Synthesis and hemocompatibility of biomembrane mimicing poly(carbonate urethane)s containing fluorinated alkyl phosphatidylcholine side groups.

In this article, we designed and synthesized biomembrane mimicing segmented poly(carbonate urethane)s containing fluorinated alkyl phosphatidylcholine (PC) side groups. To obtain these novel poly(carbonate urethane)s, a new diol with a long side chain fluorinated alkyl phosphatidylcholine polar headgroup (2-[2-2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-10-ethoxy-decyloxy-N-(2-hydroxy-1-hydroxymethyl-1-methyl-ethyl)-acetamide] phosphatidylcholine, HFDAPC) was first synthesized and characterized. Then a series of poly(carbonate urethane)s containing fluorinated alkyl phosphatidylcholine side groups were synthesized using methylenebis(phenylene isocyanate) (MDI), poly(1,6-hexyl-1,5-pentyl carbonate) diol (PHPCD), 1,4-butandiol (BDO), and HFDAPC. The obtained fluorinated phosphatidylcholine poly(carbonate urethane)s (FPCPCU) possessed high molecular weight, narrower molecular weight distribution, and good mechanical properties as characterized by GPC and Instron, showing an increased hydrophilicity and a possible arrangement of surface structure as characterized by water contact angle. XPS results indicated that the phosphatidylcholine polar headgroups have been indeed pulled out to the surface with the help of the migration of the fluorinated side chain that was directly connected with the phosphatidylcholine polar headgroup. A preliminary result by protein adsorption and platelet adhesion experiments suggested that only 5 approximately 12.5 mol % phosphatidylcholine could be enough for good hemocompatibility. The current work demonstrates a new synthetic approach that can be used to bring the bioactive PC groups to the surface of the PC-containing polyurethanes more effectively.