Bilayer vesicles of amphiphilic cyclodextrins: Host membranes that recognize guest molecules

Chemistry - A European Journal

Volumn 11, Issue 4, 2005, Pages 1171-1180

  Falvey, Patrick ^a   Lim, Choon Woo ^b   Darcy, Raphael ^a   Revermann, Tobias ^b   Karst, Uwe ^b   Giesbers, Marcel ^c   Marcelis, Antonius T M ^c   Lazar, Adina ^d   Coleman, Anthony W ^d   Reinhoudt, David N ^b   Ravoo, Bart Jan ^b  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b UNIVERSITY OF TWENTE   (Netherlands)

^c WAGENINGEN UNIVERSITY   (Netherlands)

^d INSTITUT DE BIOLOGIE ET CHIMIE DES PROTÉINES   (France)

Author keywords

Amphiphiles; Cyclodextrins; Membranes; Molecular recognition; Vesicles

Indexed keywords

ALKYLATION; ISOTHERMS; LIGHT SCATTERING; MOLECULES; POLYETHYLENE GLYCOLS; SOLUTIONS; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION;

BILAYERS; CYCLODEXTRINES; DYE ENCAPSULATION; VESCILES;

MEMBRANES;

ADAMANTANE CARBOXYLATE; ADAMANTANE DERIVATIVE; ALKYL GROUP; ALPHA CYCLODEXTRIN; AMPHOPHILE; ANION; BETA CYCLODEXTRIN; CARBOXYLIC ACID DERIVATIVE; CYCLODEXTRIN; DYE; GAMMA CYCLODEXTRIN; GLASS; MACROGOL; UNCLASSIFIED DRUG; WATER;

ALKYLATION; AQUEOUS SOLUTION; ARTICLE; BILAYER MEMBRANE; BINDING AFFINITY; CAPILLARY ELECTROPHORESIS; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; ELECTROPHORETIC MOBILITY; ENCAPSULATION; HYDROPHOBICITY; LIGHT SCATTERING; MOLECULAR RECOGNITION; MOLECULAR SIZE; STRUCTURE ANALYSIS; SURFACE PROPERTY; SYNTHESIS; THICKNESS; TRANSMISSION ELECTRON MICROSCOPY; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

AIR; CYCLODEXTRINS; GLASS; LIPID BILAYERS; MEMBRANES, ARTIFICIAL; SURFACE PROPERTIES; SURFACE-ACTIVE AGENTS; WATER; X-RAY DIFFRACTION;

EID: 20044373998     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400905     Document Type: Article

References (59)

1. R. C. Fetter, J. S. Salek, C. T. Sikorski, G. Kumaravel, F. T. Lin, J. Am. Chem. Soc. 1990, 112, 3860-3868.
2. a) H. Parrot-Lopez, C.-C. Ling, P. Zhang, A. Baszkin, G. Albrecht, C. de Rango, A. W. Coleman, J. Am. Chem. Soc. 1992, 114, 5479-5480;
3. b) A. Schalchli, J. J. Benattar, P. Tschoreloff, P. Zhang, A. W. Coleman, Langmuir 1993, 9, 1968-1970;
4. c) P. C. Tschoreloff, M. M. Boissonnade, A. W. Coleman, A. Baszkin, Langmuir 1995, 11, 191-196.
5. a) M. Skiba, D. Duchêne, F. Puisieux, D. Wouessidjewe, Int. J. Pharm. 1996, 129, 113-121;
6. b) A. Gulik, H. Delacroix, D. Wouessidjewe, M. Skiba, Langmuir 1998, 14, 1050-1057.
7. a) R. Auzély-Velty, F. Djedaïni-Pilard, S. Désert, B. Perly, T. Zemb, Langmuir 2000, 16, 3727-3734;
8. b) R. Auzély-Velty, C. Péan, F. Djedaïni-Pilard, T. Zemb, B. Perly, Langmuir 2001, 17, 504-510.
9. a) A. Mazzaglia, B. J. Ravoo, R. Darcy, P. Gambadauro, F. Mallamace, Langmuir 2002, 18, 1945-1948;
10. b) D. Lombarde, A. Longo, R. Darcy, A. Mazzaglia, Langmuir 2004, 20, 1057-1062.
11. a) B. J. Ravoo, R. Darcy, Angew. Chem. 2000, 112, 4494-4496; Angew. Chem. Int. Ed. 2000, 39, 4324-4326;
12. a) B. J. Ravoo, R. Darcy, Angew. Chem. 2000, 112, 4494-4496; Angew. Chem. Int. Ed. 2000, 39, 4324-4326;
13. b) D. Nolan, R. Darcy, B. J. Ravoo, Langmuir, 2003, 19, 4469-4472;
14. c) B. J. Ravoo, J. C. Jacquier, G. Wenz, Angew. Chem. 2003, 115, 2112-2116; Angew. Chem. Int. Ed. 2003, 42, 2066-2070;
15. c) B. J. Ravoo, J. C. Jacquier, G. Wenz, Angew. Chem. 2003, 115, 2112-2116; Angew. Chem. Int. Ed. 2003, 42, 2066-2070;
16. d) A. Mazzaglia, D. Forde, D. Garozzo, P. Malvagna, B. J. Ravoo, R. Darcy, Org. Biomol. Chem. 2004, 2, 957-960.
17. T. Sukegawa, T. Furuike, K. Niikura, A. Yamagishi, K. Monde, S.-I. Nishimura, Chem. Commun. 2002, 430-431.
18. R. Donohue, A. Mazzaglia, B. J. Ravoo, R. Darcy, Chem. Commun. 2002, 2864-2865.
19. a) M. J. Pregel, L. Jullien, J.-M. Lehn, Angew. Chem. 1992, 104, 1695-1699; Angew. Chem. Int. Ed. Engl. 1992, 57, 1637-1640;
20. a) M. J. Pregel, L. Jullien, J.-M. Lehn, Angew. Chem. 1992, 104, 1695-1699; Angew. Chem. Int. Ed. Engl. 1992, 57, 1637-1640;
21. b) L. Jullien, T. Lazrak, J. Canceill, L. Lacombe, J.-M. Lehn, J. Chem. Soc. Perkin Trans. 2 1993, 1011-1020;
22. c) J. Lin, C. Creminon, B. Perly, F. Djedaïni-Pilard, J. Chem. Soc. Perkin Trans. 2 1998, 2639-2646;
23. d) R. Auzély-Velty, B. Perly, O. Taché, T. Zemb, P. Jéhan, P. Guenot, J. P. Dalbiez, F. Djedaïni-Pilard, Carbohydr. Res. 1999, 318, 82-90.
24. a) D. Y. Sasaki, T. A. Waggoner, J. A. Last, T. M. Alam, Langmuir 2002, 18, 3714-3721;
25. b) E. L. Doyle, C. A. Hunter, H. C. Phillips, S. J. Webb, N. H. Williams, J. Am. Chem. Soc. 2003, 125, 4593-4599;
26. c) B. Bondurant, J. A. Last, T. A. Waggoner, A. Slade, D. Y. Sasaki, Langmuir 2003, 19, 1829-1837;
27. d) J. Huskens, A. Mulder, T. Auletta, C. A. Nijhuis, M. J. W. Ludden, D. N. Reinhoudt, J. Am. Chem. Soc. 2004, 126, 6784-6797;
28. e) V. Marchi-Artzner, M.-J. Brienne, T. Gulik-Krzywicki, J. C. Dedieu, J.-M. Lehn, Chem. Eur. J. 2004, 10, 2342-2350.
29. a) M. Mammen, S.-K. Choi, G. M. Whitesides, Angew. Chem. 1998, 110, 2908-2953; Angew. Chem. Int. Ed. 1998, 37, 2754-2794;
30. a) M. Mammen, S.-K. Choi, G. M. Whitesides, Angew. Chem. 1998, 110, 2908-2953; Angew. Chem. Int. Ed. 1998, 37, 2754-2794;
31. b) L. L. Kiessling, J. E. Gestwicki, L. E. Strong, Curr. Opin. Chem. Biol. 2000, 4, 696-703.
32. F. Guillo, B. Hamelin, L. Jullien, J. Canceill, J.-M. Lehn, L. de Robertis, H. Driguez, Bull. Soc. Chim. Fr. 1995, 132, 857-866.
33. A. Gadelle, J. Defaye, Angew. Chem. 1991, 103, 94-95; Angew. Chem. Int. Ed. Engl. 1991, 30, 78-79.
34. A. Gadelle, J. Defaye, Angew. Chem. 1991, 103, 94-95; Angew. Chem. Int. Ed. Engl. 1991, 30, 78-79.
35. Y. Kawabata, M. Matsumoto, M. Tanaka, H. Takahashi, Y. Irinatsu, S. Tamura, Y. Tagaki, H. Nakahara, K. Fukuda, Chem. Lett. 1986, 1933-1934.
36. C.-C. Ling, R. Darcy, W. Risse, J. Chem. Soc. Chem. Commun. 1993, 438-440.
37. K. Kobayashi, K. Kajikawa, H. Sasabe, W. Knoll, Thin Solid Films 1999, 549, 244-249.
38. A. Mazzaglia, R. Donohue, B. J. Ravoo, R. Darcy, Eur. J. Org. Chem. 2001, 1715-1721.
39. D. A. van Hal, J. A. Bouwstra, A. van Rensen, E. Jeremiasse, T. de Vringer, H. E. Junginger, J. Colloid Interface Sci. 1996, 178, 263-273.
40. F. Szoka, D. Papahadjopoulos, Proc. Natl. Acad. Sci. USA 1978, 75, 4194-4198.
41. L. Jullien, J. Canceill, L. Lacombe, J.-M. Lehn, J. Chem. Soc. Perkin Trans. 2 1994, 989-1002.
42. The X-ray diffraction spectra for 7a and 7b show no higher order reflections. Instead, a broad peak is found at 14.5 Å. This could be the distance between the cyclodextrin rings.
43. 2, approximately 50000 molecules of cyclodextrin would be required to make a 160 nm diameter unilamellar vesicle.
44. 2 vibrations was evident only in the parallel (Brewster angle) configuration, not in the perpendicular (transmission) configuration, a fact indicating that the chains are mostly oriented perpendicular to the bilayer surface.
45. J. M. Seddon, G. Cevc in Phospholipids Handbook (Ed.: G. Cevc), Marcel-Dekker, New York, 1993, pp 403-454.
46. P. Shahgaldian, M. Cesario, P. Goreloff, A.W. Coleman, Chem. Commun. 2002, 326-327.
47. a) W. C. Cromwell, K. Byström, M. R. Eftink, J. Phys. Chem. 1985, 89, 326-332;
48. b) M. Weickenmeier, G. Wenz, Macromol. Rapid Commun. 1996, 17, 731-736.
49. I. J. Colton, J. D. Carbeck, J. Rao, G. M. Whitesides, Electrophoresis 1998, 19, 367-382.
50. B. J. Ravoo, J.-C. Jacquier, Macromolecules 2002, 35, 6412-6416.
51. a) M. A. Roberts, L. Locascio-Brown, W. A. MacCrehan, R. A. Durst, Anal. Chem. 1996, 68, 3434-3440;
52. b) K. Kawakami, Y. Nishihara, K. Hirano, Langmuir 1999, 15, 1893-1895;
53. c) S. K. Wiedmer, J. Hautala, J. M. Holopainen, P. K. J. Kinnunen, M. L. Riekkola, Electrophoresis 2001, 22, 1305-1313;
54. d) C. F. Duffy, S. Gafoor, D. P. Richards, H. Admadzadeh, R. O'Kennedy, E. A. Arriaga, Anal. Chem. 2001, 73, 1855-1861;
55. e) A. N. Phayre, H. M. V. Farfano, M. A. Hayes, Langmuir 2002, 18, 6499-6503;
56. f) J. McKeon, M. G. Khaledi, J. Chromatogr. A 2003, 1004, 39-46.
57. a) Y. H. M. Chan, R. Schweiss, C. Werner, M. Grunze, Langmuir 2003, 19, 7380-7385:
58. b) M. Johnsson, A. Wagenaar, J. B. F. N. Engberts, J. Am. Chem. Soc. 2003, 125, 757-760.
59. I. N. Topchieva, P. Mischnick, G. Kühn, V. A. Polyakov, S. V. Elezkaya, G. I. Bystryzky, K. I. Karezin, Bioconjugate Chem. 1998, 9, 676-682.