Supramolecular structures based on dimeric combinations of cyclodextrin and adamantane via click chemistry

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 62, Issue 3-4, 2008, Pages 197-202

  Munteanu, Maricica ^a   Choi, Soowhan ^a   Ritter, Helmut ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Cyclodextrin and adamantane dimers; Microwave assisted cycloaddition; Supramolecular structures

Indexed keywords

EID: 55949083381     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-008-9457-x     Document Type: Article

References (37)

1. M Albrecht 2007 Supramolecular chemistry-general principles and selected examples from anion recognition and metallosupramolecular chemistry Naturwissenschaften 94 951 966
2. Rostovtsev, V.V., Green L.G., Fokin, V.V., Sharpless, K.B.: A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem. 114, 2708-2711 (2002);
3. Angew. Chem. Int. Ed 41, 2596-2599 (2002)
4. P Mobian J-P Collin J-P Sauvage 2006 Efficient synthesis of a labile copper(I)-rotaxane complex using click chemistry Tetrahedron Lett. 47 4907 4909
5. S Chittaboina F Xie Q Wang 2005 One-pot synthesis of triazole-linked glycoconjugates Tetrahedron Lett. 46 2331 2336
6. F Perez-Balderas M Ortega-Munoz J Morales-Sanfrutos F Hernandez-Mateo FG Calvo-Flores JA Calvo-Asin J Isac-Garcia F Santoyo-Gonzalez 2003 Multivalent neoglycoconjugates by regiospecific cycloaddition of alkynes and azides using organic-soluble copper catalysts Org. Lett. 5 1951 1954
7. M Ortega-Muñoz J Morales-Sanfrutos F Perez-Balderas F Hernandez-Mateo MD Giron-Gonzalez N Sevillano-Tripero R Salto-Gonzalez F Santoyo-Gonzalez 2007 Click multivalent neoglycoconjugates as synthetic activators in cell adhesion and stimulation of monocyte/machrophage cell lines Org. Biomol.Chem. 5 2291 2301
8. TR Chan R Hilgraf KB Sharpless VV Fokin 2004 Polytriazoles as copper(i)-stabilizing ligands in catalysis Org. Lett. 6 2853
9. Hoogenboom, R., Moore, B.C., Schubert U.S.: Synthesis of star-shaped poly(epsilon-caprolactone) via 'click' chemistry and 'supramolecular click' chemistry. Chem. Commun. 4010-4012 (2006)
10. R Breinbauer M Köhn 2003 Azide-alkyne coupling: a powerful reaction for bioconjugate chemistry ChemBioChem 4 1147 1149
11. JE Moses AD Moorhouse 2007 The growing applications of click chemistry Chem. Soc. Rev. 36 1249 1262
12. Gupta, S.S., Raja, K.S., Eiton, K.S., Kaltgrad, E., Strable, E., Finn, M.G.: Virus-glycopolymer conjugates by copper (I) catalysis of atom transfer radical polymerization and azide-alkyne cycloaddition. Chem. Commun. 4315-4317 (2005)
13. Q Wang TR Chan R Hilgraf V Fokin KB Sharpless MG Finn 2003 Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition J. Am. Chem. Soc. 125 3192 3193
14. HC Kolb B Sharpless 2003 The growing impact of click chemistry on drug discovery Drug Discovery Today 8 24
15. DD Diaz S Punna P Holzer AK McPherson KB Sharpless VV Kokin MG Finn 2004 Click chemistry in materials synthesis. 1. Adhesive polymers from copper-catalyzed azide-alkyne cycloaddition J. Polym. Sci.: Part A: Polym. Chem. 42 4392 4403
16. WH Binder R Sachsenhofer 2007 Click chemistry in polymer and materials science Macromol. Rapid Commun. 28 15 54
17. J-F Lutz HG Borner K Weichnehan 2007 Combining ATRP and "click" chemistry: a promising platform toward functional biocompatible polymers and polymer bioconjugates Macromolecules 39 6376 6383
18. R Villalonga R Cao A Fragoso 2007 Supramolecular chemistry of cyclodextrins in enzyme technology Chem. Rev. 107 308 311
19. C Easton 2005 Cyclodextrin-based catalysts and molecular reactors J. Pure Appl. Chem. 77 1865 1871
20. J Storsberg H Ritter H Pielartzik L Groenendaal 2000 Cyclodextrins in polymer synthesis: supramolecular cyclodextrin complexes of pyrrole and 3, 4-ethylenedioxythiophene and their oxidative polymerization Adv. Mater. 12 567 569
21. Choi, S., Ritter, H.: Novel polymerization of myrcene in aqueous media via cyclodextrin-complexes. e-Polymers no. 045 (2007)
22. A Harada 2006 Supramolecular polymers based on cyclodextrins J. Polym. Sci.: Part A: Polym. Chem. 44 5113 5119
23. R Breslow N Greenspoon T Guo R Zarzycki 1989 Very strong binding of appropriate substrates by cyclodextrin dimers J. Am. Chem. Soc. 111 8296 8297
24. B Zhang R Breslow 1993 Enthalpic domination of the chelate effect in cyclodextrin dimers J. Am. Chem. Soc. 115 9353 9354
25. R Breslow S Halfon B Zhang 1995 Molecular recognition by cyclodextrin dimers Tetrahedron 51 377 388
26. R Breslow B Zhang 1996 Cholesterol recognition and binding by cyclodextrin dimers J. Am. Chem. Soc. 118 8495 8496
27. Leung, D.K., Yang, Z., Breslow, R.: Selective disruption of protein aggregation by cyclodextrin dimers. Proc. Natl. Acad. Sci. USA 97, 5050-5053 (2000)
28. R Breslow S Belvedere L Gershell D Leung 2000 The chelate effect in binding, catalysis, and chemotherapy. Pure Appl. Chem. 72 333 342
29. SPD Baugh Z Yang DK Leung DM Wilson R Breslow 2001 Cyclodextrin dimers as cleavable carriers of photodynamic sensitizers J. Am. Chem. Soc. 123 12488 12494
30. Moore, S.: Askew J. A., Gibson, G.L., Aborgrein, A., El-Agnaf, O., Allsop, D., Leung, D.K, Breslow, R.: Novel cyclodextrin dimers and trimers as inhibitors of amyloid peptide aggregation. Neurobiol. Aging 23, S105-S397 (2002)
31. D Wilson L Perlson R Breslow 2003 Helical templating of oligopeptides by cyclodextrin dimers Bioorg. Med. Chem. 11 2649 2653
32. O Bistri K Mazeau R Auzely-Velty M Sollogoub 2007 A hydrophilic cyclodextrin duplex forming supramolecular assemblies by physical cross-linking of a biopolymer Chem. Eur. J. 13 8847 8857
33. O Kretschmann C Steffens H Ritter 2007 Cyclodextrin complexes of polymers bearing adamantyl groups: host-guest interactions and the effect of spacers on water solubility Angew. Chem. Int. Ed. 46 2708
34. O Kretschmann SW Choi M Miyauchi I Tomatsu A Harada H Ritter 2006 Switchable hydrogels obtained by supramolecular cross-linking of adamantyl-containing LCST copolymers with cyclodextrin dimers Angew. Chem. Int. Ed. 45 4361 4361
35. K. Ohga Y. Takashima H. Takahashi Y. Kawaguchi H. Yamaguchi A. Harada 2005 Preparation of supramolecular polymers from a cyclodextrin dimer and ditopic guest molecules: control of structure by linker flexibility Macromolecules 38 5897
36. M Bonini S Rossi G Karlson M Almgren P Lo Nostro P Baglioni 2006 Self-assembly of β-cyclodextrin in water. Part 1: Cryo-TEM and dynamic and static light scattering Langmuir 22 1478 1484
37. S Rossi M Bonini P Bonini P Baglioni 2007 Self-assembly of β-cyclodextrin in water. 2. Electron spin resonance Langmuir 23 10959 10967