The C-and N-terminal residues of synthetic heptapeptide ion channels influence transport efficacy through phospholipid bilayers

New Journal of Chemistry

Volumn 29, Issue 2, 2005, Pages 291-305

  Djedovič, Natasha ^a   Ferdani, Riccardo ^a   Harder, Egan ^a   Pajewska, Jolanta ^a   Pajewski, Robert ^a   Weber, Michelle E ^a   Schlesinger, Paul H ^a   Gokel, George W ^a  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; AMIDE; ANION CHANNEL; BENZYL DERIVATIVE; CHLORIDE; ESTER; HEPTAPEPTIDE; ION CHANNEL; POTASSIUM;

AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; ION TRANSPORT; MEMBRANE TRANSPORT; PHOSPHOLIPID BILAYER; PRIORITY JOURNAL;

EID: 14644388120     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b417091c     Document Type: Article

References (69)

1. (a) D. J. Aidley. P. R. Stanfield, Ion Channels: Molecules in Action, Cambridge University Press, Cambridge, 1996;
2. (b) B. Hille, Ionic Channels of Excitable Membranes, 3rd Edn., Sinauer Associates, Sunderland MA, 2001.
3. (a) D. A. Doyle, J. M. Cabral, R. A. Pfuetzner, A. Kuo, J. M. Gulbis, S. L. Cohen, B. T. Chait and R. MacKinnon, Science, 1998, 280, 69-77;
4. (b) R. MacKinnon, S. L. Cohen, A. Kuo, A. Lee and B. T. Chait, Science, 1998, 280, 106-109.
5. C. Sato, Y. Ueno, K. Asai, K. Takahashi, M. Sato, A. Engel and Y. Fujiyoshi, Nature, 2001, 409, 1047-1051.
6. (a) R. Dutzler, E. B. Campbell, M. Cadene, B. T. Chait and R. MacKinnon, Nature, 2002, 415, 287-294;
7. (b) R. Dutzler, E. B. Campbell and R. MacKinnon, Science, 2003, 300, 108-112.
8. (a) G. M. Preston, T. P. Carroll, W. B. Guggino and P. Agre, Science, 1992, 256, 385-387;
9. (b) M. Borgnia, S. Nielsen, A. Engel and P. Agre, Annu. Rev. Biochem., 1999, 68, 425-458;
10. (c) G. Hummer, J. C. Rasalah and J. P. Noworyta, Nature, 2001, 414, 188-190.
11. (a) G. Chang, R. H. Spencer, A. T. Lee, M. T. Barclay and D. C. Rees, Science, 1998, 282, 2220-2226;
12. (b) R. H. Spencer, G. Chang and D. C. Rees, Curr. Opin. Struct. Biol., 1999, 9, 448-454;
13. (c) J. N. Scarsdale, G. Kazanina, X. He, K. A. Reynolds and H. T. Wright, J. Biol. Chem., 2001, 276, 20516-20522.
14. P. Agre, Angew. Chem. Int. Ed., 2004, 43. 4278-4290.
15. R. MacKinnon, Angew. Chem. Int. Ed., 2004, 43, 4265-4277.
16. (a) R. N. Reusch and H. L. Sadoff, Proc. Natl. Acad. Sci. USA, 1988, 85, 4176-4180;
17. (b) R. N. Reusch, R. Huang and L. L. Bramble, Biophys. J., 1995, 69, 754-766.
18. (a) D. Seebach, A. Brunner, H. M. Buerger, R. N. Reusch and L. L. Bramble, Helv. Chim. Acta, 1996, 79, 507-517;
19. (b) S. Das, U. D. Lengweiler, D. Seebach and R. N. Reusch, Proc. Natl. Acad. Sci. USA, 1997, 94, 9075-9079.
20. (a) S. Oiki, W. Danho and M. Montal, Proc. Natl. Acad. Sci. USA. 1988, 85, 2393-2397;
21. (b) M. Montal, M. S. Montal and J. M. Tomich, Proc. Natl. Acad. Sci. USA, 1990, 87, 6929-6933.
22. (a) T. Iwamoto, A. Grove, M. O. Montal, M. Montal and J. M. Tomich, Int. J. Pept. Protein Res., 1994, 43, 597-607;
23. (b) M. Montal, Annu. Rev. Biophys. Biomol. Struct., 1995, 24, 31-57.
24. (a) J. D. Lear, Z. R. Wasserman and W. F. DeGrado, Science, 1988, 240, 1177-1181;
25. (b) W. F. DeGrado, Z. R. Wasserman and J. D. Lear, Science, 1989, 243, 622-628.
26. (a) K. S. Åkerfeldt, J. D. Lear, Z. R. Wasserman, L. A. Chung and W. F. DeGrado, Acc. Chem. Res., 1993, 26, 191-197;
27. (b) G. R. Dieckmann and W. F. DeGrado, Curr. Opin. Struct. Biol., 1997, 7, 486-494.
28. I. Tabushi, Y. Kuroda and K. Yokota, Tetrahedron Lett., 1982, 4601-4604.
29. 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.
30. L. Jullien and J.-M. Lehn, Tetrahedron Lett., 1988, 3803-3806.
31. F. M. Menger, D. S. Davis, R. A. Persichetti and J.-J. Lee, J. Am. Chem. Soc., 1990, 112, 2451-2452.
32. (a) A. J. M. v. Beijnen, R. J. M. Nolle, J. W. Zwikker and W. Drenth, Recl. Trav. Pays-Bas, 1982, 101, 409-410;
33. (b) M. F. M. Roks and R. J. M. Nolle, Macromolecules, 1992, 25, 5398-5407.
34. Y. Kobuke, K. Ueda and M. Sokabe, J. Am. Chem. Soc., 1992, 114, 7618-7822.
35. A. Nakano, Q. Xie, J. V. Mallen, L. Echegoyen and G. W. Gokel, J. Am. Chem. Soc., 1990, 112, 1287-1289.
36. J.-C. Meillon and N. Voyer, Angew. Chem., Int. Ed. Engl, 1997, 36, 967-969.
37. N. Sakai, C. Ni, S. M. Bezrukov and S. Matile, Bioorg. Med. Chem. Lett., 1998, 8, 2743-2746.
38. A. Schrey, A. Vescovi, A. Knoll, C. Rickerl and U. Koerl, Angew. Chem. Int. Ed., 2000, 39, 900-902.
39. (a) G. W. Gokel and O. Murillo, Acc. Chem. Res., 1996, 29, 425-432;
40. (b) G. W. Gokel and A. Mukhopadhyay, Chem. Soc. Rev., 2001, 30, 274-286.
41. J. M. Boon and B. D. Smith, Curr. Opin. Chem. Biol., 2002, 6, 749-756.
42. T. W. Bell, Curr. Opin. Chem. Biol, 1998, 2, 711-716.
43. N. Sakai and S. Matile, Chem. Commun., 2003, 2514-2523.
44. A. Bianchi, K. Bowman-James and E. Garcia-España, Supramolecular Chemistry of Anions, Wiley-VCH, New York, 1997.
45. (a) D. P. Wallace, J. M. Tomich, J. W. Eppler, T. Iwamoto, J. J. Grantham and L. P. Sullivan, Biochim. Biophys. Acta, 2000, 1464, 69-82;
46. (b) J. R. Broughman, K. E. Mitchell, R. L. Sedlacek, T. Iwamoto, J. M. Tomich and B. D. Schultz, Am. J. Physiol., 2001, 280, C451-C458;
47. (c) L. Gao, J. R. Broughman, T. Iwamoto, J. M. Tomich, C. J. Venglarik and H. J. Forman, Am. J. Physiol., 2001, 281, L24-L30.
48. V. Sidorov, F. W. Kotch, J. L. Kuebler, Y.-F. Lam and J. T. Davis, J. Am. Chem. Soc., 2003, 125, 2840-2841.
49. (a) P. H. Schlesinger, R. Ferdani, J. Liu, J. Pajewska, R. Pajewski, M. Saito, H. Shabany and G. W. Gokel, J. Am. Chem. Soc., 2002, 124, 1848-1849;
50. (b) P. H. Schlesinger, R. Ferdani, R. Pajewski, J. Pajewska and G. W. Gokel, Chem. Commun., 2002, 840-841;
51. (c) P. H. Schlesinger, N. K. Djedovic, R. Ferdani, J. Pajewska, R. Pajewski and G. W. Gokel, Chem. Commun., 2003, 308-309;
52. (d) P. H. Schlesinger, R. Ferdani, J. Pajewska, R. Pajewski and G. W. Gokel, New J. Chem., 2003, 27, 60-67.
53. N. Sakai, D. Houdebert and S. Matile, Chemistry. 2003, 9, 223-232.
54. G. W. Gokel, Chem. Commun., 2000, 1-9.
55. J. Bolard, Biochim. Biophys. Acta, 1986, 864, 257-304.
56. J. Zhou, X. Lu, Y. Wang and J. Shi, Fluid Phase Equilib., 2002, 194-197, 257-270.
57. M. Hervé, B. Cybulska and C. M. Gary-Bobo, Eur. Biophys. J., 1985, 12, 121-128.
58. (a) 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;
59. (b) T. M. Fyles, T. D. James and K. C. Kaye, J. Am. Chem. Soc., 1993, 115, 12315-12321.
60. F. G. Riddell and S. J. Tompsett, Biochim. Biophys. Acta, 1990, 990, 193-197.
61. O. Murillo, S. Watanabe, A. Nakano and G. W. Gokel, J. Am. Chem. Soc., 1995, 117, 7665-7679.
62. M. Saito, S. J. Korsmeyer and P. H. Schlesinger, Nature Cell Biol., 2000, 553-555.
63. A. V. Koulov, T. N. Lambert, R. Shukla, M. Jain, J. M. Boon, B. D. Smith, H. Li, D. N. Sheppard, J. B. Joos, J. P. Clare and A. P. Davis, Angew. Chem. Int. Ed., 2003, 42, 4931-4933.
64. A. S. Ladokhin, M. E. Selsted and S. H. White, Biophys. J., 1997, 72, 1762-1766.
65. J. C. Hernandez, J. E. Trafton and G. W. Gokel, Tetrahedron Lett., 1991, 6269-6272.
66. H. W. Huang, F.-Y. Chen and M.-T. Lee, Phys. Rev. Lett., 2004, 92, 198304/1-198304/4.
67. J. C. Stewart, Anal. Biochem., 1980, 104, 10-14.
68. F. Szoka and D. Papahadjopoulos, Proc. Natl. Acad. Sci. USA, 1978, 75, 4194-4198.
69. S. Rex and G. Schwarz, Biochemistry, 1998, 37, 2336-2345.