Pharmaceutical use of cyclodextrines: Perspectives for drug targeting and control of membrane interactions;Les cyclodextrines en pharmacie: Perspectives pour le ciblage d'actifs thérapeutiques et le contrôle d'interactions membranaires

Annales Pharmaceutiques Francaises

Volumn 65, Issue 1, 2007, Pages 33-49

  Defaye, J ^a   Garcia Fernandez J M ^b   Ortiz Mellet, C ^c  

^a Laboratoire de Pharmacochimie   (France)

^b INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

^c UNIVERSITY OF SEVILLE   (Spain)

Author keywords

Cyclodextrins; Heterocluster effect; Lectins; Multivalency; Nanoparticles; Neoglycoconjugates: Glycodendrimers; Pharmaceutical applications; Protein carbohydrate interactions; Targeting

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; ALLIDEX GARLESSENCE; BENEXATE; BETA CYCLODEXTRIN; CEFDITOREN PIVOXIL; CEFOTIAM; CEPHALOSPORIN; CETRIZIN; CHLORAMPHENICOL; CHOLINESTERASE INHIBITOR; CISAPRIDE; CLOROCIL; COORDINAX; CYCLODEXTRIN; DEXAMETHASONE; DICLOFENAC; DIPHENHYDRAMINE; ESTRADIOL; FENTIAZAC; GARLIC EXTRACT; GLYCERYL TRINITRATE; GLYMESASON; ITRACONAZOLE; LIMAPROST; MELUSID FAST; MENAGARGLE; METHADONE; MITOEXTRA; MITOMYCIN; NICOGUM; NICOTINE; NICOTINE GUM; NIMESULIDE; NITROPEN; OMEBETA; OMEPRAZOLE; OPALMON; PENTAERYTHRITYL TETRANITRATE; PIROXICAM; PIROXICAM BETA CYCLODEXTRIN; PROSTAGLANDIN E1; PROSTAGLANDIN E2; PROSTAVASIN; STADA TRAVEL; SUGAMMADEX; TEGRA; TIAPROFENIC ACID; TRANSLLIUM; UNCLASSIFIED DRUG; UNINDEXED DRUG; VORICONAZOLE; ZIPRASIDONE;

ARTICLE; CELL HETEROGENEITY; CELL INTERACTION; CHEMICAL MODIFICATION; DRUG BIOAVAILABILITY; DRUG INDUSTRY; DRUG MONITORING; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; DRUG TARGETING; HEMOLYSIS; HUMAN; MACROMOLECULE; MOLECULAR INTERACTION; NEPHROTOXICITY; SOLUBILIZATION;

EID: 33846456676     PISSN: 00034509     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0003-4509(07)90015-2     Document Type: Article

References (44)

1. Villiers A. Sur la fermentation de la fécule par l'action du ferment butyrique. C R Acad Sci 1891 ; 112 : 536-8.
2. Cramer F. Einschlussverbindungen. Heidelberg: Springer; 1954, 115 pages.
3. Schmid G. Cyclodextrin glycosyltransferase production: yield enhancement by overexpression of cloned genes. Trends Biotechnol 1989; 7: 244-8.
4. French D. Chemistry and biochemistry of starch in Biochemistry series 1 vol 5 Biochemistry of carbohydrates. London: Butterworths; 1975, 269-335.
5. Lu D, Ballou C, Defaye J, Dell A. Synthesis of 6-deoxy- maltooligosaccharides and a study of their lipid-binding properties. Carbohydr Res 1987, 160: 171-84.
6. Franck DW, Gray JE, Weaver RN. Cyclodextrin nephrosis in the rat. Am J Pathol 1976; 83: 367-82.
7. Pitha J, Milecki J, Fales H, Pannell L, Uekama K. Hydroxypropyl-β- cyclodextrin: Preparation and characterization; effects on solubility of drugs. Int J Pharm 1986; 29: 73-82.
8. Zia V, Rajewski RA, Stella V. Effect of cyclodextrin charge on complexation of neutral and charged substrates: Comparison of (SBE) 7m-β-CD to HP-β-CDE. Pharm Res 2001; 18: 667-73.
9. Ohtani Y, Irie T, Uekama K, Fukunaga K, Pitha J. Differential effects of α-, β-, and γ-cyclodextrins on human erythrocytes. Eur J Biochem 1989; 186: 17-22.
10. Bost M, Laine V, Pilard F, Gadelle A, Defaye J, Perly B. The hemolytic properties of chemically modified cyclodextrins. J Incl Phenom Mol Rec Chem 1997; 29: 57-63.
11. Lainé V, Coste-Sarguet A, Gadelle A, Defaye J, Perly B, Djedaïni-Pilard F. Inclusion and solubilization properties of 6-S-glycosyl-6-thio derivatives of β-cyclodextrin. J Chem Soc Perkin Trans 2 1995; 1479-87.
12. Séance thématique de l'Académie nationale de Pharmacie du 21 octobre 1998. Ann Pharm Fr 1999 ; 57 : 213-46.
13. Lee YC, Lee RT. Carbohydrate-protein interactions: Basis of glycobiology. Acc Chem Res 1995; 28: 321-7.
14. Gestwicki JE, Cairo CW, Strong LE, Oetjen KA, Kiessling LL. Influencing receptor-ligand binding mechanisms with multivalent ligand architecture. J Am Chem Soc 2002; 124: 14922-33.
15. Lindhorst TK, Artificial multivalent sugar ligands to understand and manipulate carbohydrate-protein interactions. Top Curr Chem 2002; 218: 201-35.
16. Boturyn D, Coll J-L, Garanger E, Favrot M-C, Dumy P. Template assembled cyclopeptides as multimeric systems for integrin targeting and endocytosis. J Am Chem Soc 2004; 126: 5730-9.
17. Roy R, Kim JM. Amphiphilic p-tert-butylcalix [4]arene scaffolds containing exposed carbohydrate dendrons. Angew Chem Int Ed 1999; 38: 369-72.
18. Fulton DA, Stoddart JF, Neoglycoconjugates based on cyclodextrins and calixarenes. Bioconjugate Chem 2001; 12: 655-72.
19. Ortiz Mellet C, Defaye J, García Fernández JM. Multivalent cyclooligosaccharides: Versatile carbohydrate clusters with dual role as molecular receptors and lectin ligands. Chem Eur J 2002; 8: 1983-90.
20. André S, Kaltner H, Furuike T, Nishimura S-I, Gabius HJ. Persubstituted cyclodextrin-based glycoclusters as inhibitors of protein-carbohydrate recognition using purified plant and mammalian lectins and wild-type and lectine-gene-transfected tumor cells as targets. Bioconjugate Chem 2004; 15: 87-98.
21. García Fernandez JM, Ortiz Mellet C, Defaye J. Glyconanocavities: Cyclodextrins and beyond. J Incl Phenom Macrocycl Chem 2006; 56: 149-59.
22. Gadelle A, Defaye J. Selective halogenation at primary positions of cyclomaltooligosaccharides and a synthesis of per(3,6)-anhydro cyclomaltooligosaccharides. Angew Chem Int Ed 1991; 30: 78-9.
23. Gorin BI, Riopelle RJ, Thatcher GRJ. Efficient perfacial derivatization of cyclodextrins at the primary face. Tetrahedron Lett 1996; 37: 4647-50.
24. Chmurski K, Defaye J. Regioselective halogenation of primary alcohol groups of cyclodextrins with halomethylenemorpholinium halides Vilsmeier-Haack reagents. Polish J Chem 1999; 73: 967-71.
25. Chmurski K, Defaye J. An improved synthesis of per(6-deoxyhalo) cyclodextrins using N-halosuccinimides-triphenyphosphine in dimethylformamide. Supramol Chem 2000; 12: 221-4.
26. nd 2004 Glasgow; abstract P14.
27. Defaye J, Crouzy S, Evrard N, Law H. Regioselective method for preparation of C-6 monosulfonylated cyclodextrins. WO 99 61,483; Chem Abstr 2000; 132: 24077a.
28. Baussanne I, Benito JM, Ortiz Mellet C, García Fernández JM, Law H, Defaye J. Synthesis and comparative lectin-binding affinity of mannosyl-coated β-cyclodextrindendrimer constructs. Chem Commun 2000; 1489-90.
29. Khan AR, Forgo P, Stine KJ, D'Souza VT. Methods for selective modifications of cyclodextrins. Chem Rev 1998; 98: 1977-96.
30. García Fernández J M, Ortiz Mellet C. Chemistry and developments of N-thiocarbonyl carbohydrate derivatives: sugar isothiocyanates, thioamides, thioureas, thiocarbamates, and their conjugates. Adv Carbohydr Chem Biochem 1999; 55: 36-135.
31. Defaye J, Ortiz Mellet C, García Fernández JM. Thioureidocyclodextrins particularly useful for solubilizing antitumoral and antiparasitic agents and methods for preparing same. WO 97 33,919; Chem Abstr 1997; 127: 264489.
32. Riou L, Ghezzi C, Wouessidjewe D, Law H, Mathieu J-P, Defaye J, et al. Differential effects of cyclodextrins and derivatives on the biological behaviour of the myocardial perfusion imaging agent 99mTcN-NOET. Eur J Pharm Biopharm 2005; 61: 40-9.
33. Boas U, Heegard PMH. Dendrimers in drug research. Chem Soc Rev 2004; 33: 43-63.
34. Benito JM, Gómez-García M, Ortiz Mellet C, Baussanne I, Defaye J, Garcia Fernández JM. Optimizing saccharide-directed molecular delivery to biological receptors: Design, synthesis, and biological evaluation of glycodendrimer-cyclodextrin conjugates. J Am Chem Soc 2004; 126: 10355-63.
35. Baussanne I, Benito JM, Ortiz Mellet C, García Fernández JM, Defaye J. ChemBioChem 2001; 2: 777-83.
36. Defaye J, Ortiz Mellet C, García Fernández JM, Benito JM, Gómez García M, Yu J-X. New cyclodextrin dimers and their derivatives, their preparation processes and their use in particular for solubilization of active substances. WO 05 4303; Chem Abstr 2005; 142: 482242.
37. Bom A, Bradley M, Cameron K, Clark KJ, van Egmond J, Feilden H, et al. A novel concept of reversing neuromuscular block: chemical encapsulation of rocuronium bromide by a cyclodextrin-based synthetic host. Angew Chem Int Ed 2002; 41: 266-70.
38. Ortiz Mellet C, Benito JM, García Fernández JM, Law H, Chmurski K, Defaye J. Cyclodextrin-scaffolded glycoclusters. Chem Eur J 1998; 4: 2523-31.
39. Gómez-García M, Benito JM, Rodríguez-Lucena D, Yu J-X, Chmurski K, Ortiz Mellet C, et al. Probing secondary carbohydrate-protein interactions with highly dense cyclodextrin-centered heteroglycoclusters: The heterocluster effect. J Am Chem Soc 2005; 127: 7970-1.
40. Wileman TE, Lennartz MR, Stahl PD. Identification of the macrophage mannose receptor as a 175-kDa membrane protein. Proc Natl Acad Sci USA 1986; 83: 2501-5.
41. Lee J. Nanoparticle formulation increases oral bioavailability of poorly soluble drugs: Approaches, experimental evidence and theory. Curr Nanosci 2005; 1: 237-43.
42. Willis RC, Good things in small packages: Nanotech advances are producing mega-results in drug delivery. Modern Drug Discovery 2004; 7: 30-6.
43. Skiba M, Wouessidjewe D, Puisieux F, Duchêne D, Gulik A. Characterization of amphiphilic β-cyclodextrin nanospheres. Int J Pharm 1996; 142: 121-4.
44. Defaye J, Gèze A, Wouessidjewe D, Balbuena P, Gómez García M, Ortiz Mellet C, et al. Surface-modulable nanoparticles and cell transfection systems based on cyclodextrins. Int. Carbohydr. Symp. 23rd Vancouver-Whistler; July 2006; abstract C-3 p. 228.