Novel perfluoroalkylated oligo(oxyethylene) methyl ethers with high hemocompatibility and excellent co-emulsifying properties for potential biomedical uses |
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Authors: | Robert Kaplánek Ivana Ferjentsiková |
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Institution: | a Department of Organic Chemistry, Prague Institute of Chemical Technology, Technická 5, 16628 Prague 6, Czech Republic b Department of Biochemistry and Microbiology, Prague Institute of Chemical Technology, Technická 5, 16628 Prague 6, Czech Republic |
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Abstract: | 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-(perfluoroalkylmethyl)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. |
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Keywords: | Perfluoroalkylated oligo(oxyethylene) ethers Perfluoroalkylated oxiranes Radical addition Reduction of C-I bond d-xylitol" target="_blank">1-O-Fluoroalkyl-d-xylitol Hemocompatibility Microemulsion stability |
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