Phosphonic acid-functionalized poly(amido amine) macromers for biomedical applications

Novel phosphonic acid-functionalized poly(amido amine) (PAA) macromers are synthesized through aza-Michael addition of 2-aminoethyl phosphonic acid or its mixture with 5-amino-1-pentanol at different ratios onto N,N'-methylene bis(acrylamide) to control the amount of phosphonic acid functionality. The macromers were homo- and copolymerized with 2-hydroxyethyl methacrylate at different ratios to obtain hydrogels with various hydrophilicities. The hydrogels' swelling, biodegradation and mineralization properties were evaluated. The swelling and degradation rates of the gels can be tuned by the chemical structure of PAA macromer precursors as well as pH and CaCl₂ pre-treatment. The hydrogels show composition-dependent mineralization in SBF and 5xSBF, as evidenced from Fourier transform infrared spectroscopy (FTIR), and scanning electron microscopy/energy dispersive X-ray spectroscopy (SEM/EDX) analyses. The degradation products of the hydrogels have no effect on U-2 OS, Saos-2 and NIH 3T3 cells, suggesting their cytocompatibility. Overall, these materials have potential to be used as nontoxic degradable biomaterials.