Redox-responsive solid lipid microparticles composed of octadecyl acrylate and allyl disulfide

J Biomater Sci Polym Ed. 2018 Apr;29(5):476-490. doi: 10.1080/09205063.2017.1422854. Epub 2018 Jan 8.

Abstract

Redox-responsive solid lipid microparticles were prepared by an emulsification photo-polymerization method. Octadecyl acrylate (ODA) and a cross-linker (i.e. allyl disulfide (ADS) and octadiene (ODE)) were dissolved in dichloromethane, it was emulsified in poly(vinyl alcohol) solution, and the resulting O/W emulsion was irradiated with UV light. On the scanning electron microscope micrographs, the microparticles were sphere-like and they were not markedly different from the oil droplets in size. Using the atomic compositions analyzed by energy dispersive X-ray spectroscopy, the ODA to cross-linker molar ratio of ODA/ADS microparticles and ODA/ODE ones were calculated to be 1:0.13 and 1:0.15, respectively. In the FT-IR spectra of the microparticles, the signal of the vinyl group was hardly detected, implying that the monomer and the cross-linkers participated in the photo-polymerization. In differential scanning calorimetry study, ODA/ADS microparticles and ODA/ODE ones exhibited their endothermic peaks around 42.9 and 41.3 °C, respectively, possibly due to the melting of polymeric ODA. Dithiothreitol (DTT, a reducing agent) concentration had little effect on the release degree of dye loaded in ODA/ODE microparticles. Whereas, DTT concentration had a significant effect on the release degree of dye loaded in ODA/ADS microparticles. The release degree at 26 °C was weakly affected by DTT concentration. When the temperature was 37 °C, DTT concentration had a strong effect on the release degree. The disulfide cross-linker (i.e. ADS) can be broken to thiol compounds by the reducing agent, resulting in an increase in the release degree.

Keywords: Solid lipid microparticles; allyl disulfide; emulsification photo-polymerization; octadecyl acrylate; reduction-responsive release.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylates / chemistry*
  • Allyl Compounds / chemistry*
  • Disulfides / chemistry*
  • Drug Carriers / chemistry*
  • Lipids / chemistry*
  • Microspheres*
  • Oxidation-Reduction

Substances

  • Acrylates
  • Allyl Compounds
  • Disulfides
  • Drug Carriers
  • Lipids
  • diallyl disulfide