Les cyclodextrines amphiphiles et leurs applications. Élaboration de nanoparticules de cyclodextrines amphiphiles pour des applications biomédicales

Kawabata, 1986, Formation and deposition of monolayers of amphiphilic β-cyclodextrin derivatives, Chem Lett, 11, 1933, 10.1246/cl.1986.1933 Ling, 1993, Cyclodextrin liquid crystals: synthesis and self-organisation of amphiphilic thio-β-cyclodextrins, Chem Commun, 438, 10.1039/C39930000438 Gadelle, 1991, Selective halogenation of cyclic maltose oligosaccharides in the C-6 position and synthesis of per(3,6-anhydro) cyclic maltose oligosaccharides, Angew Chem Int Ed Engl, 30, 78, 10.1002/anie.199100781 Gallois-Montbrun, 2007, Direct synthesis of novel amphiphilic cyclodextrin, J Incl Phenom Macrocycl Chem, 57, 131, 10.1007/s10847-006-9208-9 Memisoglu, 2002, Intravitreal delivery of oligonucleotides by sterically stabilized liposomes, J Pharm Sci, 91, 1214 Zhang, 1991, Formation of amphiphilic cyclodextrins via hydrophobic esterification at the secondary hydroxyl face, Tetrahedron Lett, 32, 2769, 10.1016/0040-4039(91)85081-F Lesieur, 2000, Phase behavior of fully hydrated DMPC-amphiphilic cyclodextrin systems, Chem Phys Lipids, 106, 127, 10.1016/S0009-3084(00)00149-3 Khan, 1998, Methods for selective modifications of cyclodextrins, Chem Rev, 98, 1977, 10.1021/cr970012b Canceill, 1992, Channel-type molecular structures. Part 2. Synthesis of bouquet-shaped molecules based on a β-cyclodextrin core, Helv Chim Acta, 75, 791, 10.1002/hlca.19920750315 Wenz, 1991, Synthesis and characterization of some lipophilic per(2,6-di-O-alkyl)cyclomaltooligosaccharides, Carbohydr Res, 214, 257, 10.1016/0008-6215(91)80033-J Falvey, 2005, Bilayer vesicles of amphiphilic cyclodextrins: host membranes that recognize guest molecules, Chem Eur J, 11, 1171, 10.1002/chem.200400905 Salameh, 2005, Synthesis and interfacial properties of amphiphilic β-cyclodextrins and their substitution at the O-6 position with a mono bio-recognizable galactosyl antenna, Tetrahedron, 61, 8740, 10.1016/j.tet.2005.06.054 Donohue, 2002, Cationic β-cyclodextrin bilayer vesicles, Chem Commun, 23, 2864, 10.1039/B207238F Diaz-Moscoso, 2008, Rational design of cationic cyclooligosaccharides as efficient gene delivery systems, Chem Commun, 17, 2001, 10.1039/b718672j Leydet, 1998, Polyanion inhibitors of HIV and other viruses, 7. Polyanionic compounds and polyzwitterionic compounds derived from cyclodextrins as inhibitors of HIV transmission, J Med Chem, 41, 4927, 10.1021/jm970661f Kraus, 2001, General approach to the synthesis of persubstituted hydrophilic and amphiphilic β-cyclodextrin derivatives, J Org Chem, 66, 4595, 10.1021/jo010046q Sallas, 2008, Amphiphilic cyclodextrins – advances in synthesis and supramolecular chemistry, Eur J Org Chem, 6, 957, 10.1002/ejoc.200700933 Uekama, 1998, Cyclodextrin Drug Carrier Systems, Chem Rev, 98, 2045, 10.1021/cr970025p Folkman, 1998, Control of angiogenesis with synthetic heparin substitutes, Science, 243, 1490, 10.1126/science.2467380 Otake, 1994, Modified cyclodextrin sulfates (mCDS11) have potent inhibitory activity against HIV and high oral bioavailability, Antiviral Chem Chemother, 5, 155, 10.1177/095632029400500303 Shing, 1990, Affinity of fibroblast growth factors for β-cyclodextrin tetradecasulfate, Anal Biochem, 185, 108, 10.1016/0003-2697(90)90263-9 Weisz, 1997, A basic compositional requirement of agents having heparin-like cell-modulating activities, Biochem Pharmacol, 54, 149, 10.1016/S0006-2952(97)00157-3 Dubes, 2001, An efficient regio-specific synthetic route to multiply substituted acyl-sulfated β-cyclodextrins, Tetrahedron Lett, 42, 9147, 10.1016/S0040-4039(01)01992-X Dubes, 2003, Synthesis and characterization of sulfated amphiphilic α-,β- and gamma. -cyclodextrins: application to the complexation of acyclovir, Carbohydr Res, 338, 2185, 10.1016/S0008-6215(03)00356-2 Abdelwahed, 2008, Sulfated and non-sulfated amphiphilic-β-cyclodextrins: Impact of their structural properties on the physicochemical properties of nanoparticles, Int J Pharm, 351, 289, 10.1016/j.ijpharm.2007.09.035 Sukegawa, 2002, Erythrocyte-like liposomes prepared by means of amphiphilic cyclodextrin sulfates, Chem Commun, 5, 430, 10.1039/b110673b Fessi H, Puisieux F, Devissaguet JP, Thies C. Process for the preparation of dispersible colloidal systems of a substance in the form of nanoparticles, US Patent US5118528, 1988. Dubes, 2003, Scanning electron microscopy and atomic force microscopy imaging of solid lipid nanoparticles derived from amphiphilic cyclodextrins, Eur J Pharm Biopharm, 55, 279, 10.1016/S0939-6411(03)00020-1 Von Plessing Rossel, 2000, Inclusion complex of the antiviral drug acyclovir with cyclodextrin in aqueous solution and in solid phase, Quimica Nova, 23, 749, 10.1590/S0100-40422000000600007 Ravey, 1994, Properties of fluorinated non-ionic surfactant-based systems and comparison with non-fluorinated systems, Colloids Surfaces A, 84, 11, 10.1016/0927-7757(93)02731-S Braun, 1985, Porcine-pancreatic α amylase hydrolysis of substrates containing 6-deoxy-D-glucose and 6-deoxy-6-fluoro-D-glucose and the specificity of subsite binding, Carbohydr Res, 143, 107, 10.1016/S0008-6215(00)90700-6 Diakur, 1999, Synthesis and drug complexation studies with β-cyclodextrins fluorinated on the primary face, J Carbohydr Chem, 18, 209, 10.1080/07328309908543991 Skiba, 2003, Design of nanocapsules based on novel fluorophilic cyclodextrin derivatives and their potential role in oxygen delivery, J Incl Phenom Macrocycl Chem, 44, 151, 10.1023/A:1023090528809 Granger, 2000, Fluorine containing β-cyclodextrin: a new class of amphiphilic carriers, Tetrahedron Lett, 41, 9257, 10.1016/S0040-4039(00)01716-0 Peroche, 2002, Novel fluorinated amphiphilic cyclodextrin derivatives: Synthesis of mono-, di- and heptakis-(6-deoxy-6-perfluoroalkylthio)-β- cyclodextrins, Tetrahedron Lett, 44, 241, 10.1016/S0040-4039(02)02539-X Pearce, 2000, Diisobutylaluminum-promoted regioselective De-O-benzylation of perbenzylated cyclodextrins: a powerful new strategy for the preparation of selectively modified cyclodextrins, Angew Chem, Int Ed Engl, 39, 3610, 10.1002/1521-3773(20001016)39:20<3610::AID-ANIE3610>3.0.CO;2-V Peroche, 2005, Synthesis and characterization of novel nanospheres made from amphiphilic perfluoroalkylthio-β -cyclodextrins, Eur J Pharm Biopharm, 60, 123, 10.1016/j.ejpb.2005.01.005 Tchoreloff, 1995, Amphiphilic monolayers of insoluble cyclodextrins at the water/air interface. Surface Pressure and surface potential studies, Langmuir, 11, 191, 10.1021/la00001a033 Bertino-Ghera, 2007, Synthesis and characterization of O-6-alkylthio- and perfluoroalkylpropanethio-α-cyclodextrins and their O-2-,O-3-methylated analogues, New J Che, 31, 1899, 10.1039/b703894a Bertino-Ghera, 2008, Control of the Regioselectivity for New Fluorinated Amphiphilic Cyclodextrins: Synthesis of Di- and Tetra(6-deoxy-6-alkylthio)- and 6-(Perfluoroalkylpropanethio)-α-cyclodextrin Derivatives, J Org Chem, 73, 7317, 10.1021/jo801111b Memisoğlu, 2003, Hincal, Direct formation of nanospheres from amphiphilic β-cyclodextrin inclusion complexes, Arch Pharm Res, 20, 117, 10.1023/A:1022263111961