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

作者: Robert Kaplánek , Oldřich Paleta , Ivana Ferjentsiková , Milan Kodíček

DOI: 10.1016/J.JFLUCHEM.2008.12.001

关键词:

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

参考文章(60)
Claude Selve, Bertrand Castro, Patrick Leempoel, Gérard Mathis, Thierry Gartiser, Jean-J. Delpuech, Synthesis of homogeneous polyoxyethylene perfluorcalkyl surfactants Tetrahedron. ,vol. 39, pp. 1313- 1316 ,(1983) , 10.1016/S0040-4020(01)91897-6
Robert Filler, Lev M. Yagupolskii, Yoshiro Kobayashi, Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications ,(1993)
Jean G. Riess, Simonne Pace, Leila Zarif, Highly effective surfactants with low hemolytic activity Advanced Materials. ,vol. 3, pp. 249- 251 ,(1991) , 10.1002/ADMA.19910030507
Katsuki Takai, Toshiyuki Takagi, Teruhiko Baba, Toshiyuki Kanamori, Highly fluorinated C18 fatty acids: synthesis and interfacial properties Journal of Fluorine Chemistry. ,vol. 125, pp. 1959- 1964 ,(2004) , 10.1016/J.JFLUCHEM.2004.09.017
Vladimı́r Cı́rkva, Bruno Améduri, Bernard Boutevin, Oldřich Paleta, None, CHEMISTRY OF (PERFLUOROALKYL)METHYL OXIRANES. REGIOSELECTIVITY OF RING OPENING WITH O-NUCLEOPHILES AND THE PREPARATION OF AMPHIPHILIC MONOMERS Journal of Fluorine Chemistry. ,vol. 84, pp. 53- 61 ,(1997) , 10.1016/S0022-1139(97)00032-8
F. Szönyi, A. Cambon, Synthesis de tensioactifs F-alkyles non ioniques monodisperses Journal of Fluorine Chemistry. ,vol. 36, pp. 195- 209 ,(1987) , 10.1016/S0022-1139(00)81027-1
Philippe Barthélémy, Nicolas Cuvillier, Yann Chaudier, Jean-Jacques Benattar, Bernard Pucci, Stability of Newton black films of highly fluorinated non-ionic surfactants Journal of Fluorine Chemistry. ,vol. 105, pp. 95- 102 ,(2000) , 10.1016/S0022-1139(00)00281-5
M. Gaysinski, J.P. Le Forestier, A. Cambon, J.M. Devoiselle, H. Maillols, P. Chang, Vésicules de tensioactifs bicaténaires mixtes: caractérisation et stabilité de ces systèmes moléculaires organisés Journal of Fluorine Chemistry. ,vol. 83, pp. 175- 182 ,(1997) , 10.1016/S0022-1139(97)00015-8
Oldřich Paleta, Ivona Dlouhá, Robert Kaplánek, Karel Kefurt, Milan Kodı́ček, Novel amphiphilic fluoroalkylated derivatives of xylitol, D-glucose and D-galactose for medical applications: hemocompatibility and co-emulsifying properties. Carbohydrate Research. ,vol. 337, pp. 2411- 2418 ,(2002) , 10.1016/S0008-6215(02)00287-2