Sodium cation transport in synthetic channels obeys the Hammett relationship in a phospholipid bilayer membrane

Journal of the American Chemical Society

Volumn 118, Issue 32, 1996, Pages 7628-7629

  Murillo, Oscar ^a   Suzuki, Iwao ^a   Abel, Ernesto ^a   Gokel, George W ^a  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROWN ETHER DERIVATIVE; GRAMICIDIN; MACROCYCLIC COMPOUND; VALINOMYCIN;

ARTICLE; BILAYER MEMBRANE; MODEL; PHOSPHOLIPID BILAYER; SODIUM TRANSPORT;

EID: 0029738938     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960950d     Document Type: Article

References (50)

1. Nicholls, D. G. Proteins. Transmitters, and Synapses; Blackwell Science: Oxford, 1994.
2. (a) Henderson, R.; Baldwin, J. M.; Ceska, T. A.; Zemlin, F.; Beckmann, E.; Downing. K. H. J. Mol. Biol. 1990, 213, 899-929.
3. (b) Deisenhofer, J.; Epp, O.; Miki, K.; Huber, R.; Michel, H. Nature 1985, 318, 618-624.
4. (c) Baldwin, J. M. EMBO J. 1993, 12, 1693-1703.
5. (a) Stein, W. D. Channels, Carriers, and Pumps; Academic Press: New York, 1990.
6. (b) Hille, B. Ionic Channels of Excitable Membranes; Sinauer Press: Sunderland, MA, 1992.
7. (a) Mutter, M.; Tuchscherer, G. G.; Miller, C.; Altman, K.-H.; Carey, R. I.; Wyss, D. F.; Labhardt, A. M.; Rivier, J. E. J. Am. Chem. Soc. 1992, 114, 1463.
8. (b) Ckerfeldt, K. S.; Lear, J. D.; Wasserman, Z. R.; Chung, L. A.; DeGrado, W. F. Acc. Chem. Res. 1993, 26, 191-197.
9. (a) Urry, E. W., Goodall, M. C., Glickson, J. D., Meyers, D. F Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1907-1911.
10. (b) Urry, D. W. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 672-676.
11. Bolard, J. Biochim. Biophys. Acta 1986, 864, 257-304.
12. Tabushi, I.; Kuroda, Y.; Yokota, K. Tetrahedron Lett. 1982, 4601-4604.
13. (a) Menger, F. M.; Davis, D. S.; Persichetti, R. A.; Lee, J.-J. J. Am. Chem. Soc. 1990, 112, 2451-2452.
14. (b) Menger, F. M. Bol. Soc. Chil. Quim. 1990, 35 (1), 33-38.
15. (a) Kobuke, Y.; Ueda, K.; Sokabe, M.; J. Am. Chem. Soc. 1992, 114, 7618-1722.
16. (b) Tanaka, Y.; Kobuke, Y.; Sokabe, M. Angew. Chem., Int. Ed. Engl 1995, 4 (6), 693-694.
17. Stadler, E.; Dedek, P.; Yamashita, K.; Regen, S. J. Am. Chem. Soc. 1994, 116, 6677-6682.
18. (a) Carmichael, V. E.; Dutton, P. J.; Fyles, T. M.; James, T. D.; Swan, J. A.; Zojaji, M. J. Am. Chem. Soc. 1989, 111, 767-769
19. (b) Fyles, T. M.; James, T. D.; Kaye, K. C. J. Am. Chem. Soc. 1993, 115, 12315-12321.
20. (c) Fyles, T.; James, T.; Pryhitka, A.; Zojaji, M. J. Org. Chem. 1993, 58, 7456-7468.
21. (d) Fyles, T. M.: Heberle, D.; Van Straaten-Nijenhuis, W. F.; Zhou, X. Supramol. Chem. 1995, 6, 71-78.
22. (a) Jullien, L.; Lehn, J.-M. Tetrahedron Lett. 1988, 3803-3806.
23. (b) Jullien, L.; Lehn, J.-M. J. Inclusion Phenom. 1992, 12, 55-74.
24. (c) Pregel, M. J.; Jullien, L.; Lehn, J.-M.; Angew. Chem., Int. Ed. Engl. 1992, 31, 1637-1640.
25. (d) Canceill, J.; Jullien, L.; Lacombe, L.; Lehn, J.-M. Helv. Chim. Acta 1992, 75, 791.
26. (a) Ghadiri. M. R.; Granja, J. R.; Buehler, L. K. Nature 1994, 369, 301-304.
27. (b) Knazanovich, N.; Granja, J. R.; McRee, D. E.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1994, 116, 6011-6012.
28. Voyer, N.; Robitaille. M. J. Am. Chem. Soc. 1995, 117, 6599-6600.
29. (a) Gokel, G. W.; Hernandez, J. C.; Viscariello, A. M.; Arnold, K. A.; Campana, C. F.; Echegoyen, L.; Fronczek, F. R.; Candour, R. D.; Morgan, C. R.; Trafton, J. E.; Minganti, C.; Eiband, D.; Schultz, R. A.; Tamminen, M. J. Org. Chem. 1987, 52, 2963-2968.
30. (b) Echegoyen, L. E.; Hernandez, J. C.; Kaifer, A.; Gokel, G. W.; Echegoyen. L. J. Chem. Soc., Chem. Commun. 1988, 836-837.
31. (c) Echegoyen, L. E.; Portugal, L.; Miller, S. R.; Hernandez, J. C.; Echegoyen, L.; Gokel, G. W. Tetrahedron Lett. 1988, 29, 4065-4068.
32. (d) Muñoz, S.; Mallén, J. V.; Nakano, A.; Chen, Z.; Echegoyen, L.; Gay, I.; Gokel, G. W. J. Chem. Soc., Chem. Commun. 1992, 520-522.
33. (e) Muñoz, S.; Mallén, J.; Nakano, A.; Chen, Z.; Gay, I.; Echegoyen, L.; Gokel, G. W. J. Am. Chem. Soc. 1993, 115, 1705-1711.
34. Grell, E.; Funek, T.; Eggers, F. In Membranes; Eisenman, G., Ed.; Marcel Dekker: New York, 1975; Vol. 3, p 1.
35. We have developed a shorthand to describe substituted crown compounds: 〈18〉 = 18-crown-6, 〈N15〉 or 〈15N〉 = aza-18-crown-6, and 〈N18N〉 = diaza-18-crown-6. See: Hernandez, J. C.; Trafton, J. E.; Gokel, G. W. Tetrahedron Lett. 1991, 6269-6272
36. Murillo, O.; Watanabe, S.; Nakano, A.; Gokel. G. W. J. Am. Chem. Soc. 1995, 117, 7665.
37. Hendrixson, R. R; Mack, M. P; Palmer, R. A.; Ottolenghi, A.; Ghirardelli, R. G. Toxicol. Appl. Pharmacol., 1978, 44, 263-268.
38. Stolwijk, T. B.; Sudholter, E. J. R.; Reinhoudt, D. N. J. Am. Chem. Soc. 1989, 111, 6321.
39. (-nr) where m = 5 and n = 1.
40. (a) Riddell, F. G.; Hayer, M. K. Biochim. Biophys. Acta 1985, 817, 313-317.
41. (b) Buster, D. C.; Hinton, J. F.; Millett, F. S.; Shungu, D. C. Biophys. J. 1988, 53, 145-152.
42. (c) Riddell, F. G.; Arumugam, S.; Brophy, P. J.; Cox, B. G.; Payne, M. C. H.; Southon, T. E. J. Am. Chem. Soc. 1988, 110, 734-738.
43. (d) Riddell, F. G.; Arumugam, S. Biochim. Biophys. Acta 1989, 984, 6-10.
44. (e) Riddell, F. G.; Tompsett, S. J. Biochim. Biophys. Acta 1990, 1024, 193-197.
45. Lamb, J. D.; Christensen, J. J.; Izatt, S. R.; Bedke, K.; Astin, J. S.; Izatt, R. M. J. Am. Chem. Soc. 1980, 102 (10), 3399.
46. (b) Lamb, J. D.; Izatt, R. M.: Garrick, D. G.; Bradshaw, J. S.; Christensen, J. J. J. Membr. Sci. 1981, 9, 83-107.
47. Chloroform (6 mL) was used as the bulk membrane membrane. The source phase was aqueous sodium picrate (1 mM) in the presence of excess NaOH (100 mM). The receiving phase was initially distilled, deionized water. Aliquots were withdrawn at the specified intervals and analyzed by UV-visible spectroscopy.
48. (a) Kumpf, R. A.; Dougherty, D. A. Science 1993, 261, 1708.
49. (b) Dougherty, D. A. Science 1996, 271, 163-167.
50. Taft, R. W. J. Phys. Chem. 1960, 64, 1805.