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

摘要

Two series of novel perfluoroalkylated amphiphilic compounds were synthesized from monomethyl ethers of mono-,di-and tri-(oxyethylene)glycols.The first series CH3(OCH2CH2)_nOCH2CH(OH)CH2-CF2(CF2CF2)nCF3(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-(perfluoroalk-ylmethyl)oxiranes in 76-97% yields.The second series CH3(OCH2CH2)_nOCH2CH2CH2-CF2(CF2CF2)_nCF3(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.