Effect of the rigid segment content on the properties of segmented polyurethanes conjugated with atorvastatin as chain extender

J Mater Sci Mater Med. 2018 Oct 24;29(11):161. doi: 10.1007/s10856-018-6165-y.

Abstract

Segmented polyurethanes were prepared with polycaprolactone diol as soft segment and various amounts of 4,4´-Methylenebis(cyclohexyl isocyanate) and atorvastatin, a statin used for lowering cholesterol, in order to obtain SPU with different content of rigid segments. Polyurethanes with 35% or 50% of rigid segment content were physicochemically characterized and their biocompatibility assessed with L929 fibroblasts. High concentrations of atorvastatin were incorporated by increasing the content of rigid segments as shown by FTIR, Raman, NMR, XPS and EDX. Thermal and mechanical characterization showed that polyurethanes containing atorvastatin and 35% of rigid segments were low modulus (13 MPa) semicrystalline polymers as they exhibited a glass transition temperature (Tg) at -38 °C, melting temperature (Tm) at 46 °C and crystallinity close to 35.9% as determined by DSC. In agreement with this, X-ray diffraction showed reflections at 21.3° and 23.6° for PCL without reflections for atorvastatin suggesting its presence in amorphous form with higher potential bioavailability. Low content of rigid segments led to highly degradable polymer in acidic, alkaline and oxidative media with an acceptable fibroblast cytotoxicity up to 7 days possibly due to low atorvastatin content.

MeSH terms

  • Animals
  • Atorvastatin / chemistry*
  • Atorvastatin / toxicity
  • Biocompatible Materials / chemistry*
  • Biocompatible Materials / toxicity
  • Cell Line
  • Cell Survival / drug effects
  • Cyanates / chemistry*
  • Mice
  • Molecular Structure
  • Nonlinear Optical Microscopy
  • Polyesters / chemistry*
  • Polyesters / toxicity
  • Polyurethanes / chemistry*
  • Polyurethanes / toxicity
  • Spectrophotometry, Infrared
  • Temperature

Substances

  • Biocompatible Materials
  • Cyanates
  • Polyesters
  • Polyurethanes
  • polycaprolactone
  • methylene bis(4-cyclohexylisocyanate)
  • Atorvastatin