Amphiphilic cyclodextrins - Advances in synthesis and supramolecular chemistry

European Journal of Organic Chemistry

Volumn , Issue 6, 2008, Pages 957-969

  Sallas, Florence ^a   Darcy, Raphael ^a  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Amphiphilic cyclodextrin; Drug delivery; Gene delivery; Self assembly; Supramolecular chemistry

Indexed keywords

EID: 53649086639     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700933     Document Type: Short Survey

References (104)

1. J. Szejtli, T. Osa, Comprehensive Supramolecular Chemistry, vol. 3, Pergamon, Oxford, 1996, (Cyclodextrins).
2. For a review, see: J. Szejtli, Chem. Rev. 1998, 98, 1743-1753.
3. S. Shinkai, S. Mori, H. Koreishi, T. Tsubaki, O. Manabe, J. Am. Chem. Soc. 1986, 108, 2409-2416.
4. a) B. Harten, R. Darcy, R. Lyons, Nouv. J. Chim. 1986, 10, 569-571;
5. b) R. Darcy, B. Harten, Proc. Royal Irish Acad. 1989, 89B, 135-141;
6. c) Y. Hui, W. Zou, in Frontiers in Supramolecular Organic Chemistry and Photochemistry (Eds.: H.-J. Schneider, H. Dürr), VCH, Weinheim, 1991, 203;
7. d) H. Nakatani, K. I. Shibata, H. Kondo, K. Hiromi, Biopolymers 1997, 16, 2363-2370.
8. R. Breslow, S. D. Dong, Chem. Rev. 1998, 98, 1997-2011.
9. a) K. H. Frömming, J. Szejtli, Cyclodextrins in Pharmacy, Kluwer, Dordrecht, 1994;
10. b) K. Uekama, F. Hirayama, T. Irie, Chem. Rev. 1998, 98, 2045-2076.
11. M. V. Rekharsky, Y. Inoue, Chem. Rev. 1998, 98, 1875-1917.
12. N. Nakashima, T. Kawabuchi, H. Murakami, J. Incl. Phenom. Macro. Chem. 1998, 32, 363-373.
13. Y. Kawabata, M. Matsumoto, M. Tanaka, H. Takahashi, Y. Irinatsu, S. Tamara, W. Tagaki, H. Nakahara, K. Fukuda, Chem. Lett. 1986, 11, 1933-1934.
14. C.-C. Ling, R. Darcy, W. Risse, J. Chem. Soc. Chem. Commun. 1993, 438-440.
15. a) For a review, see: A. Mazzaglia, B. J. Ravoo, R. Darcy, P. Gambadauro, F. Mallamace, Langmuir 2002, 18, 1945-1948 and refs therein;
16. b) P. Zhang, C. C. Ling, A. W. Coleman, H. Parrot-Lopez, H. Galons, Tetrahedron Lett. 1991, 32, 2769-2770;
17. c) 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.
18. a) B. Brady, N. Lynam, T. O'Sullivan, C. Ahern, R. Darcy in Organic Syntheses, vol. 77 (Ed.: D. J. Hart), Wiley, New York, 2000, pp. 220-224;
19. b) H.-S. Byun, N. Zhong, R. Bittman, ibid., pp. 225-230.
20. A. Gadelle, J. Defaye, Angew. Chem. Int. Ed. Engl. 1991, 30, 78-80.
21. A. R. Khan, P. Forgo, K. J. Stine, V. T. D'Souza, Chem. Rev. 1998, 98, 1977-1996.
22. M. Wazynska, A. Temeriusz, K. Chmurski, R. Bilewicz, J. Jurczak, Tetrahedron Lett. 2000, 41, 9119-9123.
23. N. Badi, N. Jarroux, P. Guégan, Tetrahedron Lett. 2006, 47, 8925-8927.
24. E. Memisoglu, A. Bochot, M. Sen, D. Charon, D. Duchene, A. A. Hincal, J. Pharm. Sci. 2002, 91, 1214-1224.
25. B. Hamelin, L. Jullien, A. Laschewsky, Chem. Eur. J. 1999, 5, 546-556.
26. a) K. Chmurski, A. W. Coleman, J. Jurczak, J. Carbohydr. Chem. 1996, 15, 787-796;
27. b) K. Chmurski, R. Bilewicz, J. Jurczak, Langmuir 1996, 12, 6114-6118.
28. K. Imamura, H. Ikeda, A. Ueno, Chem. Lett. 2002, 516-517.
29. C.-C. Ling, R. Darcy, J. Chem. Soc. Chem. Commun. 1993, 203-205.
30. 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.
31. a) F. Djedaïni-Pilard, R. Auzely-Velty, B. Perly, Recent Res. Devel. Org. Bioorg. Chem. 2002, 5, 41-57.
32. Transworld Research Network, Kerala, India; b) S. Moutard, B. Perly, P. Gode, G. Demailly, F. Djedaïni-Pilard, J. Incl. Phenom. Macro. Chem. 2002, 44, 317-322;
33. c) M. Roux, S. Moutard, B. Perly, F. Djedaïni-Pilard, Biophys. J. 2007, 93, 1620-1629.
34. a) R. Auzély-Velty, F. Djedaïni-Pilard, S. Désert, B. Perly, T. Zemb, Langmuir 2000, 16, 3727-3734;
35. b) R. Auzély-Velty, C. Péan, F. Djedaïni-Pilard, T. Zemb, B. Perly, Langmuir 2001, 17, 504-510.
36. a) B. J. Ravoo, R. Darcy, Angew. Chem. Int. Ed. 2000, 39, 4324-4326;
37. b) A. Mazzaglia, R. Donohue, B. J. Ravoo, R. Darcy, Eur. J. Org. Chem. 2001, 1715-1721;
38. c) P. Falvey, C. W. Lim, R. Darcy, T. Revermann, U. Karst, M. Giesbers, A. T. M. Marcelis, A. Lazar, A. W. Coleman, D. N. Reinhoudt, B. J. Ravoo, Chem. Eur. J. 2005, 11, 1171-1180.
39. R. Donohue, A. Mazzaglia, B. J. Ravoo, R. Darcy, Chem. Commun. 2002, 2864-2865.
40. S. A. Cryan, R. Donohue, B. J. Ravoo, R. Darcy, C. M. O'Driscoll, J. Drug Deliv. Sci. Technol. 2004, 14, 57-62.
41. R. Donohue, Ph. D. Thesis, University College Dublin 2002, Dublin, Ireland.
42. A. Leydet, C. Moullet, J. P. Roque, M. Witvrouw, C. Pannecouque, G. Andrei, R. Snoeck, J. Neyts, D. Schols, E. De Clercq, J. Med. Chem. 1998; 41, 4927-4932.
43. T. Kraus, M. Budesinsky, J. Zavada, J. Org. Chem. 2001, 66, 4595-4600.
44. H. H. Baer, Y. Shen, F. Santoyo Gonzalez, A. Vargas Berenguel, J. Isac Garcia, Carbohydr. Res. 1992, 235, 129-139.
45. a) A. Dubes, D. Bouchu, R. Lamartine, H. Parrot-Lopez, Tetrahedron Lett. 2001, 42, 9147-9151;
46. b) A. Dubes, G. Degobert, H. Fessi, H. Parrot-Lopez, Carbohydr. Res. 2003, 338, 2185-2193.
47. S. Lesieur, D. Charon, P. Lesieur, C. Ringard-Lefébvre, V. Muguet, D. Duchêne, D. Wouessidjewe, Chem. Phys. Lipids 2000, 106, 127-144.
48. T. Sukegawa, T. Furuike, K. Niikura, A. Yamagishi, K. Monde, S.-I. Nishimura, Chem. Commun. 2002, 430-431.
49. P. Schwinté, M. Ramphul, R. Darcy, J. F. O'Sullivan, J. Incl. Phenom. Macro. Chem. 2003, 47, 109-112.
50. M. Ramphul, Ph. D. Thesis, University College Dublin 1998, Dublin, Ireland.
51. a) E. Kissa, Fluorinated Surfactants, Properties, Applications; Surfactant Science Series, Marcel Dekker, New York, 1994, vol. 50;
52. b) V. Ravilly, S. Gaentzler, C. Santaella, P. Vierling, Helv. Chim. Acta 1996, 79, 405-425;
53. c) F. Guillod, J. Geiner, J. G. Riess, Chem. Phys. Lipids 1995, 78, 149-182.
54. C. E. Granger, C. P. Félix, H. P. Parrot-Lopez, B. R. Langlois, Tetrahedron Lett. 2000, 41, 9257-9260.
55. a) S. Péroche, H. Parrot-Lopez, Tetrahedron Lett. 2003, 44, 241-245;
56. b) S. Péroche, G. Degobert, J.-L. Putaux, M.-G. Blanchin, H. Fessi, H. Parrot-Lopez, Eur. J. Pharm. Biopharm. 2005, 60, 123-131.
57. D. Nolan, Ph. D. Thesis, University College Dublin, 2005, Dublin, Ireland.
58. K. T. Lim, H. S. Ganapathy, M. Y. Lee, H. Yuvaraj, W.-K. Lee, H. Heo, J. Fluorine Chem. 2006, 127, 730-735.
59. F. Sallas, K. Niikura, S.-I. Nishimura, Chem. Commun. 2004, 596-597.
60. A. Mazzaglia, D. Forde, D. Garozzo, P. Malvagna, B. J. Ravoo, R. Darcy, Org. Biomol. Chem. 2004, 2, 957-960.
61. a) S. McNicholas, A. Rencurosi, L. Lay, A. Mazzaglia, L. Sturiale, M. Perez, R. Darcy, Biomacromolecules 2007, 8, 1851-1857;
62. 2O mixture was used instead. Also, full deacetylation of the C16 CD was not possible due to solubility problems.
63. D. A. Fulton, J. F. Stoddart, J. Org. Chem. 2001, 66, 8309-8319.
64. S. Mc Nicholas, Ph. D. Thesis, University College Dublin, 2005, Dublin, Ireland.
65. A. Salameh, A. N. Lazar, A. W. Coleman, H. Parrot-Lopez, Tetrahedron 2005, 61, 8740-8745.
66. a) P. C. Tschoreloff, M. M. Boissonnade, A. W. Coleman, A. Baszkin, Langmuir 1995, 11, 191-196;
67. A. Schalchli, J. J. Benattar, P. Tchoreloff, P. Zhang, A. W. Coleman, Langmuir 1993, 9, 1968-1970;
68. b) A. Kasselouri, A. W. Coleman, A. Baszkin, J. Colloid Interface Sci. 1996, 180, 384-397;
69. c) A. Kasselouri, A. W. Coleman, G. Albrecht, A. Baszkin, J. Colloid Interface Sci. 1996, 180, 398-404;
70. d) M. Skiba, C. Morvan, D. Duchêne, F. Puisieux, D. Wouessidjewe, Int. J. Pharm. 1995, 126, 275-279;
71. e) M. Skiba, D. Duchêne, F. Puisieux, D. Wouessidjewe, Int. J. Pharm. 1996, 129, 113-121;
72. f) A. Gulik, H. Delacroix, D. Wouessidjewe, M. Skiba, Langmuir 1998, 14, 1050-1057;
73. g) C. Ringard-Lefévre, A. Bochot, E. Minesoǧlu, D. Charon, D. Duchêne, A. Baszkin, Colloids Surf. B 2002, 25, 109-117.
74. P. Schwinté, R. Darcy, J. Dey, C.-C. Ling, J. Chem. Soc. Perkin Trans. 2 1998, 1513-1516.
75. a) J. N. Israelachvilli, Intermolecular and Surface Forces: With Application to Colloidal and Biological Systems, Academic Press, New York, 1985;
76. b) J.-H. Fuhrhop, J. Koning, Membranes and Molecular Assemblies: The Synkinetic Approach, Royal Society of Chemistry, Cambridge, 1994.
77. a) R Darcy, B. J. Ravoo, A. Mazzaglia, E. Kan, C. M. O'Driscoll, Proceedings Twelfth International Symposium on Cyclodextrins, Kluwer Academic, Dordrecht, 2004, 665;
78. b) R. Darcy, L. J. Penkler, B. J. Ravoo, PCT/IE01/00057, 2002.
79. R. C. Petter, J. S. Salek, C. T. Sikorski, G. Kumaravel, F.-T. Lin, J. Am. Chem. Soc. 1990, 112, 3860-3868.
80. D. Lombardo, A. Longo, R. Darcy, A. Mazzaglia, Langmuir 2004, 20, 1057-1064.
81. D. Nolan, R. Darcy, B. J. Ravoo, Langmuir 2003, 19, 4469-4472.
82. a) A. Mazzaglia, N. Micali, L. Monsù Scolaro, see chapter Structural Characterization of Colloidal Cyclodextrins: Molecular Recognition by means of Photophysical Investigation in Cyclodextrins Materials: Photochemistry, Photophysics and Photobiology (Ed.: A. Douhal), Elsevier, 2006, pp. 203-222;
83. b) A. Mazzaglia, L. Monsù Scolaro, R. Darcy, R. Donohue, B. J. Ravoo, J. Incl. Phenom. Mol. Recogn. Chem. 2002, 44, 127-132.
84. a) A. Mazzaglia, N. Angelini, D. Lombardo, N. Micali, S. Patane, V. Villari, L. Monsú Scolaro, J. Phys. Chem. B 2005, 109, 7258-7265;
85. b) A. Mazzaglia, N. Angelini, R. Darcy, R. Donohue, D. Lombardo, N. Micali, M. T. Sciortino, V. Villari, L. Monsú Scolaro, Chem. Eur. J. 2003, 9, 5762-5769.
86. S. Sortino, A. Mazzaglia, L. Monsù Scolaro, F. Marino Merlo, V. Valveri, M. T. Sciortino, Biomaterials 2006, 27, 4256-4265.
87. S. Sortino, S. Petralia, R. Darcy, R. Donohue, A. Mazzaglia, New J. Chem. 2003, 27, 602-608.
88. L. Valli, G. Giancane, A. Mazzaglia, L. Monsù Scolaro, S. Conoci, S. Sortino, J. Mater. Chem. 2007, 17, 1660-1663.
89. a) B. J. Ravoo, R. Darcy, A. Mazzaglia, D. Nolan, K. Gaffney, Chem. Commun. 2001, 827-828;
90. b) T. Kraus, M. Buděšínský, I. Císařová, J. Závada, Angew. Chem. Int. Ed. 2002, 41, 1715-1717.
91. a) N. Benkirane-Jessel, P. Schwinté, P. Falvey, R. Darcy, Y. Haïkel, P. Schaaf, J.-C. Voegel, J. Ogier, Adv. Funct. Mater. 2004, 14, 174-182;
92. b) N. Benkirane-Jessel, P. Schwinté, R. Donohue, P. Lavalle, F. Boulmedais, R. Darcy, B. Szalontai, J.-C. Voegel, J. Ogier, Adv. Funct. Mater. 2004, 14, 963-969.
93. B. J. Ravoo, J.-C. Jacquier, G. Wenz, Angew. Chem. Int. Ed. 2003, 42, 2066-2070.
94. a) C. W. Lim, B. J. Ravoo, D. N. Reinhoudt, Chem. Commun. 2005, 5627-5629;
95. b) C. W. Lim, O. Crespo-Biel, M. C. A. Stuart, D. N. Reinhoudt, J. Huskens, B. J. Ravoo, Proc. Natl. Acad. Sci. USA 2007, 104, 6986-6991.
96. a) N. Micali, V. Villari, A. Mazzaglia, L. Monsú Scolaro, A. Valerio, A. Rencurosi, L. Lay, Nanotechnology 2006, 17, 3239-3244;
97. b) A. Mazzaglia, A. Valerio, V. Villari, A. Rencurosi, L. Lay, S. Spadaro, L. Monsù Scolaro, N. Micali, New J. Chem. 2006, 30, 1662-1668.
98. C. O'Driscoll, R. Darcy, Business Briefing: Pharmatech. 2002, 1-5 (www.bbriefings.com/pdf/17/ACF9C6C.pdf).
99. a) D. Luo, M. W. Saltzman, Nat. Biotechnol. 2000, 18, 33-37;
100. b) W. Li, F. C. Szoka Jr, Pharm. Res. 2007, 24, 438-449.
101. S. A. Cryan, A. Holohan, R. Donohue, R. Darcy, C. M. O'Driscoll, Eur. J. Pharm. Sci. 2004, 21, 625-633.
102. a) D. D. Lasic, H. Strey, M. C. A. Stuart, R. Podgornik, P. Frederik, J. Am. Chem. Soc. 1997, 119, 832-833;
103. b) N. S. Templeton, D. D. Lasic, P. M. Frederik, H. H. Strey, D. D. Roberts, G. N. Pavlakis, Nat. Biotechnol. 1997, 15, 647-652.
104. Macrocyclocyclic molecule: a macrocyclic molecule composed of cyclic units.