Novel perfluoroalkylated oligo(oxyethylene) methyl ethers with high hemocompatibility and excellent co-emulsifying properties for potential biomedical uses

Abstract

Two series of novel perfluoroalkylated amphiphilic compounds were synthesized from monomethyl ethers of mono-, di- and tri-(oxyethylene) glycols. The first series CH 3(OCH 2CH 2) n OCH 2CH(OH)CH 2–CF 2(CF 2CF 2) n CF 3 ( n = 1–3) bearing the hydroxy group at the spacer between hydrophilic and hydrophobic parts was prepared by the reactions of the monomethyl ethers with 2-(perfluoroalkylmethyl)oxiranes in 76–97% yields. The second series CH 3(OCH 2CH 2) n OCH 2CH 2CH 2–CF 2(CF 2CF 2) n CF 3 ( n = 1–3) possessing the non-hydroxylated spacer was synthesized from allyl methyl ethers of oligo(oxyethylene) glycols using radical additions of perfluoroalkyl iodides and subsequent selective reductions of the C–I bond in the adducts in overall yields of 23–69%. Some of the novel amphiphilic compounds displayed very low hemolytic activity to erythrocytes and excellent co-emulsifying properties on testing on perfluorodecalin/Pluronic F-68 microemulsions. 1- O-(2-Hydroxy-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl)- d-xylitol was prepared by a novelized synthesis and employed as a standard compound in the testing.