A synthetic cation-transporting calix[4]arene derivative active in phospholipid bilayers

Angewandte Chemie - International Edition

Volumn 37, Issue 11, 1998, Pages 1534-1537

  De Mendoza, Javier ^a   Cuevas, Félix ^a   Prados, Pilar ^a   Meadows, Eric S ^b   Gokel, George W ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Calixarenes; Ion channels; Membranes

Indexed keywords

EID: 0032546777     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980619)37:11<1534::AID-ANIE1534>3.0.CO;2-B     Document Type: Article

References (42)

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12. Some leading references: a) I. Tabushi, Y. Kuroda, K. Yokota, Tetrahedron Lett. 1982, 23, 4601-4604; b) M. F. M. Roks, R. J. M. Nolte, Macromolecules 1992, 25, 5398-5403; c) M. Pregel, L. Jullien, J. Canceill, L. Lacombe, J.-M. Lehn, J. Chem. Soc. Perkin Trans. 2 1995, 417-426; d) V. E. Carmichael, P. Dutton, T. Fyles, T. James, J. Swan, M. Zojaji, J. Am. Chem. Soc. 1989, 111, 767-769; e) K. Kaye, T. Fyles, ibid. 1993, 115, 12315-12321; f) M. R. Ghadiri, J. R. Granja, L. K. Buehler, Nature 1994, 369, 301-304; g) N. Voyer, M. Robitaille, J. Am. Chem. Soc. 1995, 117, 6599-6600; h) Y. Tanaka, Y. Kobuke, M. Sokabe, Angew. Chem. 1995, 107, 717-719; Angew. Chem. Int. Ed. Engl. 1995, 34, 693-694; i) G. Deng, M. Merritt, K. Yamashita, V. Janout, A. Sadownik, S. L. Regen, J. Am. Chem. Soc. 1996, 118, 3307-3308; j) H. Wagner, K. Harms, U. Koert, S. Meder, G. Boheim, Angew. Chem. 1996, 108, 2836-2839; Angew. Chem. Int. Ed. Engl. 1996, 35, 2643-2646; k) S. Das, U. D. Lengweiler, D. Seebach, R. N. Reusch, Proc. Natl. Acad. Sci. USA 1997, 94, 9075-9079, and references therein.
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14. Some leading references: a) I. Tabushi, Y. Kuroda, K. Yokota, Tetrahedron Lett. 1982, 23, 4601-4604; b) M. F. M. Roks, R. J. M. Nolte, Macromolecules 1992, 25, 5398-5403; c) M. Pregel, L. Jullien, J. Canceill, L. Lacombe, J.-M. Lehn, J. Chem. Soc. Perkin Trans. 2 1995, 417-426; d) V. E. Carmichael, P. Dutton, T. Fyles, T. James, J. Swan, M. Zojaji, J. Am. Chem. Soc. 1989, 111, 767-769; e) K. Kaye, T. Fyles, ibid. 1993, 115, 12315-12321; f) M. R. Ghadiri, J. R. Granja, L. K. Buehler, Nature 1994, 369, 301-304; g) N. Voyer, M. Robitaille, J. Am. Chem. Soc. 1995, 117, 6599-6600; h) Y. Tanaka, Y. Kobuke, M. Sokabe, Angew. Chem. 1995, 107, 717-719; Angew. Chem. Int. Ed. Engl. 1995, 34, 693-694; i) G. Deng, M. Merritt, K. Yamashita, V. Janout, A. Sadownik, S. L. Regen, J. Am. Chem. Soc. 1996, 118, 3307-3308; j) H. Wagner, K. Harms, U. Koert, S. Meder, G. Boheim, Angew. Chem. 1996, 108, 2836-2839; Angew. Chem. Int. Ed. Engl. 1996, 35, 2643-2646; k) S. Das, U. D. Lengweiler, D. Seebach, R. N. Reusch, Proc. Natl. Acad. Sci. USA 1997, 94, 9075-9079, and references therein.
15. Some leading references: a) I. Tabushi, Y. Kuroda, K. Yokota, Tetrahedron Lett. 1982, 23, 4601-4604; b) M. F. M. Roks, R. J. M. Nolte, Macromolecules 1992, 25, 5398-5403; c) M. Pregel, L. Jullien, J. Canceill, L. Lacombe, J.-M. Lehn, J. Chem. Soc. Perkin Trans. 2 1995, 417-426; d) V. E. Carmichael, P. Dutton, T. Fyles, T. James, J. Swan, M. Zojaji, J. Am. Chem. Soc. 1989, 111, 767-769; e) K. Kaye, T. Fyles, ibid. 1993, 115, 12315-12321; f) M. R. Ghadiri, J. R. Granja, L. K. Buehler, Nature 1994, 369, 301-304; g) N. Voyer, M. Robitaille, J. Am. Chem. Soc. 1995, 117, 6599-6600; h) Y. Tanaka, Y. Kobuke, M. Sokabe, Angew. Chem. 1995, 107, 717-719; Angew. Chem. Int. Ed. Engl. 1995, 34, 693-694; i) G. Deng, M. Merritt, K. Yamashita, V. Janout, A. Sadownik, S. L. Regen, J. Am. Chem. Soc. 1996, 118, 3307-3308; j) H. Wagner, K. Harms, U. Koert, S. Meder, G. Boheim, Angew. Chem. 1996, 108, 2836-2839; Angew. Chem. Int. Ed. Engl. 1996, 35, 2643-2646; k) S. Das, U. D. Lengweiler, D. Seebach, R. N. Reusch, Proc. Natl. Acad. Sci. USA 1997, 94, 9075-9079, and references therein.
16. Some leading references: a) I. Tabushi, Y. Kuroda, K. Yokota, Tetrahedron Lett. 1982, 23, 4601-4604; b) M. F. M. Roks, R. J. M. Nolte, Macromolecules 1992, 25, 5398-5403; c) M. Pregel, L. Jullien, J. Canceill, L. Lacombe, J.-M. Lehn, J. Chem. Soc. Perkin Trans. 2 1995, 417-426; d) V. E. Carmichael, P. Dutton, T. Fyles, T. James, J. Swan, M. Zojaji, J. Am. Chem. Soc. 1989, 111, 767-769; e) K. Kaye, T. Fyles, ibid. 1993, 115, 12315-12321; f) M. R. Ghadiri, J. R. Granja, L. K. Buehler, Nature 1994, 369, 301-304; g) N. Voyer, M. Robitaille, J. Am. Chem. Soc. 1995, 117, 6599-6600; h) Y. Tanaka, Y. Kobuke, M. Sokabe, Angew. Chem. 1995, 107, 717-719; Angew. Chem. Int. Ed. Engl. 1995, 34, 693-694; i) G. Deng, M. Merritt, K. Yamashita, V. Janout, A. Sadownik, S. L. Regen, J. Am. Chem. Soc. 1996, 118, 3307-3308; j) H. Wagner, K. Harms, U. Koert, S. Meder, G. Boheim, Angew. Chem. 1996, 108, 2836-2839; Angew. Chem. Int. Ed. Engl. 1996, 35, 2643-2646; k) S. Das, U. D. Lengweiler, D. Seebach, R. N. Reusch, Proc. Natl. Acad. Sci. USA 1997, 94, 9075-9079, and references therein.
17. Some leading references: a) I. Tabushi, Y. Kuroda, K. Yokota, Tetrahedron Lett. 1982, 23, 4601-4604; b) M. F. M. Roks, R. J. M. Nolte, Macromolecules 1992, 25, 5398-5403; c) M. Pregel, L. Jullien, J. Canceill, L. Lacombe, J.-M. Lehn, J. Chem. Soc. Perkin Trans. 2 1995, 417-426; d) V. E. Carmichael, P. Dutton, T. Fyles, T. James, J. Swan, M. Zojaji, J. Am. Chem. Soc. 1989, 111, 767-769; e) K. Kaye, T. Fyles, ibid. 1993, 115, 12315-12321; f) M. R. Ghadiri, J. R. Granja, L. K. Buehler, Nature 1994, 369, 301-304; g) N. Voyer, M. Robitaille, J. Am. Chem. Soc. 1995, 117, 6599-6600; h) Y. Tanaka, Y. Kobuke, M. Sokabe, Angew. Chem. 1995, 107, 717-719; Angew. Chem. Int. Ed. Engl. 1995, 34, 693-694; i) G. Deng, M. Merritt, K. Yamashita, V. Janout, A. Sadownik, S. L. Regen, J. Am. Chem. Soc. 1996, 118, 3307-3308; j) H. Wagner, K. Harms, U. Koert, S. Meder, G. Boheim, Angew. Chem. 1996, 108, 2836-2839; Angew. Chem. Int. Ed. Engl. 1996, 35, 2643-2646; k) S. Das, U. D. Lengweiler, D. Seebach, R. N. Reusch, Proc. Natl. Acad. Sci. USA 1997, 94, 9075-9079, and references therein.
18. Some leading references: a) I. Tabushi, Y. Kuroda, K. Yokota, Tetrahedron Lett. 1982, 23, 4601-4604; b) M. F. M. Roks, R. J. M. Nolte, Macromolecules 1992, 25, 5398-5403; c) M. Pregel, L. Jullien, J. Canceill, L. Lacombe, J.-M. Lehn, J. Chem. Soc. Perkin Trans. 2 1995, 417-426; d) V. E. Carmichael, P. Dutton, T. Fyles, T. James, J. Swan, M. Zojaji, J. Am. Chem. Soc. 1989, 111, 767-769; e) K. Kaye, T. Fyles, ibid. 1993, 115, 12315-12321; f) M. R. Ghadiri, J. R. Granja, L. K. Buehler, Nature 1994, 369, 301-304; g) N. Voyer, M. Robitaille, J. Am. Chem. Soc. 1995, 117, 6599-6600; h) Y. Tanaka, Y. Kobuke, M. Sokabe, Angew. Chem. 1995, 107, 717-719; Angew. Chem. Int. Ed. Engl. 1995, 34, 693-694; i) G. Deng, M. Merritt, K. Yamashita, V. Janout, A. Sadownik, S. L. Regen, J. Am. Chem. Soc. 1996, 118, 3307-3308; j) H. Wagner, K. Harms, U. Koert, S. Meder, G. Boheim, Angew. Chem. 1996, 108, 2836-2839; Angew. Chem. Int. Ed. Engl. 1996, 35, 2643-2646; k) S. Das, U. D. Lengweiler, D. Seebach, R. N. Reusch, Proc. Natl. Acad. Sci. USA 1997, 94, 9075-9079, and references therein.
19. Some leading references: a) I. Tabushi, Y. Kuroda, K. Yokota, Tetrahedron Lett. 1982, 23, 4601-4604; b) M. F. M. Roks, R. J. M. Nolte, Macromolecules 1992, 25, 5398-5403; c) M. Pregel, L. Jullien, J. Canceill, L. Lacombe, J.-M. Lehn, J. Chem. Soc. Perkin Trans. 2 1995, 417-426; d) V. E. Carmichael, P. Dutton, T. Fyles, T. James, J. Swan, M. Zojaji, J. Am. Chem. Soc. 1989, 111, 767-769; e) K. Kaye, T. Fyles, ibid. 1993, 115, 12315-12321; f) M. R. Ghadiri, J. R. Granja, L. K. Buehler, Nature 1994, 369, 301-304; g) N. Voyer, M. Robitaille, J. Am. Chem. Soc. 1995, 117, 6599-6600; h) Y. Tanaka, Y. Kobuke, M. Sokabe, Angew. Chem. 1995, 107, 717-719; Angew. Chem. Int. Ed. Engl. 1995, 34, 693-694; i) G. Deng, M. Merritt, K. Yamashita, V. Janout, A. Sadownik, S. L. Regen, J. Am. Chem. Soc. 1996, 118, 3307-3308; j) H. Wagner, K. Harms, U. Koert, S. Meder, G. Boheim, Angew. Chem. 1996, 108, 2836-2839; Angew. Chem. Int. Ed. Engl. 1996, 35, 2643-2646; k) S. Das, U. D. Lengweiler, D. Seebach, R. N. Reusch, Proc. Natl. Acad. Sci. USA 1997, 94, 9075-9079, and references therein.
20. Some leading references: a) I. Tabushi, Y. Kuroda, K. Yokota, Tetrahedron Lett. 1982, 23, 4601-4604; b) M. F. M. Roks, R. J. M. Nolte, Macromolecules 1992, 25, 5398-5403; c) M. Pregel, L. Jullien, J. Canceill, L. Lacombe, J.-M. Lehn, J. Chem. Soc. Perkin Trans. 2 1995, 417-426; d) V. E. Carmichael, P. Dutton, T. Fyles, T. James, J. Swan, M. Zojaji, J. Am. Chem. Soc. 1989, 111, 767-769; e) K. Kaye, T. Fyles, ibid. 1993, 115, 12315-12321; f) M. R. Ghadiri, J. R. Granja, L. K. Buehler, Nature 1994, 369, 301-304; g) N. Voyer, M. Robitaille, J. Am. Chem. Soc. 1995, 117, 6599-6600; h) Y. Tanaka, Y. Kobuke, M. Sokabe, Angew. Chem. 1995, 107, 717-719; Angew. Chem. Int. Ed. Engl. 1995, 34, 693-694; i) G. Deng, M. Merritt, K. Yamashita, V. Janout, A. Sadownik, S. L. Regen, J. Am. Chem. Soc. 1996, 118, 3307-3308; j) H. Wagner, K. Harms, U. Koert, S. Meder, G. Boheim, Angew. Chem. 1996, 108, 2836-2839; Angew. Chem. Int. Ed. Engl. 1996, 35, 2643-2646; k) S. Das, U. D. Lengweiler, D. Seebach, R. N. Reusch, Proc. Natl. Acad. Sci. USA 1997, 94, 9075-9079, and references therein.
21. Some leading references: a) I. Tabushi, Y. Kuroda, K. Yokota, Tetrahedron Lett. 1982, 23, 4601-4604; b) M. F. M. Roks, R. J. M. Nolte, Macromolecules 1992, 25, 5398-5403; c) M. Pregel, L. Jullien, J. Canceill, L. Lacombe, J.-M. Lehn, J. Chem. Soc. Perkin Trans. 2 1995, 417-426; d) V. E. Carmichael, P. Dutton, T. Fyles, T. James, J. Swan, M. Zojaji, J. Am. Chem. Soc. 1989, 111, 767-769; e) K. Kaye, T. Fyles, ibid. 1993, 115, 12315-12321; f) M. R. Ghadiri, J. R. Granja, L. K. Buehler, Nature 1994, 369, 301-304; g) N. Voyer, M. Robitaille, J. Am. Chem. Soc. 1995, 117, 6599-6600; h) Y. Tanaka, Y. Kobuke, M. Sokabe, Angew. Chem. 1995, 107, 717-719; Angew. Chem. Int. Ed. Engl. 1995, 34, 693-694; i) G. Deng, M. Merritt, K. Yamashita, V. Janout, A. Sadownik, S. L. Regen, J. Am. Chem. Soc. 1996, 118, 3307-3308; j) H. Wagner, K. Harms, U. Koert, S. Meder, G. Boheim, Angew. Chem. 1996, 108, 2836-2839; Angew. Chem. Int. Ed. Engl. 1996, 35, 2643-2646; k) S. Das, U. D. Lengweiler, D. Seebach, R. N. Reusch, Proc. Natl. Acad. Sci. USA 1997, 94, 9075-9079, and references therein.
22. Some leading references: a) I. Tabushi, Y. Kuroda, K. Yokota, Tetrahedron Lett. 1982, 23, 4601-4604; b) M. F. M. Roks, R. J. M. Nolte, Macromolecules 1992, 25, 5398-5403; c) M. Pregel, L. Jullien, J. Canceill, L. Lacombe, J.-M. Lehn, J. Chem. Soc. Perkin Trans. 2 1995, 417-426; d) V. E. Carmichael, P. Dutton, T. Fyles, T. James, J. Swan, M. Zojaji, J. Am. Chem. Soc. 1989, 111, 767-769; e) K. Kaye, T. Fyles, ibid. 1993, 115, 12315-12321; f) M. R. Ghadiri, J. R. Granja, L. K. Buehler, Nature 1994, 369, 301-304; g) N. Voyer, M. Robitaille, J. Am. Chem. Soc. 1995, 117, 6599-6600; h) Y. Tanaka, Y. Kobuke, M. Sokabe, Angew. Chem. 1995, 107, 717-719; Angew. Chem. Int. Ed. Engl. 1995, 34, 693-694; i) G. Deng, M. Merritt, K. Yamashita, V. Janout, A. Sadownik, S. L. Regen, J. Am. Chem. Soc. 1996, 118, 3307-3308; j) H. Wagner, K. Harms, U. Koert, S. Meder, G. Boheim, Angew. Chem. 1996, 108, 2836-2839; Angew. Chem. Int. Ed. Engl. 1996, 35, 2643-2646; k) S. Das, U. D. Lengweiler, D. Seebach, R. N. Reusch, Proc. Natl. Acad. Sci. USA 1997, 94, 9075-9079, and references therein.
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30. [6c] The arrangement of the side chains in these compounds and the lack of planar bilayer conductance make it impossible to compare them directly.
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35. Membranes were formed by coating with L-α-lecithin in decane. All membranes used for the present study had a capacitance of about 100 pF. The channel compounds 1 or 2 were incorporated into the bilayers by stirring the cis chamber for 10 min after addition of the channel as a solution in THF. The electrolyte solutions consisted of NaCl or KCl (0.5 M) and were buffered with phosphate or piperazine-N,N′-bis(2-ethanesulfonic acid) (PIPES) to pH 6.7-7.0 for various trials. After an equilibration period of 5 min a holding voltage was applied, and the channel responses were recorded with a Warner PC-505 patch clamp amplifier, a DigiData A/D converter, and the aquisition software Axoscope.
36. -1) in decane (25°C), and membranes formed over the pinhole.
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