Water-soluble PEG segmented mannose-based macromolecules: Synthesis, characterization and their biocompatibility

Abstract

The macromolecular architectures, namely mannose-based methacrylate acetyl-mannopyranoside and PEG block copolymers [AB type copolymer [PEG-b-PMAM], poly(ethyleneglycol)-b-poly(methacryl-2,3,4,6-tetra-O-acetyl-D-mannopyranoside) and ABA type copolymer [PMAM-b-PEG-b-PMAM], poly(methacryl-2,3,4,6-tetra-O-acetyl-D-mannopyranoside)-b-poly(ethyleneglycol)-b-poly(methacryl-2,3,4,6-tetra-O-acetyl-D-mannopyranoside)] were synthesized by atom transfer radical polymerization (ATRP) method that were deacetylated to generate the corresponding water-soluble and biocompatible glycopolymer macromolecules. The molecular weight of acetyl and deacetylate macromolecules was in the range of 7083-9499 and 4659-6026, as determined by GPC and proton NMR spectra. The 5 % decomposition temperatures for acetylated methacrylate macromolecules (218-299 °C) were higher than the corresponding water-soluble macromolecules (204-248 °C). The conjugation of poly(methacryl-2,3,4,6-tetra-O-acetyl-D-mannopyranoside) (PMAM) segment with the PEG block decreased the glass transition (T_g) value, and the water-soluble macromolecules displayed T_g in the range of 92-95 °C. The biocompatibility of the synthesized water-soluble mannose-based macromolecules was determined using Human Bone Derived Cells (HBDC) culture with the TCP (Tissue culture plastic) template as control. Using three different concentrations of the synthesized glycopolymers, HBDC's were cultured for 1, 3, and 7 days. The effect of mannomethacrylate macromolecules on mitochondrial activity of HBDC's was estimated using colorimetry that showed the conversion of MTS [3-(4,5-dimethyl-thiazol-2-yl)-2,5-diphenyl-tetrazolium-bromide] to formazan (MTS assay). ABA type diblock copolymer architecture exhibited increased absorbance values of 3 and 7 day cultures at 1-100 M concentrations, with the highest values observed at a concentration of 1 M for day 3 cultures. The design of these novel mannose-based macromolecules is important for improving cell proliferation, cell adhesion, and osteointegration efficiency.

Keywords: ATRP; Biological macromolecules; Biomedical applications; Cell proliferation; Human bone derived cells; Macromolecules from renewable resources; Mannose polymers; Structure-properties.