Novel nanoparticles made from amphiphilic perfluoroalkyl α-cyclodextrin derivatives: Preparation, characterization and application to the transport of acyclovir

International Journal of Pharmaceutics - Tập 375 - Trang 155-162 - 2009
Bernard Bertino Ghera1, Florent Perret1, Yves Chevalier2, Hélène Parrot-Lopez1
1ICBMS, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, LCO2-CSAp, 43 boulevard du 11 novembre 1918, Villeurbanne, F-69622, France; CNRS, UMR5246, Villeurbanne, F-69622, France; Université de Lyon, Lyon, F-69622, France; Université Lyon 1, Lyon, F-69622, France
2LAGEP, Laboratoire d’Automatiques et de Génie des Procédé, UMR-CNRS 5007, Bât. 308G ESCPE-Lyon, 43 Bd du 11 Novembre 1918, F-69622 Villeurbanne, Université de Lyon, Lyon, F-69622, France; Université Lyon 1, Lyon, F-69622, France

Tài liệu tham khảo

Bertino Ghera, 2007, Synthesis and characterisation of O-6-alkylthio- and perfluoroalkylpropanethio-α-cyclodextrins and their O-2-O-3-methylated analogues, New J. Chem., 31, 1899, 10.1039/b703894a Dubes, 2001, An efficient regio-specific synthetic route to multiply substituted acyl-sulphated β-cyclodextrins, Tetrahedron Lett., 42, 9147, 10.1016/S0040-4039(01)01992-X 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 Duchêne, 1999, Cyclodextrins in targeting: application to nanoparticles, Adv. Drug Deliv. Rev., 36, 29, 10.1016/S0169-409X(98)00053-2 Fessi, H., Puissieux, F., Devissaguet, J.-P., Thies, C., 1988. Process for the preparation of dispersible colloidal systems of a substance in the form of nanoparticles. US Patent US5118528, 1988, 2 June. Fresta, 1999, Characterization and in-vivo ocular absorption of liposome-encapsulated acyclovir, J. Pharm. Pharmacol., 51, 565, 10.1211/0022357991772664 Ganachaud, 2005, Nanoparticles and nanocapsules created using the Ouzo effect: spontaneous emulsification as an alternative to ultrasonic and high-shear devices, Chem. Phys. Chem., 6, 209, 10.1002/cphc.200400527 Granger, 2000, Fluorine containing β-cyclodextrin: a new class of amphiphilic carriers, Tetrahedron Lett., 41, 9257, 10.1016/S0040-4039(00)01716-0 Guittard, 2001, Highly fluorinated molecular organised systems: strategy and concept, J. Fluorine. Chem., 107, 363, 10.1016/S0022-1139(00)00380-8 Krafft, 2001, Fluorocarbons and fluorinated amphiphiles in drug delivery and biomedical research, Adv. Drug Deliv. Rev., 47, 209, 10.1016/S0169-409X(01)00107-7 Laskin, 1982, Pharmacokinetics and tolerance of acyclovir, a new anti-herpes virus agent, in humans, Antimicrob. Agents Chemother., 21, 393, 10.1128/AAC.21.3.393 Memisoğlu, 2003, Direct formation of nanospheres from amphiphilic β-cyclodextrin inclusion complexes, Pharm. Res., 20, 117, 10.1023/A:1022263111961 Peroche, 2003, 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 Peroche, 2005, Synthesis and characterisation of novel nanospheres made from amphiphilic perfluoroalkylthio-β-cyclodextrins, Eur. J. Pharm. Biopharm., 60, 123, 10.1016/j.ejpb.2005.01.005 Salas, 2008, Amphiphilic cyclodextrins–advances in synthesis and supramolecular chemistry, Eur. J. Org. Chem., 957, 10.1002/ejoc.200700933 Terry, N., Rival, D., Coleman, A.W., Perrier, E., 2001. Novel non-hydroxyalkylated cyclodextrin derivatives and their use in the transport of active ingredients across skin tissue. GB Patent GB2232102, 14 Nov. Tchoreloff, 1995, Amphiphilic monolayers of insoluble cyclodextrins at the water/air interface. surface pressure and surface potential studies, Langmuir, 11, 191, 10.1021/la00001a033 Uekama, 1998, Cyclodextrins drug carrier systems, Chem. Rev., 98, 2045, 10.1021/cr970025p Vitale, 2003, Liquid droplet dispersions formed by homogeneous liquid-liquid nucleation: the ouzo effect, Langmuir, 19, 4105, 10.1021/la026842o Von Plessing Rossel, 2000, Inclusion complex of the antiviral drug acyclovir with cyclodextrin in aqueous solution and in solid phase, Quim. Nova, 23, 749, 10.1590/S0100-40422000000600007 Wouessidjewe, 1996, A new concept in drug delivery based on skirt-shaped cyclodextrin aggregates, present state and future prospects, STP Pharma. Sciences, 6, 21