Guest binding dynamics with cucurbit[7]uril in the presence of cations

Journal of the American Chemical Society

Volumn 133, Issue 50, 2011, Pages 20623-20633

  Tang, Hao ^a   Fuentealba, Denis ^a   Ko, Young Ho ^b   Selvapalam, Narayanan ^b   Kim, Kimoon ^b   Bohne, Cornelia ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

^b Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ASSOCIATION RATE CONSTANTS; BINDING DYNAMICS; BINDING ISOTHERMS; COMPETITIVE BINDING; CUCURBIT[7]URIL; DIFFUSION-CONTROLLED PROCESS; DISSOCIATION RATE CONSTANT; KINETIC STUDY; POSITIVELY CHARGED; STOPPED FLOW EXPERIMENTS;

DISSOCIATION; EQUILIBRIUM CONSTANTS; KINETICS; NAPHTHALENE; RATE CONSTANTS;

POSITIVE IONS;

CATION; CUCURBIT[7]URIL; HYDRONIUM ION; SODIUM; TERPENOID; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DIFFUSION; DYNAMICS; EQUILIBRIUM CONSTANT; FLUORESCENCE; KINETICS; RADIOASSAY;

EID: 83755170822     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja209266x     Document Type: Article

References (95)

1. Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844
2. Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Acc. Chem. Res. 2003, 36, 621
3. 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. J. Am. Chem. Soc. 2005, 127, 12984
4. Liu, S.; Ruspic, C.; Mukhopadhyay, P.; Chakrabarti, S.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 15959
5. 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. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 20737
6. Moghaddam, S.; Yang, C.; Rekharsky, M.; Ko, Y. H.; Kim, K.; Inoue, Y.; Gilson, M. K. J. Am. Chem. Soc. 2011, 133, 3570
7. Kim, Y.; Kim, H.; Ko, Y. H.; Selvapalam, N.; Rekharsky, M. V.; Inoue, Y.; Kim, K. Chem.-Eur. J. 2009, 15, 6143
8. Ko, Y. H.; Hwang, I.; Lee, D.-W.; Kim, K. Isr. J. Chem. 2011, 51, 506
9. Behrend, R.; Meyer, E.; Rusche, F. Justus Liebigs Ann. Chem. 1905, 339, 1
10. Mock, W. L.; Irra, T. A.; Wepsiec, J. P.; Manimaran, T. L. J. Org. Chem. 1983, 48, 3618
11. Mock, W. L.; Shih, N. Y. J. Org. Chem. 1986, 51, 4440
12. Mock, W. L.; Shih, N. Y. J. Am. Chem. Soc. 1989, 111, 2697
13. Kim, J.; Jung, I.-S.; Kim, S.-Y.; Lee, E.; Kang, J.-K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2000, 122, 540
14. Day, A.; Arnold, A. P.; Blanch, R. J.; Snushall, B. J. Org. Chem. 2001, 66, 8094
15. Mukhopadhyay, P.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2006, 128, 14093
16. Rekharsky, M. V.; Yamamura, H.; Ko, Y. H.; Selvapalam, N.; Kim, K.; Inoue, Y. Chem. Commun. 2008, 2236
17. Jiang, W. J.; Wang, Q.; Linder, O.; Klautzsch, F.; Schalley, C. A. Chem.-Eur. J. 2011, 17, 2344
18. Krasia, T. C.; Steinke, J. H. G. Chem. Commun. 2002, 22
19. Pattabiraman, M.; Natarajan, A.; Kaliappan, R.; Mague, J. T.; Ramamurthy, V. Chem. Commun. 2005, 4542
20. Wang, R.; Yuan, L.; Macartney, D. H. J. Org. Chem. 2006, 71, 1237
21. Hang, C.; Fang-fang, Z.; Jian-xin, Z.; Xi, Z.; Zhu, T.; Sai-feng, X.; Qian-jiang, Z. Catal. Commun. 2009, 11, 167
22. Basilio, N.; Garcia-Rio, L.; Moreira, J. A.; Pessego, M. J. Org. Chem. 2010, 75, 848
23. Koner, A. L.; Márquez, C.; Dickman, M. H.; Nau, W. M. Angew. Chem., Int. Ed. 2011, 50, 545
24. Pemberton, B. C.; Barooach, N.; Sribatsava, D. K.; Sivaguru, J. Chem. Commun. 2010, 46, 225
25. Parvari, G.; Reany, O.; Keinan, E. Isr. J. Chem. 2011, 51, 646
26. Lim, S.; Kim, H.; Selvapalam, N.; Kim, K.-J.; June Cho, S.; Seo, J. G.; Kim, K. Angew. Chem., Int. Ed. 2008, 47, 3352
27. Hennig, A.; Bakirci, H.; Nau, W. M. Nat. Methods 2007, 4, 629
28. Bailey, D. M.; Hennig, A.; Uzunova, V. D.; Nau, W. M. Chem.-Eur. J. 2008, 14, 6069
29. Ghale, G.; Ramalingam, V.; Urbach, A. R.; Nau, W. M. J. Am. Chem. Soc. 2011, 133, 7528
30. Lee, D.-W.; Park, K. M.; Banerjee, M.; Ha, S. H.; Lee, T.; Suh, K.; Paul, S.; Jung, H.; Kim, J.; Selvapalam, N.; Ryu, S. H.; Kim, K. Nat. Chem. 2011, 3, 154
31. Appel, E. A.; Biedermann, F.; Rauwald, U.; Jones, S. T.; Zayed, J. M.; Scherman, O. A. J. Am. Chem. Soc. 2010, 132, 14251
32. Freitag, M.; Galoppini, E. Langmuir 2010, 26, 8262
33. Gadde, S.; Batchelor, E. K.; Weiss, J. P.; Ling, Y.; Kaifer, A. E. J. Am. Chem. Soc. 2008, 130, 17114
34. Das, D.; Scherman, O. A. Isr. J. Chem. 2011, 51, 537
35. Wheate, N. J.; Day, A. I.; Blanch, R. J.; Arnold, A. P.; Cullinane, C.; Collins, G. Chem. Commun. 2004, 1424
36. Kim, K.; Selvapalam, N.; Ko, Y. H.; Park, K. M.; Kim, D.; Kim, J. Chem. Soc. Rev. 2007, 36, 267
37. Park, K. M.; Suh, K.; Jung, H.; Lee, D.-W.; Ahn, Y.; Kim, J.; Baek, K.; Kim, K. Chem. Commun. 2009, 71
38. Montes-Navajas, P.; González-Béjar, M.; Scaiano, J. C.; Garcia, H. Photochem. Photobiol. Sci. 2009, 8, 1743
39. Wyman, I. W.; Macartney, D. H. Org. Biomol. Chem. 2009, 8, 247
40. Kim, S. K.; Park, K. M.; Singha, K.; Kim, J.; Ahn, Y.; Kim, K.; Kim, W. J. Chem. Commun. 2010, 46, 692
41. Hettiarachchi, G.; Nguyen, D.; Wu, J.; Lucas, D.; Ma, D.; Isaacs, L.; Briken, V. PLoS One 2010, 5, e10514
42. Uzunova, V. D.; Cullinane, C.; Brix, K.; Nau, W. M.; Day, A. I. Org. Biomol. Chem. 2010, 8, 2037
43. McInnes, F. J.; Anthony, N. G.; Kenndy, A. R.; Wheate, N. J. Org. Biomol. Chem. 2010, 8, 765
44. Koner, A. L.; Ghosh, I.; Saleh, N.; Nau, W. M. Can. J. Chem. 2011, 89, 139
45. Macartney, D. H. Isr. J. Chem. 2011, 51, 600
46. Walker, S.; Oun, R.; McInees, F. J.; Wheate, N. J. Isr. J. Chem. 2011, 51, 616
47. Houk, K. N.; Leach, A. G.; Kim, S. P.; Zhang, X. Angew. Chem., Int. Ed. 2003, 42, 4872
48. Moghaddam, S.; Inoue, Y.; Gilson, M. K. J. Am. Chem. Soc. 2009, 131, 4012
49. Connors, K. A. J. Pharm. Sci. 1995, 84, 843
50. Connors, K. A. Chem. Rev. 1997, 97, 1325
51. Bohne, C. Langmuir 2006, 22, 9100
52. Bohne, C. In Supramolecular Photochemistry: Controlling Photochemical Processes; Ramamurthy, V.; Inoue, Y., Eds.; John Wiley & Sons: Singapore, 2011, p 1.
53. Kleinman, M. H.; Bohne, C. In Molecular and Supramolecular Photochemistry; Ramamurthy, V.; Schanze, K. S., Eds.; Marcel Dekker Inc.: New York, 1997; Vol. 1, p 391.
54. Marquez, C.; Nau, W. M. Angew. Chem., Int. Ed. 2001, 40, 3155
55. Hoffmann, R.; Knoche, W.; Fenn, C.; Buschmann, H.-J. J. Chem. Soc., Faraday Trans. 1994, 90, 1507
56. Marquez, C.; Hudgins, R. R.; Nau, W. M. J. Am. Chem. Soc. 2004, 126, 5806
57. Neugebauer, R.; Knoche, W. J. Chem. Soc., Perkin Trans. 2 1998, 529
58. Ling, Y.; Wang, W.; Kaifer, A. E. Chem. Commun. 2007, 610
59. Wyman, I. W.; Macartney, D. H. Org. Biomol. Chem. 2008, 6, 1796
60. Liu, L.; Zhao, N.; Scherman, O. A. Chem. Commun. 2008, 1070
61. Yu, J.-S.; Wu, F.-G.; Tao, L.-F.; Luo, J.-J.; Yu, Z.-W. Phys. Chem. Chem. Phys. 2011, 13, 3628
62. Pace, T. C. S.; Bohne, C. Adv. Phys. Org. Chem. 2008, 42, 167
63. Spivak, D. A.; Campbell, J. Analyst 2001, 126, 793
64. Kalyanasundaram, K. Photochemistry in Microheterogeneous Systems; Academic Press: Orlando, 1987.
65. Hamai, S. Bull. Chem. Soc. Jpn. 1982, 55, 2721
66. Nelson, G.; Patonay, G.; Warner, I. M. Appl. Spectrosc. 1987, 41, 1235
67. Barros, T. C.; Stefaniak, K.; Holzwarth, J. F.; Bohne, C. J. Phys. Chem. A 1998, 102, 5639
68. Grabner, G.; Rechthalter, K.; Mayer, B.; Köhler, G. J. Phys. Chem. A 2000, 104, 1365
69. Saleh, N.; Koner, A. L.; Nau, W. M. Angew. Chem., Int. Ed. 2008, 47, 5398
70. Shaikh, M.; Mohanty, J.; Singh, P. K.; Nau, W. M.; Pal, H. Photochem. Photobiol. Sci. 2008, 7, 408
71. Wyman, I. W.; Macartney, D. H. Org. Biomol. Chem. 2010, 8, 247
72. Bohne, C. The Spectrum 2000, 13, 14
73. Buschmann, H. J.; Cleve, E.; Schollmeyer, E. Inorg. Chim. Acta 1992, 193, 93
74. Buschmann, H. J.; Jansen, K.; Meschke, C.; Schollmeyer, E. J. Solution Chem. 1998, 27, 135
75. Jeon, Y.-M.; Kim, J.; Whang, D.; Kim, K. J. Am. Chem. Soc. 1996, 118, 9790
76. Ong, W.; Kaifer, A. E. J. Org. Chem. 2004, 69, 1383
77. Sindelar, V.; Parker, S. E.; Kaifer, A. E. New J. Chem. 2007, 31, 725
78. Rekharsky, M. V.; Ko, Y. H.; Selvapalam, N.; Kim, K.; Inoue, Y. Supramol. Chem. 2007, 19, 39
79. Megyesi, M.; Biczok, L.; Jablonkai, I. J. Phys. Chem. C 2008, 112, 3410
80. Shaikh, M.; Mohanty, J.; Bhasikuttan, A. C.; Uzunova, V. D.; Nau, W. M.; Pal, H. Chem. Commun. 2008, 3681
81. Connors, K. A. Binding Constants-The Measurement of Molecular Complex Stability; John Wiley & Sons: New York, 1987.
82. Mezzina, E.; Cruciani, F.; Pedulli, G. F.; Lucarini, M. Chem.-Eur. J. 2007, 13, 7223
83. Montalti, M.; Credi, A.; Prodi, L.; Gandolfi, M. T. Handbook of Photochemistry; 3rd ed.; CRC Press: Boca Raton, FL, 2006.
84. Green, N. M. Biochem. J. 1963, 89, 585
85. Szejtli, J. Chem. Rev. 1998, 98, 1743
86. Mohanty, J.; Bhasikuttan, A. C.; Nau, W. M.; Pal, H. J. Phys. Chem. B 2006, 110, 5132
87. Christoff, M.; Okano, L. T.; Bohne, C. J. Photochem. Photobiol., A 2000, 134, 169
88. Liao, Y.; Frank, J.; Holzwarth, J. F.; Bohne, C. J. Chem. Soc., Chem. Commun. 1995, 199
89. Nau, W. M.; Zhang, X. J. Am. Chem. Soc. 1999, 121, 8022
90. Cramer, F.; Saenger, W.; Spatz, H. C. J. Am. Chem. Soc. 1967, 89, 14
91. Pace, T. C. S.; Bohne, C. Can. J. Chem. 2011, 89, 395
92. Murphy, R. S.; Bohne, C. Photochem. Photobiol. 2000, 71, 35
93. Okano, L. T.; Barros, T. C.; Chou, D. T. H.; Bennet, A. J.; Bohne, C. J. Phys. Chem. B 2001, 105, 2122
94. Ong, W.; Kaifer, A. E. Organometallics 2003, 22, 4181
95. Bohne, C.; Redmond, R. W.; Scaiano, J. C. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991, p 79.