Synthesis and interfacial properties of amphiphilic β-cyclodextrins and their substitution at the O-6 position with a mono bio-recognisable galactosyl antenna

Tetrahedron

Volumn 61, Issue 36, 2005, Pages 8740-8745

  Salameh, Alain ^a   Lazar, Adina N ^b   Coleman, Anthony W ^b   Parrot Lopez, Hélène ^a  

^a UNIVERSITÉ LYON 1   (France)

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

Author keywords

Amphiphilic cyclodextrin; Galactosyl antenna; Langmuir isotherms

Indexed keywords

6 AMINO 6 DEOXYHEPTAKIS(2,3 BIS O HEXANOYL)CYCLOMALTOHEPTAOSE; 6 AZIDO 6 DEOXYHEPTAKIS(2,3 BIS O HEXANOYL)CYCLOMALTOHEPTAOSE; 6 AZIDO 6 DEOXYHEXAKIS(6 O TERT BUTYLDIMETHYLSILYL)CYCLOMALTOHEPTAOSE; 6 AZIDO 6 DEOXYHEXAKIS(6 O TERT BUTYLDIMETHYLSILYL)HEPTAKIS(2,3 BIS O HEXANOYL)CYCLOMALTOHEPTAOSE; 6 DEOXY 6 [9 (BETA DEXTRO GALACTOPYRANOSYLAMINO) 1,9 DIOXONONANOYL] AMINOHEPTAKIS(2,3 BIS O HEXANOYL)CYCLOMALTOHEPTAOSE; AMPHOPHILE; BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; GALACTOSE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; CROSS COUPLING REACTION; DRUG SYNTHESIS; ELECTROSPRAY MASS SPECTROMETRY; ISOTHERM; MOLECULE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 23444433378     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.06.054     Document Type: Article

References (26)

1. K. Uekama, F. Hirayama, and T. Irie Chem. Rev. 98 1998 2045 2076
2. D. Duchêne News Trends in Cyclodextrin and Derivatives 1991 Edition de Santé Paris
3. J. Szejtli Med. Res. Rev. 14 1994 353 386
4. J. Szejtli Cyclodextrin Technology 1998 Kluwer Academic Dordrecht
5. F. Attioui, A. Al-Omar, E. Leray, H. Parrot-Lopez, C. Finance, and R. Bonaly Biol. Cell. 82 1994 161 167
6. C. Ortiz-Mellet, J. Defaye, and J.M. Garcia-Fernandez Chem. Eur. J. 8 2002 1982 1990
7. T. Furuike, S. Aiba, and S.I. Nishimura Tetrahedron 56 2000 9909 9915
8. F. Sallas, K. Niikura, and S.I. Nishimura Chem. Commun. 2004 596 597
9. M. Tanaka, R. Azumi, H. Tachibana, T. Nakamura, Y. Kawabata, M. Matsumoto, T. Miyasaka, W. Tagaki, H. Nakahara, and K. Fukuda Thin Solid Films 244 1994 832 835
10. M. Greenhall, P. Lukes, R. Kataky, N.E. Agbor, J.P. Badyal, J. Yarwood, D. Parker, and M.C. Petty Langmuir 11 1995 3997 4000
11. P. Zhang, C.C. Ling, A.W. Coleman, H. Parrot-Lopez, and H. Galons Tetrahedron Lett. 32 1991 2769 2770
12. A. Mazzaglia, R. Donohue, B.J. Ravoo, and R. Darcy Eur. J. Org. Chem. 2001 1715 1721
13. C. Granger, C. Félix, H. Parrot-Lopez, and B. Langlois Tetrahedron Lett. 41 2000 9257 9260
14. T. Sukegawa, T. Furuike, K. Niikura, A. Yamagishi, K. Monde, and S.I. Nishimura Chem. Commun. 2002 430 431
15. S. Peroche, and H. Parrot-Lopez Tetrahedron Lett. 44 2003 241 245
16. R. Auzély-Velty, B. Perly, O. Taché, T. Zemb, P. Jéhan, P. Guenot, J.P. Dalbiez, and F. Djedaïni-Pilard Carbohydrate Res. 318 1999 82 90
17. Perrier, E.; Terry, N.; Rival, D.; Coleman, A. W. Jpn. Kokai Tokkyo Koho 2001,323,002, 2001.
18. B.J. Ravoo, and R. Darcy Angew. Chem., Int. Ed. 39 2000 4324 4326
19. A. Mazzaglia, B.J. Ravoo, R. Darcy, P. Gambadauro, and F. Mallamace Langmuir 18 2002 1945 1948
20. A. Dubes, H. Parrot-Lopez, W. Abdelwahed, G. Degobert, H. Fessi, P. Shahgaldian, and A.W. Coleman Eur. J. Pharm. Biopharm. 55 2003 279 282
21. K. Tsujihara, H. Kurita, and M. Kawazu Bull. Chem. Soc. Jpn. 50 1977 1567
22. S. Lesieur, D. Charon, P. Lesieur, C. Ringard-Lefebvre, V. Muguet, D. Duchêne, and D. Wouessidjewe Chem. Phys. Lipids 106 2000 127 144
23. A. Dubes, D. Bouchu, R. Lamartine, and H. Parrot-Lopez Tetrahedron Lett. 42 2001 9147 9151
24. R. Kassab, C. Félix, H. Parrot-Lopez, and R. Bonaly Tetrahedron Lett. 38 1997 7555 7558
25. R.C. Petter, J.C. Salek, C.T. Sikorski, G. Kumaravel, and F.T. Lin J. Am. Chem. Soc. 112 1990 3860 3868
26. A. Dubes, H. Parrot-Lopez, P. Shahgaldian, and A.W. Coleman J. Colloid Interface Sci. 259 2003 103 111