Stimuli responsive systems constructed using cucurbit[ n ]uril-type molecular containers

Accounts of Chemical Research

Volumn 47, Issue 7, 2014, Pages 2052-2062

  Isaacs, Lyle ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZO COMPOUND; AZOBENZENE; CARBON DIOXIDE; GLYCOLURIL; IMIDAZOLE DERIVATIVE; NANOPARTICLE; NEUROMUSCULAR BLOCKING AGENT; WATER;

ANIMAL; ANTAGONISTS AND INHIBITORS; BOVINE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; DRUG DELIVERY SYSTEM; DRUG EFFECTS; HYDROGEN BOND; ISOMERISM; MCF 7 CELL LINE; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; RAT; THERMODYNAMICS; TOXICITY TESTING; X RAY CRYSTALLOGRAPHY;

ALKYNES; ANIMALS; AZO COMPOUNDS; CARBON DIOXIDE; CATALYSIS; CATTLE; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; DRUG DELIVERY SYSTEMS; HYDROGEN BONDING; HYDROGEN-ION CONCENTRATION; IMIDAZOLES; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MCF-7 CELLS; MOLECULAR STRUCTURE; NANOPARTICLES; NEUROMUSCULAR BLOCKING AGENTS; RATS; THERMODYNAMICS; TOXICITY TESTS; WATER;

EID: 84904429582     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar500075g     Document Type: Article

References (39)

1. Kramer, R.; Lehn, J.-M.; Marquis-Rigault, A. Self-Recognition in Helicate Self-Assembly: Spontaneous Formation of Helical Metal Complexes from Mixtures of Ligands and Metal Ions Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5394-5398
2. Rowan, S. J.; Hamilton, D. G.; Brady, P. A.; Sanders, J. K. M. Automated Recognition, Sorting, and Covalent Self-Assembly by Predisposed Building Blocks in a Mixture J. Am. Chem. Soc. 1997, 119, 2578-2579
3. Freeman, W. A.; Mock, W. L.; Shih, N.-Y. Cucurbituril J. Am. Chem. Soc. 1981, 103, 7367-7368
4. Rowan, A. E.; Elemans, J. A. A. W.; Nolte, R. J. M. Molecular and Supramolecular Objects from Glycoluril Acc. Chem. Res. 1999, 32, 995-1006
5. Rebek, J., Jr. Reversible Encapsulation and Its Consequences in Solution Acc. Chem. Res. 1999, 32, 278-286
6. Kim, J.; Jung, I.-S.; Kim, S.-Y.; Lee, E.; Kang, J.-K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. New Cucurbituril Homologues: Syntheses, Isolation, Characterization, and X-ray Crystal Structures of Cucurbit[ n ]uril (n = 5, 7, and 8) J. Am. Chem. Soc. 2000, 122, 540-541
7. Day, A.; Arnold, A. P.; Blanch, R. J.; Snushall, B. Controlling Factors in the Synthesis of Cucurbituril and Its Homologues J. Org. Chem. 2001, 66, 8094-8100
8. Liu, S.; Zavalij, P. Y.; Isaacs, L. Cucurbit[10]uril J. Am. Chem. Soc. 2005, 127, 16798-16799
9. Masson, E.; Ling, X.; Joseph, R.; Kyeremeh-Mensah, L.; Lu, X. Cucurbituril Chemistry: A Tale of Supramolecular Success RSC Adv. 2012, 2, 1213-1247
10. Isaacs, L. The Mechanism of Cucurbituril Formation Isr. J. Chem. 2011, 51, 578-591
11. Lucas, D.; Minami, T.; Iannuzzi, G.; Cao, L.; Wittenberg, J. B.; Anzenbacher, P.; Isaacs, L. Templated Synthesis of Glycoluril Hexamer and Monofunctionalized Cucurbit[6]uril Derivatives J. Am. Chem. Soc. 2011, 133, 17966-17976
12. Wu, A.; Chakraborty, A.; Fettinger, J. C.; Flowers, R. A., II; Isaacs, L. Molecular clips that undergo heterochiral aggregation and self-sorting Angew. Chem., Int. Ed. 2002, 41, 4028-4031
13. Ghosh, S.; Wu, A.; Fettinger, J. C.; Zavalij, P. Y.; Isaacs, L. Self-Sorting Molecular Clips J. Org. Chem. 2008, 73, 5915-5925
14. Wu, A.; Isaacs, L. Self-Sorting: The Exception or the Rule? J. Am. Chem. Soc. 2003, 125, 4831-4835
15. Mukhopadhyay, P.; Wu, A.; Isaacs, L. Social Self-Sorting in Aqueous Solution J. Org. Chem. 2004, 69, 6157-6164
16. Mock, W. L.; Shih, N. Y. Structure and Selectivity in Host-Guest Complexes of Cucurbituril J. Org. Chem. 1986, 51, 4440-4446
17. Liu, S.; Ruspic, C.; Mukhopadhyay, P.; Chakrabarti, S.; Zavalij, P. Y.; Isaacs, L. The Cucurbit[ n ]uril Family: Prime Components for Self-Sorting Systems J. Am. Chem. Soc. 2005, 127, 15959-15967
18. Jeon, W. S.; Moon, K.; Park, S. H.; Chun, H.; Ko, Y. H.; Lee, J. Y.; Lee, E. S.; Samal, S.; Selvapalam, N.; Rekharsky, M. V.; Sindelar, V.; Sobransingh, D.; Inoue, Y.; Kaifer, A. E.; Kim, K. Complexation of Ferrocene Derivatives by the Cucurbit[7]uril Host: A Comparative Study of the Cucurbituril and Cyclodextrin Host Families J. Am. Chem. Soc. 2005, 127, 12984-12989
19. Biedermann, F.; Uzunova, V. D.; Scherman, O. A.; Nau, W. M.; De Simone, A. Release of High-Energy Water as an Essential Driving Force for the High-Affinity Binding of Cucurbit[ n ]urils J. Am. Chem. Soc. 2012, 134, 15318-15323
20. Rekharsky, M. V.; Mori, T.; Yang, C.; Ko, Y. H.; Selvapalam, N.; Kim, H.; Sobransingh, D.; Kaifer, A. E.; Liu, S.; Isaacs, L.; Chen, W.; Moghaddam, S.; Gilson, M. K.; Kim, K.; Inoue, Y. A Synthetic Host-Guest System Achieves Avidin-Biotin Affinity by Overcoming Enthalpy-Entropy Compensation Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 20737-20742
21. Moghaddam, S.; Yang, C.; Rekharsky, M.; Ko, Y. H.; Kim, K.; Inoue, Y.; Gilson, M. K. New Ultrahigh Affinity Host-Guest Complexes of Cucurbit[7]uril with Bicyclo[2.2.2]octane and Adamantane Guests: Thermodynamic Analysis and Evaluation of M2 Affinity Calculations J. Am. Chem. Soc. 2011, 133, 3570-3581
22. Kaifer, A. E.; Li, W.; Yi, S. Cucurbiturils as Versatile Receptors for Redox Active Substrates Isr. J. Chem. 2011, 51, 496-505
23. Cao, L.; Sekutor, M.; Zavalij, P. Y.; Mlinaric-Majerski, K.; Glaser, R.; Isaacs, L. Cucurbit[7]uril·Guest Pair with an Attomolar Dissociation Constant Angew. Chem., Int. Ed. 2014, 53, 988-993
24. Huang, W.-H.; Liu, S.; Zavalij, P. Y.; Isaacs, L. Nor-Seco-Cucurbit[10] uril Exhibits Homotropic Allosterism J. Am. Chem. Soc. 2006, 128, 14744-14745
25. Chakrabarti, S.; Mukhopadhyay, P.; Lin, S.; Isaacs, L. Reconfigurable Four-Component Molecular Switch Based on pH-Controlled Guest Swapping Org. Lett. 2007, 9, 2349-2352
26. Wu, J.; Isaacs, L. Cucurbit[7]uril Complexation Drives Thermal trans-cis-Azobenzene Isomerization and Enables Colorimetric Amine Detection Chem.-Eur. J. 2009, 15, 11675-11680
27. Nau, W. M.; Florea, M.; Assaf, K. I. Deep Inside Cucurbiturils: Physical Properties and Volumes of their Inner Cavity Determine the Hydrophobic Driving Force for Host-Guest Complexation Isr. J. Chem. 2011, 51, 559-577
28. Pluth, M.; Bergman, R.; Raymond, K. Proton-Mediated Chemistry and Catalysis in a Self-Assembled Supramolecular Host Acc. Chem. Res. 2009, 42, 1650-1659
29. Liu, S.; Zavalij, P. Y.; Lam, Y.-F.; Isaacs, L. Refolding Foldamers: Triazene-Arylene Oligomers That Change Shape with Chemical Stimuli J. Am. Chem. Soc. 2007, 129, 11232-11241
30. Huang, W.-H.; Zavalij, P. Y.; Isaacs, L. Metal-Ion-Induced Folding and Dimerization of a Glycoluril Decamer in Water Org. Lett. 2009, 11, 3918-3921
31. Wittenberg, J. B.; Zavalij, P. Y.; Isaacs, L. Supramolecular Ladders from Dimeric Cucurbit[6]uril Angew. Chem., Int. Ed. 2013, 52, 3690-3694
32. Ghosh, S.; Isaacs, L. Biological Catalysis Regulated by Cucurbit[7]uril Molecular Containers J. Am. Chem. Soc. 2010, 132, 4445-4454
33. Kim, C.; Agasti, S. S.; Zhu, Z.; Isaacs, L.; Rotello, V. M. Recognition-Mediated Activation of Therapeutic Gold Nanoparticles Inside Living Cells Nat. Chem. 2010, 2, 962-966
34. Ma, D.; Hettiarachchi, G.; Nguyen, D.; Zhang, B.; Wittenberg, J. B.; Zavalij, P. Y.; Briken, V.; Isaacs, L. Acyclic Cucurbit[n]uril Molecular Containers Enhance the Solubility and Bioactivity of Poorly Soluble Pharmaceuticals Nat. Chem. 2012, 4, 503-510
35. Vinciguerra, B.; Cao, L.; Cannon, J. R.; Zavalij, P. Y.; Fenselau, C.; Isaacs, L. Synthesis and Self-Assembly Processes of Monofunctionalized Cucurbit[7]uril J. Am. Chem. Soc. 2012, 134, 13133-13140
36. Cao, L.; Hettiarachchi, G.; Briken, V.; Isaacs, L. Cucurbit[7]uril Containers for Targeted Delivery of Oxaliplatin to Cancer Cells Angew. Chem., Int. Ed. 2013, 52, 12033-12037
37. Bom, A.; Bradley, M.; Cameron, K.; Clark, J.; Van Egmond, J.; Feilden, H.; MacLean, E.; Muir, A.; Palin, R.; Rees, D.; Zhang, M.-Q. A Novel Concept of Reversing Neuromuscular Block: Chemical Encapsulation of Rocuronium Bromide by a Cyclodextrin-Based Synthetic Host Angew. Chem., Int. Ed. 2002, 41, 266-270
38. Ma, D.; Zhang, B.; Hoffmann, U.; Sundrup, M. G.; Eikermann, M.; Isaacs, L. Acyclic Cucurbit[n]uril-Type Molecular Containers Bind Neuromuscular Blocking Agents in Vitro and Reverse Neuromuscular Block in Vivo Angew. Chem., Int. Ed. 2012, 51, 11358-11362
39. Hoffmann, U.; Grosse-Sundrup, M.; Eikermann-Haerter, K.; Zaremba, S.; Ayata, C.; Zhang, B.; Ma, D.; Isaacs, L.; Eikermann, M. Calabadion: A New Agent to Reverse the Effects of Benzylisoquinoline and Steroidal Neuromuscular- blocking Agents Anesthesiology 2013, 119, 317-325