Ion permeation by a folded multiblock amphiphilic oligomer achieved by hierarchical construction of self-assembled nanopores

Journal of the American Chemical Society

Volumn 134, Issue 48, 2012, Pages 19788-19794

  Muraoka, Takahiro ^a   Shima, Tatsuya ^a   Hamada, Tsutomu ^b   Morita, Masamune ^b   Takagi, Masahiro ^b   Tabata, Kazuhito V ^c   Noji, Hiroyuki ^c   Kinbara, Kazushi ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1-FORMS; ALKALI METAL CATIONS; ALTERNATING SEQUENCES; AMPHIPHILIC MOLECULES; AMPHIPHILICS; BIOLOGICAL MACROMOLECULE; CONDUCTANCE MEASUREMENT; FOLDED CONFORMATION; FOLDED STRUCTURES; HIGHER-ORDER STRUCTURE; HYDROPHILIC AND HYDROPHOBIC; ION PERMEATION; LIPOSOMAL MEMBRANES; MULTI-PASS; MULTIBLOCKS; SELF-ASSEMBLED; STACKED STRUCTURE; TRANS-MEMBRANE PROTEINS;

BIOPHYSICS; HYDROPHOBICITY; POSITIVE IONS; PROTEINS;

OLIGOMERS;

AMPHOPHILE; LIPOSOME; MEMBRANE PROTEIN; OLIGOMER;

ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; FLUORESCENCE ANALYSIS; HYDROPHILICITY; HYDROPHOBICITY; ION CONDUCTANCE; ION TRANSPORT; MEMBRANE VESICLE; MICROSCOPY; NANOPORE; OSMOTIC PRESSURE; PHOSPHOLIPID BILAYER;

HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; IONS; LIPID BILAYERS; MOLECULAR STRUCTURE; NANOPORES; OLIGODEOXYRIBONUCLEOTIDES; PROTEIN FOLDING; SPECTROMETRY, FLUORESCENCE; UNILAMELLAR LIPOSOMES;

EID: 84870688870     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja308342g     Document Type: Article

References (82)

1. Hille, B. Ion Channels of Excitable Membranes, 3 rd ed.; Sinauer Associates: Sunderland, MA, 2001.
2. Busschaert, N.; Kirby, I. L.; Young, S.; Coles, S. J.; Horton, P. N.; Light, M. E.; Gale, P. A. Angew. Chem., Int. Ed. 2012, 51, 4426-4430
3. Bahmanjah, S.; Zhang, N.; Davis, J. T. Chem. Commun. 2012, 48, 4432-4434
4. Busschaert, N.; Wenzel, M.; Light, M. E.; Iglesias-Hernández, P.; Pérez-Tomás, R.; Gale, P. A. J. Am. Chem. Soc. 2011, 133, 14136-14148
5. Hussain, S.; Brotherhood, P. R.; Judd, L. W.; Davis, A. P. J. Am. Chem. Soc. 2011, 133, 1614-1617
6. De. Cola, C.; Licen, S.; Comegna, D.; Cafaro, E.; Bifulco, G.; Izzo, I.; Tecilla, P.; De Riccardis, F. Org. Biomol. Chem. 2009, 7, 2851-2854
7. Davis, J. T.; Gale, P. A.; Okunola, O. A.; Prados, P.; Iglesias-Sánchez, J. C.; Torroba, T.; Quesada, R. Nature Chem. 2009, 1, 138-144
8. Si, W.; Chen, L.; Hu, X.-B.; Tang, G.; Chen, Z.; Hou, J.-L.; Li, Z.-T. Angew. Chem., Int. Ed. 2011, 50, 12564-12568
9. Weiss, L. A.; Sakai, N.; Ghebremariam, B.; Ni, C.; Matile, S. J. Am. Chem. Soc. 1997, 119, 12142-12149
10. Zhou, X.; Liu, G.; Yamato, K.; Shen, Y.; Cheng, R.; Wei, X.; Bai, W.; Gao, Y.; Li, H.; Liu, Y.; Liu, F.; Czajkowsky, D. M.; Wang, J.; Dabney, M. J.; Cai, Z.; Hu, J.; Bright, F. V.; He, L.; Zeng, X. C.; Shao, Z.; Gong, B. Nat. Commun. 2012, 3, 949
11. Hennig, A.; Fischer, L.; Guichard, G.; Matile, S. J. Am. Chem. Soc. 2009, 131, 16889-16895
12. Cazacu, A.; Legrand, Y.-M.; Pasc, A.; Nasr, G.; van der Lee, A.; Mahon, E.; Barboiu, M. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 8117-8122
13. Biron, E.; Otis, F.; Meillon, J.-C.; Robitaille, M.; Lamothe, J.; van Hove, P.; Cormier, M.-E.; Voyer, N. Bioorg. Med. Chem. 2004, 12, 1279-1290
14. Ghadiri, M. R.; Granja, J. R.; Buehler, L. K. Nature 1994, 369, 301-304
15. Roks, M. F. M.; Nolte, R. J. M. Macromolecules 1992, 25, 5398-5407
16. Tabushi, I.; Kuroda, Y.; Yokota, K. Tetrahedron Lett. 1982, 23, 4601-4604
17. Moszynski, J. M.; Fyles, T. M. Org. Biomol. Chem. 2011, 9, 7468-7475
18. Wilson, C. P.; Boglio, C.; Ma, L.; Cockroft, S. L.; Webb, S. J. Chem.-Eur. J. 2011, 17, 3465-3473
19. Jung, M.; Kim, H.; Baek, K.; Kim, K. Angew. Chem., Int. Ed. 2008, 47, 5755-5757
20. Li, X.; Shen, B.; Yao, X.-Q.; Yang, D. J. Am. Chem. Soc. 2007, 129, 7264-7265
21. Schrey, A.; Vescovi, A.; Knoll, A.; Rickert, C.; Koert, U. Angew. Chem., Int. Ed. 2000, 39, 900-902
22. Murillo, O.; Suzuki, I.; Abel, E.; Murray, C. L.; Meadows, E. S.; Jin, T.; Gokel, G. W. J. Am. Chem. Soc. 1997, 119, 5540-5549
23. Kobuke, Y.; Ueda, K.; Sokabe, M. J. Am. Chem. Soc. 1992, 114, 7618-7622
24. Fuhrhop, J.-H.; Liman, U.; Koesling, V. J. Am. Chem. Soc. 1988, 110, 6840-6845
25. Lear, J. D.; Wasserman, Z. R.; De Grado, W. F. Science 1988, 240, 1177-1181
26. Boudreault, P.-L.; Voyer, N. Org. Biomol. Chem. 2007, 5, 1459-1465
27. Vandenburg, Y. R.; Smith, B. D.; Biron, E.; Voyer, N. Chem. Commun. 2002, 1694-1695
28. Tanaka, H.; Litvinchuk, S.; Tran, D.-H.; Bollot, G.; Mareda, J.; Sakai, N.; Matile, S. J. Am. Chem. Soc. 2006, 128, 16000-16001
29. Cho, H.; Widanapathirana, L.; Zhao, Y. J. Am. Chem. Soc. 2011, 133, 141-147
30. Yang, L.; Gordon, V. D.; Mishra, A.; Som, A.; Purdy, K. R.; Davis, M. A.; Tew, G. N.; Wong, G. C. L. J. Am. Chem. Soc. 2007, 129, 12141-12147
31. Litvinchuk, S.; Bollot, G.; Mareda, J.; Som, A.; Ronan, D.; Shah, M. R.; Perrottet, P.; Sakai, N.; Matile, S. J. Am. Chem. Soc. 2004, 126, 10067-10075
32. Otis, F.; Racine-Berthiaume, C.; Voyer, N. J. Am. Chem. Soc. 2011, 133, 6481-6483
33. Handbook of Cell-Penetrating Peptides; Langel, Ü, Ed.; CRC Press: Boca Raton, FL, 2007.
34. Boudreault, P.-L.; Arseneault, M.; Otis, F.; Voyer, N. Chem. Commun. 2008, 2118-2120
35. Leevy, W. M.; Huettner, J. E.; Pajewski, R.; Schlesinger, P. H.; Gokel, G. W. J. Am. Chem. Soc. 2004, 126, 15747-15753
36. Petsko, G. A.; Ringe, D. Protein Structure and Function; New Science Press: London, 2004.
37. Juwarker, H.; Suk, J.; Jeong, K.-S. Chem. Soc. Rev. 2009, 38, 3316-3325
38. Saraogi, I.; Hamilton, A. D. Chem. Soc. Rev. 2009, 38, 1726-1743
39. Bao, C.; Kauffmann, B.; Gan, Q.; Srinivas, K.; Jiang, H.; Huc, I. Angew. Chem., Int. Ed. 2008, 47, 4153-4156
40. Horne, W. S.; Gellman, S. H. Acc. Chem. Res. 2008, 41, 1399-1408
41. Horne, W. S.; Price, J. L.; Keck, J. L.; Gellman, S. H. J. Am. Chem. Soc. 2007, 129, 4178-4180
42. Daniels, D. S.; Petersson, E. J.; Qiu, J. X.; Schepartz, A. J. Am. Chem. Soc. 2007, 129, 1532-1533
43. Foldamers: Structure, Properties, and Applications; Hecht, S.; Huc, I., Eds.; Wiley-VCH: Weinheim, 2007.
44. Goto, H.; Katagiri, H.; Furusho, Y.; Yashima, E. J. Am. Chem. Soc. 2006, 128, 7176-7178
45. Sinkeldam, R. W.; van Houtem, M. H. C. J.; Pieterse, K.; Vekemans, J. A. J. M.; Meijer, E. W. Chem.-Eur. J. 2006, 12, 6129-6137
46. Jones, T. V.; Slutsky, M. M.; Laos, R.; de Greef, T. F. A.; Tew, G. N. J. Am. Chem. Soc. 2005, 127, 17235-17240
47. Abe, H.; Masuda, N.; Waki, M.; Inouye, M. J. Am. Chem. Soc. 2005, 127, 16189-16196
48. Ghosh, S.; Ramakrishnan, S. Angew. Chem., Int. Ed. 2004, 43, 3264-3268
49. Wang, W.; Li, L.-S.; Helms, G.; Zhou, H.-H.; Li, A. D. Q. J. Am. Chem. Soc. 2001, 125, 1120-1121
50. Nakano, T.; Okamoto, Y. Chem. Rev. 2001, 101, 4013-4038
51. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4011
52. Berl, V.; Huc, I.; Khoury, R. G.; Krische, M. J.; Lehn, J.-M. Nature 2000, 407, 720-723
53. Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180
54. Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793-1796
55. Lokey, R. S.; Iverson, B. L. Nature 1995, 375, 303-305
56. Muraoka, T.; Shima, T.; Hamada, T.; Morita, M.; Takagi, M.; Kinbara, K. Chem. Commun. 2011, 47, 194-196
57. Levitus, M.; Schmieder, K.; Ricks, H.; Shimizu, K. D.; Bunz, U. H. F.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 2001, 123, 4259-4265
58. Hamada, T.; Sugimoto, R.; Vestergaard, M.; Nagasaki, T.; Takagi, M. J. Am. Chem. Soc. 2010, 132, 10528-10532
59. Morita, M.; Vestergaard, M.; Hamada, T.; Takagi, M. Biophys. Chem. 2010, 147, 81-86
60. Ishii, K.; Hamada, T.; Hatakeyama, M.; Sugimoto, R.; Nagasaki, T.; Takagi, M. ChemBioChem 2009, 10, 251-256
61. Hamada, T.; Miura, Y.; Ishii, K.; Araki, S.; Yoshikawa, K.; Vestergaard, M.; Takagi, M. J. Phys. Chem. B 2007, 111, 10853-10857
62. Weiss, L. A.; Sakai, N.; Ghebremariam, B.; Ni, C.; Matile, S. J. Am. Chem. Soc. 1997, 119, 12142-12149
63. Ren, J.; Lew, S.; Wang, Z.; London, E. Biochemistry 1997, 36, 10213-10220
64. Ladokhin, A. S. Methods Enzymol. 1997, 278, 462-473
65. Yanagisawa, M.; Imai, M.; Taniguchi, T. Phys. Rev. Lett. 2008, 100, 148102
66. Hamada, T.; Miura, Y.; Ishii, K.; Araki, S.; Yoshikawa, K.; Vestergaard, M.; Takagi, M. J. Phys. Chem. B 2007, 111, 10853-10857
67. Hotani, H. J. Mol. Biol. 1984, 178, 113-120
68. Rawicz, W.; Olbrich, K. C.; McIntosh, T.; Needham, D.; Evans, E. Biophys. J. 2000, 79, 328-339
69. Evans, E.; Rawicz, W. Phys. Rev. Lett. 1990, 64, 2094-2097
70. Even in the case of molecules such as cholesterol that are favorable for the flip-flop motion, the rate is 10-s order. Lasic, D. D., Liposomes: From Physics to Applications; Elsevier: Amsterdam, 1993.
71. Hessel, E.; Herrmann, A.; Müller, P.; Schnerkamp, P. P. M.; Hofmann, K.-P. Eur. J. Biochem. 2000, 267, 1473-1483
72. One hundred and twenty-six molecules of 1 are evaluated to be involved in the orifice in this condition; see Lewis, B. A.; Excelman, D. M. J. Mol. Biol. 1983, 166, 211-217
73. Clement, N. R.; Gould, J. M. Biochemistry 1981, 20, 1534-1538
74. Kano, K.; Fendler, J. H. Biochim. Biophys. Acta 1978, 509, 289-299
75. Eisenman, G.; Horn, R. J. Membr. Biol. 1983, 76, 197-225
76. Tedesco, M. M.; Ghebremariam, B.; Sakai, N.; Matile, S. Angew. Chem., Int. Ed. 1999, 38, 540-543
77. Kumpf, R. A.; Dougherty, D. A. Science 1993, 261, 1708-1710
78. Hill, A. V. Biochem. J. 1913, 7, 471-480
79. Smart, O. S.; Breed, J.; Smith, G. R.; Sansom, M. S. P. Biophys. J. 1997, 72, 1109-1126
80. Hall, J. E. J. Gen. Physiol. 1975, 66, 531-532
81. Chow, Y. L.; Yovanovich, M. M. J. Appl. Phys. 1982, 53, 8470-8475
82. Tabata, K. V.; Sato, K.; Ide, T.; Nishizaka, T.; Nakano, A.; Noji, H. EMBO J. 2009, 28, 3279-3289