Multivalency and cooperativity in supramolecular chemistry

Accounts of Chemical Research

Volumn 38, Issue 9, 2005, Pages 723-732

  Badjić, Jovica D ^a,c   Nelson, Alshakim ^a,d   Cantrill, Stuart J ^a   Turnbull, W Bruce ^b   Stoddart, J Fraser ^a,e  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF LEEDS   (United Kingdom)

^c OHIO STATE UNIVERSITY   (United States)

^d California Institute of Technology   (United States)

^e CALIFORNIA NANOSYSTEMS INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CYCLODEXTRIN DERIVATIVE; NANOMATERIAL;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; MACROMOLECULE; NANOTECHNOLOGY; THERMODYNAMICS;

BETA-CYCLODEXTRINS; MACROMOLECULAR SUBSTANCES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NANOSTRUCTURES; NANOTECHNOLOGY; THERMODYNAMICS;

EID: 26644449181     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar040223k     Document Type: Article

References (55)

1. Philp, D.; Stoddart, J. F. Self-Assembly in Natural and Unnatural Systems. Angew. Chem., Int. Ed. Engl. 1996, 35, 1155-1196.
2. Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Noncovalent Synthesis using Hydrogen Bonding. Angew. Chem., Int. Ed. 2001, 40, 2382-2426.
3. Sun, W.-Y.; Yoshizawa, M.; Kusukawa, T.; Fujita, M. MultiComponent Metal-Ligand Self-Assembly. Curr. Opin. Chem. Biol. 2002, 6, 757-764.
4. Adams, H.; Hunter, C. A.; Lawson, K. R.; Perkins, J.; Spey, S. E.; Urch, C. J.; Sanderson, J. M. A Supramolecular System for Quantifying Aromatic Stacking Interactions. Chem.-Eur. J. 2001, 7, 4863-4877.
5. Mueller-Dethlefs, K.; Hobza, P. Noncovalent Interactions: A Challenge for Experiment and Theory. Chem. Rev. 2000, 100, 143-167.
6. Fyfe, M. C. T.; Stoddart, J. F. Synthetic Supramolecular Chemistry. Acc. Chem. Res. 1997, 30, 393-401.
7. Lehn, J. M. Supramolecular Chemistry; VCH: Weinheim, Germany, 1995.
8. Elemans, J. A. A. W.; Rowan, A. E.; Nolte, R. J. M. Mastering Molecular Matter. Supramolecular Architectures by Hierarchical Self-Assembly. J. Mater. Chem. 2003, 13, 2661-2670.
9. Hamley, I. Nanotechnology With Soft Materials. Angew. Chem., Int. Ed. 2003, 42, 1692-1712.
10. Mammen, M.; Chio, S.-K.; Whitesides, G. M. Polyvalent Interactions in Biological Systems: Implications for Design and Use of Multivalent Ligands and Inhibitors. Angew. Chem., Int. Ed. 1998, 37, 2755-2794.
11. Ercolani, G. Assessment of Cooperativity in Self-Assembly. J. Am. Chem. Soc. 2003, 125, 16097-16103.
12. Lundquist, J. J.; Toone, E. J. The Cluster Glycoside Effect. Chem. Rev. 2002, 102, 555-578.
13. Lee, Y. C., Lee, R. T. Carbohydrate-Protein Interactions: Basis of Glycobiology. Acc. Chem. Res. 1995, 28, 321-327.
14. Kitov, P. I.; Bundle, D. R. On the Nature of the Multivalency Effect: A Thermodynamic Model. J. Am. Chem. Soc. 2003, 125, 16271-16284.
15. Sanders, W. J.; Gordon, E. J.; Dwir, O.; Beck, P. J.; Alon, R.; Kiessling, L. L. Inhibition of L-selectin-mediated Leukocyte Rolling by Synthetic Glycoprotein Mimics. J. Biol. Chem. 1999, 274, 5271-5278.
16. Dueren, T.; Sarkisov, L.; Yaghi, O. M.; Snurr, R. Q. Design of New Materials for Methane Storage. Langmuir 2004, 20, 2683-2689.
17. Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Artificial Molecular Machines. Angew. Chem., Int. Ed. 2000, 39, 3348-3391.
18. Flood, A. H.; Ramirez, R. J. A.; Deng, W.-Q.; Muller, R. P.; Goddard, W. A., III; Stoddart, J. F. Meccano on the Nanoscale - A Blueprint for Making Some of the World's Tiniest Machines. Aust J. Chem. 2004, 57, 301-322.
19. Breslow, R.; Belvedere, S.; Gershell, L.; Leung, D. The Chelate Effect in Binding, Catalysis, and Chemotherapy. Pure Appl. Chem. 2000, 72, 333-342.
20. Connors, K. A. Binding Constants; Wiley: New York, 1987.
21. Eaton, W. A.; Henry, E. R.; Hofrichter, J.; Mozzarelli, A. Is Cooperative Oxygen Binding by Hemoglobin Really Understood? Nat. Struct. Biol. 1999, 6, 351-358.
22. Wenz, G. Cyclodextrins as Building Blocks for Supramolecular Structures and Functional Units. Angew. Chem., Int. Ed. Engl. 1994, 33, 803-822.
23. Zhang, B.; Breslow, R. Enthalpic Domination of the Chelate Effect in Cyclodextrin Dinners. J. Am. Chem. Soc. 1993, 115, 9353-9354.
24. Jencks, W. P. On the Attribution and Additivity of Binding Energies. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 4046-4050.
25. Turnbull, W. B.; Precious, B. L.; Homans, S. W. Dissecting the Cholera Toxin-Ganglioside GM1 Interaction by Isothermal Titration Calorimetry. J. Am. Chem. Soc. 2004, 126, 1047-1054.
26. Ashton, P. R.; Campbell, P. J.; Chrystal, E. J. T.; Glink, P. T.; Menzer, S.; Philp, D.; Spencer, N.; Stoddart, J. F. Tasker, P. A.; Williams, D. J. Dialkylammonium Ion/Crown Ether Complexes: The Forerunners of a New Family of Interlocked Molecules. Angew. Chem., Int., Ed. Engl. 1995, 34, 1865-1869.
27. Chang, T.; Heiss, A. M.; Cantrill, S. J.; Fyfe, M. C. T.; Pease, A. R.; Rowan, S. J.; Stoddart, J. F.; Williams, D. J. Toward Interlocked Molecules beyond Catenanes and Rotaxanes. Org. Lett. 2000, 2, 2943-2946.
28. Gibson, H. W.; Yamaguchi, N.; Hamilton, L.; Jones, J. W. Cooperative Self-Assembly of Dendrimers via Pseudorotaxane Formation from a Homotropic Guest Molecule and Complementary Monotopic Host Dendrons. J. Am. Chem. Soc. 2002, 124, 4653-4665.
29. Balzani, V.; Clemente-León, M.; Credi, A.; Lowe, J. N.; Badjić, J. D.; Stoddart, J. F.; Williams, D. J. Controlling Multivalent Interactions in Triply-Threaded Two-Component Superbundles. Chem.-Eur. J. 2003, 9, 5348-5360.
30. Rao, J.; Lahiri, J.; Weis, R. M.; Whitesides, G. M. Design, Synthesis, and Characterization of a High-Affinity Trivalent System Derived from Vancomycin and L-Lys-D-Ala-D-Ala. J. Am. Chem. Soc. 2000, 122, 2698-2710.
31. Green, N. M. Avidin. I. The Use of Biotin-14C for Kinetic Studies and for Assay. Biochem. J. 1963, 89, 585-591.
32. Badjić, J. D.; Balzani, V.; Credi, A.; Lowe, J. N.; Silvi, S.; Stoddart, J. F. A Mechanically Interlocked Bundle. Chem.-Eur. J. 2004, 10, 1926-1935.
33. Arranz-Plaza, E.; Tracy, A. S.; Siriwardena, A.; Pierce, J. M.; Boons, G.-J. High-Avidity, Low-Affinity Multivalent Interactions and the Block to Polyspermy in Xenopus laevis. J. Am. Chem. Soc. 2002, 124, 13035-13046.
34. Templated Organic Synthesis; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1999.
35. Marvaud, V.; Vidal-Ferran, A.; Webb, S. J.; Sanders, J. K. M. Stereospecific Templated Synthesis of a Triruthenium Butadiyne-Linked Cyclic Porphyrin Trimer. J. Chem. Soc., Dalton Trans. 1997, 985-990.
36. Robertson, A.; Sinclair, A. J.; Philp, D. Minimal Self-Replicating Systems. Chem. Soc. Rev. 2000, 29, 141-152.
37. Sievers, D.; von Kiedrowski, G. Self-Replication of Hexadeoxy-nucleotide Analogues: Autocatalysis versus Cross-Catalysis. Chem.-Eur. J. 1998, 4, 629-641.
38. Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Dynamic Covalent Chemistry. Angew. Chem., Int. Ed. 2002, 41, 899-952.
39. Kilbinger, A. F. M.; Cantrill, S. J.; Waltman, A. W.; Day, M. W.; Grubbs, R. H. Magic Ring Rotaxanes by Olefin Metathesis. Angew. Chem., Int. Ed. 2003, 42, 3281-3285.
40. Badjio, J. D.; Cantrill, S. J.; Grubbs, R. H.; Guidry, E. N.; Orenes, R.; Stoddart, J. F. The Exclusivity of Multivalency in Dynamic Covalent Processes. Angew. Chem., Int. Ed. 2004, 43, 3273-3278.
41. Kryschenko, Y. K.; Seidel, S. R.; Muddiman, D. C.; Nepomuceno, A. I.; Stang, P. J. Coordination-Driven Self-Assembly of Supramolecular Cages: Heteroatom-Containing and Complementary Trigonal Prisms. J. Am. Chem. Soc. 2003, 125, 9647-9652.
42. Chichak, K. S.; Cantrill, S. J.; Pease, A. R.; Chiu, S.-H.; Cave, G. W. V.; Atwood, J. L.; Stoddart, J. F. Molecular Borromean Rings. Science 2004, 304, 1308-1312.
43. Brewer, C. F.; Miceli, M. C.; Baum, L. G. Clusters, Bundles, Arrays and Lattices: Novel Mechanisms for Lectin-Saccharide-Mediated Cellular Interactions. Curr. Opin. Struct. Biol. 2002, 12, 616-623.
44. Fiedler, D.; Leung, D. H.; Bergman, R. G.; Raymond, K. N. Enantioselective Guest Binding and Dynamic Resolution of Cationic Ruthenium Complexes by a Chiral Metal-Ligand Assembly. J. Am. Chem. Soc. 2004, 126, 3674-3675.
45. Christensen, T.; Gooden, D. M.; Kung, J. E.; Tonne, E. J. Additivity and the Physical Basis of Multivalency Effects: A Thermodynamic Investigation of the Calcium EDTA Interaction. J. Am. Chem. Soc. 2003, 125, 7357-7366.
46. Schliwa, M.; Woehlke, G. Molecular Motors. Nature 2003, 422, 759-765.
47. Badjić, J.; Balzani, V.; Credi, A.; Silvi, S.; Stoddart, J. F. A Molecular Elevator. Science 2004, 303, 1845-1849.
48. Pease, A. R.; Stoddart, J. F. Computing at the Molecular Level. Struct. Bonding 2001, 99, 189-236.
49. Huskens, J.; Deij, M. A.; Reinhoudt, D. N. Attachment of Molecules at a Molecular Printboard by Multiple Host-Guest Interactions. Angew. Chem., Int. Ed. 2002, 41, 4467-4471.
50. Auletta, T.; Dordi, B.; Mulder, A.; Sartori, A.; Onclin, S.; Bruinink, C. M.; Péter, M.; Nijhuis, C. A.; Beijleveld, H.; Schönherr, H.; Vancso, G. J.; Casnati, A.; Ungaro, R.; Ravoo, B. J.; Huskens, J.; Reinhoudt, D. N. Writing Patterns of Molecules on Molecular Printboards. Angew. Chem., Int. Ed. 2004, 43, 369-373.
51. Metallo, S. J.; Kane, R. S.; Holmlin, R. E.; Whitesides, G. M. Using Bifunctional Polymers Presenting Vancomycin and Fluorescein Groups to Direct Anti-Fluorescein Antibodies to Self-Assembled Monolayers Presenting D-Alanine-D-Alanine Groups. J. Am. Chem. Soc. 2003, 125, 4534-4540.
52. McDonald, J. C.; Whitesides, G. M. Poly(dimethylsiloxane) as a Material for Fabricating Microfluidic Devices. Acc. Chem. Res. 2002, 35, 491-499.
53. Ginger, D. S.; Zhang, H.; Mirkin, C. A. The Evolution of Dip-Pen Nanolithography. Angew. Chem., Int. Ed. 2004, 43, 30-35.
54. Huskens, J.; Mulder, A.; Auletta, T.; Nijhuis, C. A.; Ludden, M. J. W.; Reinhoudt, D. N. A Model for Describing the Thermodynamics of Multivalent Host-Guest Interactions at Interfaces. J. Am. Chem. Soc. 2004, 126, 6784-6797.
55. Mulder, A.; Huskens, J.; Reinhoudt, D. N. Multivalency in Supramolecular Chemistry and Nanofabrication. Org. Biomol. Chem. 2004, 2, 3409-3424.