Novel injectable biomaterials for bone augmentation based on isosorbide dimethacrylic monomers

• Synthesis and characterization of novel dimethacrylic monomers based on isosorbide.
• Improved biocompatibility and hydrophilic nature of novel dimethacrylates.
• Shear-thinning behavior of compositions for improved rheological properties.

Drawbacks with the commonly used PMMA-based bone cements, such as an excessive elastic modulus and potentially toxic residual monomer content, motivate the development of alternative cements. In this work an attempt to prepare an injectable biomaterial based on isosorbide-alicyclic diol derived from renewable resources was presented. Two novel dimethacrylic monomers ISDGMA — 2,5-bis(2-hydroxy-3-methacryloyloxypropoxy)-1,4:3,6-dianhydro-sorbitol and ISETDMA — dimethacrylate of ethoxylated isosorbide were synthesized and used to prepare a series of low-viscosity compositions comprising bioactive nano-sized hydroxyapatite in the form of a two-paste system. Formulations exhibited a non-Newtonian shear-thinning behavior, setting times between 2.6 min and 5.3 min at 37 °C and maximum curing temperatures of 65 °C. Due to the hydrophilic nature of ISDGMA, cured compositions could absorb up to 13.6% water and as a result the Young's modulus decreased from 1429 MPa down to 470 MPa. Both, poly(ISDGMA) and poly(ISETDMA) were subjected to a MTT study on mice fibroblasts (BALB/3T3) and gave relative cell viabilities above 70% of control. A selected model bone cement was additionally investigated using human osteosarcoma cells (SaOS-2) in an MTS test, which exhibited concentration-dependent cell viability. The preliminary results, presented in this work reveal the potential of two novel dimethacrylic monomers in the preparation of an injectable biomaterial for bone augmentation, which could overcome some of the drawbacks typical for conventional acrylic bone cement.