Artificial ion channel formed by cucurbit[n]uril derivatives with a carbonyl group fringed portal reminiscent of the selectivity filter of K + channels

Journal of the American Chemical Society

Volumn 126, Issue 49, 2004, Pages 15944-15945

  Young, Jin Jeon ^a   Kim, Hyejung ^a   Jon, Sangyong ^a,b   Selvapalam, Narayanan ^a   Dong, Hyun Oh ^a   Seo, Inra ^b   Park, Chul Seung ^b   Seung, Ryoung Jung ^a   Koh, Duk Su ^a   Kim, Kimoon ^a  

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

^b Gwangju Institute of Science and Technology (GIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; ION CHANNEL; METAL ION; POTASSIUM CHANNEL;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; FLUOROMETRY; ION CURRENT;

BIOMIMETIC MATERIALS; BRIDGED COMPOUNDS; CATIONS; FLUORESCENCE; IMIDAZOLES; LIPID BILAYERS; MEMBRANE POTENTIALS; METALS; POTASSIUM CHANNELS; SUBSTRATE SPECIFICITY;

EID: 10344238621     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044748j     Document Type: Article

References (41)

1. (a) Gokel, G. W.; Mukhopadhyay, A. Chem. Soc. Rev. 2001, 30, 274.
2. (b) Gokel, G. W.; Murillo, O. Acc. Chem. Res. 1996, 29, 425.
3. (c) Matile, S. Chem. Soc. Rev. 2001, 30, 158.
4. (d) Matile, S.; Som, A.; Sordé, N. Tetrahedron 2004, 60, 6405.
5. (e) Mitchell, K. D. D.; Fyles, T. M. In Encyclopedia of Supramolecular Chemistry; Atwood, J. L., Steed, J. W., Eds.; Marcel Dekker: New York, 2004; p 742.
6. Hille, B. Ionic Channels of Excitable Membranes, 2nd ed.; Sinauer Associates: Sunderland, MA, 1992.
7. (a) Fernandez-Lopez, S.; Kim, H.-S.; Choi, E. C.; Delgado, M.; Granja, J. R.; Khasanov, A.; Kraehenbuehl, K.; Long, G.; Weinberger, D. A.; Wilkoxen, K. M.; Ghadiri, M. R. Nature 2001, 412, 452.
8. (b) Sidorov, V.; Kotch, F. W.; Kueber, J. L.; Lam, Y.-F.; Davis, J. T. J. Am. Chem. Soc. 2003, 125, 2840.
9. (a) Gu, L.-Q.; Braha, O.; Conlan, S.; Cheley, S.; Bayley, H. Nature 1999, 398, 686.
10. (b) Cornell, B. A.; Braach-Maksvytis, V. L. B.; King, L. G.; Osman, P. D. J.; Raguse, B.; Wieczorek, L.; Pace, R. J. Nature 1997, 387, 580.
11. (a) Doyle, D. A.; Cabral, J. M.; Pfuetzner, R. A.; Kuo, A.; Gulbis, J. M.; Cohen, S. L.; Chait, T. C.; MacKinnon, R. Science 1998, 280, 69.
12. (b) Zhou, Y.; Morais-Cabral J. H.; Kaufman, A.; MacKinnon, R. Nature 2001, 414, 43.
13. (a) Pregel, M. J.; Jullien, L.; Canceille, J.; Lacombe, L.; Lehn, J.-M. J. Chem. Soc., Perkin Trans. 2 1995, 417.
14. (b) Murillo, O.; Watanabe, S.; Nakano, A.; Gokel, G. W. J. Am. Chem. Soc. 1995, 117, 7665.
15. (c) Yoshino, N.; Satake, A.; Kokube, Y. Angew. Chem., Int. Ed. 2001, 40, 457.
16. (d) Sidorov, V.; Kotch, F. W.; Abdrakhmanova, G.; Mizani, R.; Fettinger, J. C.; Davis, J. T. J. Am. Chem. Soc. 2002, 124, 2267.
17. (e) Ghadiri, M. R.; Granja, J. R.; Buehler, L. K. Nature 1994, 369, 301.
18. (f) Sakai, N.; Brennan, K. C.; Weiss, L. A.; Matile, S. J. Am. Chem. Soc. 1997, 119, 8726.
19. (g) Merritt, M.; Lanier, M.; Deng, G.; Regen, S. L. J. Am. Chem. Soc. 1998, 120, 8494.
20. (h) Fyles, T. M.; James, T. D.; Kaye, K. C. J. Am. Chem. Soc. 1993, 115, 12315.
21. (i) Kokube, Y.; Ueda, K.; Sokabe, M. J. Am. Chem. Soc. 1992, 114, 7618.
22. (j) Litvinchuk, S.; Bollot, G.; Mareda, J.; Abhigyan, S.; Ronan, D.; Shah, M. R.; Perrottet, P.; Sakai, N.; Matile, S. J. Am. Chem. Soc. 2004, 126, 10067.
23. (a) Mock, W. L. In Comprehensive Supramolecular Chemistry; Vögtle, F., Ed.; Pergamon: Oxford, 1996; Vol. 2, p 447.
24. (b) Kim, K.; Kim, H.-J. In Encyclopedia of Supramolecular Chemistry; Atwood, J. L., Steed, J. W., Eds.; Marcel Dekker: New York, 2004; p 390.
25. A recent review: Kim, K. Chem. Soc. Rev. 2002, 31, 96.
26. (a) 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.
27. (b) Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Acc. Chem. Res. 2003, 36, 621.
28. Jon, S. Y.; Selvapalam, N.; Oh, D. H.; Kans, J.-K.; Kim, S.-Y.; Jeon, Y. J.; Lee, J. W.; Kim, K. J. Am. Chem. Soc. 2003, 125, 10186.
29. Zhao J.; Kim, H.-J.; Oh, J.; Kim, S.-Y.; Lee, J. W.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 2001, 40, 4233.
30. Kano, K.; Pendler, J. H. Biochim. Biophys. Acta 1978, 509, 289.
31. Zhang, X. X.; Krakowiak, K. E.; Xue, G.; Bradshaw, J. S.; Izatt, R. M. Ind. Eng. Chem. Res. 2000, 39, 3516.
32. (a) Miller, C. Ion Channel Reconstitution; Plenum Press: New York, 1986.
33. (b) Ashley, R. H. Ion Channels: A Practical Approach; IRL Press: Oxford, 1995.
34. (c) Montal, M.; Mueller, P. Proc. Natl. Acd. Sci. U.S.A. 1972, 69, 3561.
35. 9b See Supporting Information.
36. -3 for NaCl. Rate constants for the KCl, RbCl, CsCl are no more than the background.
37. The sequence lies on the borderline of Eisenman sequence I and II with "Li anomaly". Considering diameter of CB[6] portal, transport sequence is well-justified. See: (a) Eisenman, G.; Horn, R. J. Membr. Biol. 1983, 76, 197. (b) Laio, T.; Torre, V. Biophys. J. 1999, 76, 129. (c) Tedesco, M. M.; Ghebremariam, B.; Sakai, N.; Matile, S. Angew. Chem., Int. Ed. 1999, 38, 540.
38. The sequence lies on the borderline of Eisenman sequence I and II with "Li anomaly". Considering diameter of CB[6] portal, transport sequence is well-justified. See: (a) Eisenman, G.; Horn, R. J. Membr. Biol. 1983, 76, 197. (b) Laio, T.; Torre, V. Biophys. J. 1999, 76, 129. (c) Tedesco, M. M.; Ghebremariam, B.; Sakai, N.; Matile, S. Angew. Chem., Int. Ed. 1999, 38, 540.
39. The sequence lies on the borderline of Eisenman sequence I and II with "Li anomaly". Considering diameter of CB[6] portal, transport sequence is well-justified. See: (a) Eisenman, G.; Horn, R. J. Membr. Biol. 1983, 76, 197. (b) Laio, T.; Torre, V. Biophys. J. 1999, 76, 129. (c) Tedesco, M. M.; Ghebremariam, B.; Sakai, N.; Matile, S. Angew. Chem., Int. Ed. 1999, 38, 540.
40. Williams, K. Biochem. J. 1997, 325, 289.
41. 7 ions/s. Rostovtseva, T. K.; Aguilella, V. M.; Vodyanoy, I.; Bezrukov, S. M.; Parsegian, V. A. Biophys. J. 1998, 75, 1783.