Synthesis and Characterization of Isosorbide-Based Polyurethanes Exhibiting Low Cytotoxicity Towards HaCaT Human Skin Cells

对 HaCaT 人体皮肤细胞具有低细胞毒性的异山梨醇基聚氨酯的合成与表征

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作者:Barbara S Gregorí Valdés, Clara S B Gomes, Pedro T Gomes, José R Ascenso, Hermínio P Diogo, Lídia M Gonçalves, Rui Galhano Dos Santos, Helena M Ribeiro, João C Bordado

Abstract

The synthesis of four samples of new polyurethanes was evaluated by changing the ratio of the diol monomers used, poly(propylene glycol) (PPG) and D-isosorbide, in the presence of aliphatic isocyanates such as the isophorone diisocyanate (IPDI) and 4,4'-methylenebis(cyclohexyl isocyanate) (HMDI). The thermal properties of the four polymers obtained were determined by DSC, exhibiting Tg values in the range 55⁻70 °C, and their molecular structure characterized by FTIR, ¹H, and 13C NMR spectroscopies. The diffusion coefficients of these polymers in solution were measured by the Pulse Gradient Spin Echo (PGSE) NMR method, enabling the calculation of the corresponding hydrodynamic radii in diluted solution (1.62⁻2.65 nm). The molecular weights were determined by GPC/SEC and compared with the values determined by a quantitative 13C NMR analysis. Finally, the biocompatibility of the polyurethanes was assessed using the HaCaT keratinocyte cell line by the MTT reduction assay method showing values superior to 70% cell viability.

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