Bilayer clamp experiment
8 O. Murillo, S. Watanabe, A. Nakano and G. W. Gokel, J. Am.
Chem. Soc., 1995, 117, 7665–7679.
The general experimental procedure used a previously de-
scribed system and followed previous protocols.21,44 Mem-
branes were formed from diphtanoyl phosphatidyl choline
(Avnti Polar Lipids; 5 mg in 200 ml of decane) by brushing
and/or dipping as previously described. Active channels were
formed by brushing a solution of 13 and 3 (10 mM in Pd) in
ACN across a pre-formed bilayer membrane. Membrane
activity and the analysis of short and long openings was
described in the text using published solution resistivity data.43
The following short openings were observed for 13 : 3
mixtures (1 : 1 mole ratio; electrolyte, conductance in nS,
Hille radius in nm): 1 M KNO3, 0.123, 1.0; 1 M KCl, 0.009,
0.10; 1 M KCl, 0.010, 0.10; 1 M KNO3, 0.148, 0.11; 1 M
KNO3, 0.150, 0.11; 1 M KNO3, 0.197, 0.13; 1 M KNO3, 0.212,
0.13; 1 M KCl, 0.016, 0.13; 1 M KCl, 0.016, 0.13; 0.1 M NaCl,
0.017, 1.3; 1 M KNO3, 0.248, 1.4; 1 M KNO3, 0.265, 1.5; 1 M
KNO3, 0.318, 0.16; 1 M KNO3, 0.381, 0.18; 1 M KCl, 0.040,
0.21; 0.1 M NaCl, 0.046, 0.23; 1 M KNO3, 0.638, 0.23; 1 M
KNO3, 0.750, 0.25; 1 M KNO3, 0.813, 0.26; 0.1 M NaCl,
0.087, 0.32; 0.1 M NaCl, 0.349, 0.68.
9 C. L. Murray, E. S. Meadows, O. Murillo and G. W. Gokel, J. Am.
Chem. Soc., 1997, 119, 7887–7888.
10 W. M. Leevy, M. E. Weber, P. H. Schlesinger and G. W. Gokel,
Chem. Commun., 2005, 89–91.
11 W. M. Leevy, J. E. Huettner, R. Pajewski, P. H. Schlesinger and G.
W. Gokel, J. Am. Chem. Soc., 2004, 126, 15747–15753.
12 N. Voyer and M. Robitaille, J. Am. Chem. Soc., 1995, 117,
6599–6600.
13 M. F. M. Roks and R. J. M. Nolte, Macromolecules, 1992, 25,
5398–5407.
14 L. Julien and J.-M. Lehn, J. Inclusion Phenom. Mol. Recognit.
Chem., 1992, 12, 55–74.
15 V. E. Carmichael, P. J. Dutton, T. M. Fyles, T. D. James, J. A.
Swan and M. Zojaji, J. Am. Chem. Soc., 1989, 111, 767–769.
16 S. Matile, A. Som and N. Sorde, Tetrahedron, 2004, 60, 6405–6435.
17 N. Sakai, J. Mareda and S. Matile, Acc. Chem. Res., 2005, 38,
79–87.
18 T. D. Clark, L. K. Buehler and M. R. Ghadiri, J. Am. Chem. Soc.,
1998, 120, 651–656.
19 M. R. Ghadiri, J. R. Granja and L. K. Buehler, Nature, 1994, 369,
301–304.
20 T. D. Clark, J. M. Buriak, Kobayashi, M. P. Isler, D. E. McRee
and M. R. Ghadiri, J. Am. Chem. Soc., 1998, 120, 8949–8962.
21 P. K. Eggers, T. M. Fyles, K. D. D. Mitchell and T. Sutherland, J.
Org. Chem., 2003, 68, 1050–1058.
22 L. M. Cameron, T. M. Fyles and C. Hu, J. Org. Chem., 2002, 67,
1548–1553.
The following long openings were observed for 13 : 3
mixtures (1 : 4 mole ratio; electrolyte, conductance in nS,
Hille radius in nm): 0.5 M Cs2SO4, 0.12, 0.13; 0.1 M CsBr,
0.066, 0.25; 0.1 M CsCl, 0.29, 0.51; 0.1 M Cs2SO4, 0.8, 0.73;
0.1 M NaCl, 0.52, 0.81; 0.1 M Cs2SO4, 1.3, 0.96; 1 M KNO3,
7.21, 1.25; 0.1 M Cs2SO4, 2.1, 1.30; 0.1 M CsCl, 1.7, 1.45.
The following long openings were observed for 13 alone
(electrolyte, conductance in nS, Hille radius in nm): 1 M
KNO3, 0.251, 0.19; 1 M KNO3, 0.26, 0.19.
23 T. M. Fyles, R. Knoy, K. Mullen and M. Sieffert, Langmuir, 2001,
17, 6669–6674.
¨
24 T. M. Fyles, D. Loock and X. Zhou, J. Am. Chem. Soc., 1998, 120,
2997–3003.
25 T. M. Fyles, D. Heberle, W. F. van Straaten-Nijenhuis and X.
Zhou, Supramol. Chem., 1995, 11, 1–7.
26 T. M. Fyles and C. Hu, J. Supramol. Chem., 2001, 1, 207–215.
27 M. Fujita, M. Tominaga, A. Hori and B. Therrien, Acc. Chem.
Res., 2005, 38, 369–378.
28 M. Fujita, J. Yazaki and K. Ogura, J. Am. Chem. Soc., 1990, 12,
5645–5647.
29 M. Fujita, O. Sasaki, T. Mitsuhashi, T. Fujita, J. Yazaki, K.
Yamaguchi and K. Ogura, Chem. Commun., 1996, 1535–1536.
30 T. M. Fyles and C. Tong, 2006, submitted; C. Tong, PhD thesis,
University of Victoria, 2006.
31 R. H. Ashley, Ion Channels: A Practical Approach, Oxford Uni-
versity Press, Oxford, 1995.
32 B. Hille, Ionic Channels of Excitable Membranes, Sinauer Associ-
ates Incorporated, Sunderland, 2nd edn, 1992.
33 B. Baumeister, N. Sakai and S. Matile, Angew. Chem., Int. Ed.,
2000, 39, 1955–1958.
34 J. M. Tercero-Moreno, A. Matila-Hernadez, S. Gonzalez-Garcia
and J. Niclos-Gutierrez, Inorg. Chim. Acta, 1996, 253, 23–29.
35 K. J. Barnham, C. J. Bauer, M. I. Djuran, M. A. Mazid, T. Rau
and P. J. Sadler, Inorg. Chem., 1995, 34, 2826–2832.
36 N. Kimizuka, S. H. Lee and T. Kunitake, Angew. Chem., Int. Ed.,
2000, 39, 389–391.
Acknowledgements
We thank Philippa Carrie for her assistance in the early stages
of the synthesis of 13. This project was supported by the
Natural Sciences and Engineering Research Council of
Canada and the University of Victoria.
It is a pleasure to acknowledge George Gokel as a pioneer in
the synthetic channels area. His insights, critiques, collegial
advice, and steady competitive pressure have had an enduring
positive influence on the older author for over twenty-five
years.
37 L. Siskind, A. Davoody, S. Marshall and M. Colombini, Biophys.
J., 2003, 85, 1560–1575.
References
1 G. W. Gokel and A. Mukhopadhyay, Chem. Soc. Rev., 2001, 30,
274–286.
38 L. Siskind and M. Colombini, J. Biol. Chem., 2000, 275,
38640–38644.
2 M. J. Pregel, L. Jullien, J. Canceill, L. Lacombe and J.-M. Lehn, J.
Chem. Soc., Perkin Trans. 2, 1995, 417–426.
39 J. Israelachvili, Intermolecular and Surface Forces, Academic Press,
London, 2nd edn, 1992.
3 I. Tabushi, Y. Kuroda and K. Yokota, Tetrahedron Lett., 1982, 23,
4601–4604.
40 D. Allende, S. A. Simon and T. J. McIntosh, Biophys. J., 2005, 88,
1828–1837.
4 G. W. Gokel, R. Ferdani, J. Liu, R. Pajewski, H. Shabany and P.
Uetrecht, Chem.–Eur. J., 2001, 7, 33–39.
41 K. Matsuzaki, O. Murase, N. Fujii and K. Miyajima, Biochem-
istry, 1996, 35, 11361–11368.
5 G. W. Gokel, Chem. Commun., 2000, 1–9.
6 G. E. M. Maguire, E. S. Meadows, C. L. Murray and G. W.
Gokel, Tetrahedron Lett., 1997, 38, 6339–6342.
7 O. Murillo, I. Suzuki, E. Abel and G. W. Gokel, J. Am. Chem.
Soc., 1996, 118, 7628–7629.
42 H. Bayley and P. S. Cremer, Nature, 2001, 413, 226–230.
43 R. J. S. Lewis, Sax’s dangerous properties of industrial materials,
Wiley-Interscience, Hoboken, NJ, USA, 2004.
44 M. B. Buchmann, T. M. Fyles and T. Sutherland, Bioorg. Med.
Chem., 2004, 12, 1315–1324.
ꢀc
This journal is the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2007
New J. Chem., 2007, 31, 655–661 | 661