodified chitosan films occurred in 48 h, while its complete release from chitosan modified with hydroxy carboxylic acids occurred in 5 min or less.

MeSH terms

  • Biocompatible Materials / chemistry
  • Carbon Dioxide / chemistry*
  • Carboxylic Acids / chemistry
  • Cations
  • Chitosan / chemistry*
  • Diffusion
  • Drug Delivery Systems
  • Green Chemistry Technology
  • Hydrogen-Ion Concentration
  • Imidazoles / chemistry*
  • Kinetics
  • Luminescence
  • Polymers / chemistry
  • Pressure
  • Solvents / chemistry
  • Spectrophotometry, Ultraviolet
  • Temperature
  • Water / chemistry

Substances

  • Biocompatible Materials
  • Carboxylic Acids
  • Cations
  • Imidazoles
  • Polymers
  • Solvents
  • Water
  • Carbon Dioxide
  • Chitosan