Threading cyclodextrins in chloroform: A [2]pseudorotaxane

International Journal of Molecular Sciences

Volumn 8, Issue 10, 2007, Pages 1052-1063

  Gattuso, Giuseppe ^a   Gargiulli, Claudia ^a   Parisi, Melchiorre F ^a  

^a UNIVERSITY OF MESSINA   (Italy)

Author keywords

Cyclodextrin; Pseudorotaxane; Supramolecular chemistry; Viologen

Indexed keywords

CHLOROFORM; CYCLODEXTRIN; HEPTAKIS 2,6 DI O METHYL 3 O ACETYL BETA CYCLODEXTRIN; PSEUDOROTAXANE; UNCLASSIFIED DRUG; VIOLOGEN;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; COMPLEX FORMATION; PROTON NUCLEAR MAGNETIC RESONANCE; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 36049002394     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/i8101052     Document Type: Article

References (44)

1. Armspach, D.; Gattuso, G.; Koeniger, R.; Stoddart, J. F. In Bioorganic Chemistry: Carbohydrates; Hecht, S.M., Ed.; Oxford University Press: New York, 1999; pp. 458-488, 597-602.
2. Szejtli, J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 1998, 98, 1743-1754.
3. Comprehensive Supramolecular Chemistry: Cyclodextrins; Szejtli, J.; Osa, T., Eds.; Elsevier: Oxford, 1996; Vol. 3.
4. Hedges, A.R. Industrial applications of cyclodextrins. Chem. Rev. 1998, 98 , 2035-2044.
5. Del Valle, E.M.M. Cyclodextrins and their uses: a review. Process Biochem. 2004, 39, 1033-1046.
6. Uekama, K.; Hirayama, F.; Irie, T. Cyclodextrin drug carrier systems. Chem. Rev. 1998, 98, 2045-2076.
7. Szente, L.; Szejtli, J. Highly soluble cyclodextrin derivatives: chemistry, properties, and trends in development. Adv. Drug Deliver. Rev. 1999, 36, 17-28.
8. Stoddart, J.F. Cyclodextrins, off-the-shelf components for the construction of mechanically interlocked molecular-systems. Angew. Chem., Int. Ed. Engl. 1992, 31, 846-848.
9. Wenz, G. Cyclodextrins as building-blocks for supramolecular structures and functional units. Angew. Chem., Int. Ed. Engl. 1994, 33, 803-822.
10. Wenz, G.; Han, B.H.; Muller, A. Cyclodextrin rotaxanes and polyrotaxanes. Chem. Rev. 2006 106, 782-817.
11. Harada, A. Cyclodextrin-based molecular machines. Acc. Chem. Res. 2001, 34, 456-464.
12. Nepogodiev, S.A.; Stoddart, J.F. Cyclodextrin-based catenanes and rotaxanes. Chem. Rev. 1998, 98, 1959-1976.
13. Onagi, H.; Blake, C.J.; Easton, C.J.; Lincoln, S.F. Installation of a ratchet tooth and pawl to restrict rotation in a cyclodextrin rotaxane. Chem. Eur. J. 2003, 9, 5978-5988.
14. Stanier, C.A.; Alderman, S.J.; Claridge, T.D.W.; Anderson, H.L. Unidirectional photoinduced shuttling in a rotaxane with a symmetric stilbene dumbbell. Angew. Chem. Int. Ed. 2002, 41, 1769-1772.
15. Armspach, D.; Ashton, P.R.; Ballardini, R.; Balzani, V.; Godi, A.; Moore, C.P.; Prodi, L.; Spencer, N; Stoddart, J.F.; Tolley, M.S.; Wear, T.J.; Williams, D.J. Catenated cyclodextrins. Chem. Eur. J. 1995, 1, 33-55.
16. Harada, A.; Hashidzume, A.; Takashima, Y. Cyclodextrin-based supramolecular polymers. Polym. Sci. 2006, 201, 1-43.
17. Suh, J. Synthetic artificial peptidases and nucleases using macromolecular catalytic systems. Acc. Chem. Res. 2003, 36, 562-570.
18. Breslow, R.; Dong, S.D. Biomimetic reactions catalyzed by cyclodextrins and their derivatives. Chem. Rev. 1998, 98, 1997-2012.
19. Saha, S.; Stoddart J.F. Photo-driven molecular devices. Chem. Soc. Rev. 2007, 36, 77-92.
20. Tian H.; Wang Q.C. Recent progress on switchable rotaxanes. Chem. Soc. Rev. 2006, 35, 361-374.
21. Mirzoian, A.; Kaifer, A.E. Reactive pseudorotaxanes: Inclusion complexation of reduced viologens by the hosts β-cyclodextrin and heptakis(2,6-di-O-methyl)-β-cyclodextrin. Chem. Eur. J. 1997, 3, 1052-1058.
22. Murakami, M.; Kawabuchi, A.; Matsumoto, R.; Ido, T.; Nakashima, N. A multi-mode-driven molecular shuttle: photochemically and thermally reactive azobenzene rotaxanes. J. Am. Chem. Soc. 2005, 127, 15891-15899.
23. Murakami, M.; Kawabuchi, A.; Kotoo, K.; Kunitake, M.; Nakashima, N. A light-driven molecular shuttle based on a rotaxane. J. Am. Chem. Soc. 1997, 119, 7605-7606.
24. Ma, X.; Wang, Q.C.; Qu, D.H.; Xu, Y.; Ji, F.Y.; Tian, H. A light-driven pseudo[4]rotaxane encoded by induced circular dichroism in a hydrogel. Adv. Funct. Mater. 2007, 17, 829-837.
25. Liu, Y.; Li, X.-Y.; Zhang, H.-Y.; Li, C.-J.; Ding, F. Cyclodextrin-driven movement of cucurbit[7]uril. J. Org. Chem. 2007, 72, 3640-3645.
26. Saenger, W. In Inclusion Compounds; Atwood, J.L.; Davies, J.E.D.; MacNicol, D.D., Eds.; Academic Press: London, 1984; Vol. 2, pp. 231-259.
27. Engeldinger, E.; Armspach, D.; Matt, D. Capped cyclodextrins. Chem. Rev. 2003, 103, 4147-4173.
28. Rauf Khan, A.; Forgo, P.; Stine, K.J.; D'Souza, V.T. Methods for selective modifications of cyclodextrins. Chem. Rev. 1998, 98, 1977-1996.
29. Ashton, P.R.; Boyd, S. E.; Gattuso, G.; Hartwell, E. Y.; Koeniger, R.; Spencer, N.; Stoddart, J. F. A novel approach to the synthesis of some chemically-modified cyclodextrins. J. Org. Chem. 1995, 60, 3898-3903.
30. Morozumi, T.; Sato, N.; Nakamura H. Selective pseudo-rotaxane type complex formation of zinc(II) (t-butylatedtetraphenyl) porphyrin-viologen linked compounds with tri-O-methyl-β-cyclodextrin. J. Incl. Phenom. Macro. 2006, 56, 141-148.
31. Wenz, G.; Wolf, F.; Wagner, M.; Kubik, S. Topology and molecular chemistry - synthesis, topography and stability of a [2]-rotaxane derived from a lipophilic cyclodextrin derivative. New J. Chem. 1993, 17, 729-738.
32. Wenz, G.; Vonderbey, E.; Schmidt, L. Synthesis of a lipophilic cyclodextrin-[2]-rotaxane. Angew. Chem., Int. Ed. Engl. 1992, 31, 783-785.
33. Sliwa, W.; Bachowska, B. Supramolecular species bearing quaternary azaaromatic moieties. Heterocycles 2006, 68, 1467-1500.
34. Cafeo, G.; Gargiulli, C.; Gattuso, G.; Kohnke, F.H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M.F. Recognition and binding of paraquat dichloride by cyclodextrin/calix[6]pyrrole binary host systems. Tetrahedron Lett. 2002, 43, 8103-8106.
35. Cafeo, G.; Gattuso, G.; Kohnke, F.H.; Notti, A.; Occhipinti, S.; Pappalardo, S.; Parisi, M.F. Remarkable boosting of the binding of ion-paired organic salts by binary host systems. Angew. Chem. Int. Ed. 2002, 41, 2122-2126.
36. Giastas, P.; Mourtzis, N.; Yannakopoulou, K.; Mavridis I.M. Pseudorotaxanes of β-cyclodextrin with diamino end-functionalized oligo-phenyl and -benzyl compounds in solution and in the solid state. J. Incl. Phenom. Macro. 2002, 44, 247-250.
37. Park, J.W.; Song, H.J.; Chang, H.J. Unidirectional α-cyclodextrin- based [2]rotaxanes bearing viologen unit on axle. Tetrahedron Lett. 2006, 47, 3831-3834.
38. Oshikiri, T.; Takashima, Y.; Yamaguchi, H.; Harada A. Kinetic control of threading of cyclodextrins onto axle molecules. J. Am. Chem. Soc. 2005, 127, 12186-12187.
39. Park, J.W.; Song H.J. Isomeric [2]rotaxanes and unidirectional [2]pseudorotaxane composed of α-cyclodextrin and aliphatic chain-linked carbazole-viologen compounds. Org. Lett. 2004, 6, 4869-4872.
40. Baer, A.J.; Macartney, D.H. Orientational isomers of α-cyclodextrin [2]semi-rotaxanes with asymmetric dicationic threads. Org. Biomol. Chem. 2005, 3, 1448-1452.
41. Park, J.W.; Song H.J.; Lee, S.Y. Face selectivity of inclusion complexation of viologens with β-cyclodextrin and 6-O-(2-sulfonato- 6-naphthyl)-β-cyclodextrin. J. Phys. Chem. B 2002, 106, 7186-7192.
42. Cyclodextrin 1 was prepared according to a literature procedure and its spectroscopic data were in full agreement with those previously published. See: Hirayama, F.; Mieda, S.; Miyamoto, Y.; Arima, H.; Uekama, K. Heptakis(2,6-di-O-methyl-3-O-acetyl)-β-cyclodextrin: a water-soluble cyclodextrin derivative with low hemolytic activity. J. Pharm. Sci. 1999, 88, 970-975.
43. Alston, D.R.; Lilley, T.H.; Stoddart, J.F. The binding of cyclobutane-1,1-dicarboxylatodiamineplatinum(II) by α-cyclodextrin in aqueous solution. J. Chem. Soc. Chem. Commun. 1985, 1600-1602.
44. Perrin, D.D.; Armarego, W.L.F. Purification of Laboratory Chemicals, Pergamon Press: Oxford, 1989.