Synthetic Organic Chemical Models for Transmembrane Channels

Accounts of Chemical Research

Volumn 29, Issue 9, 1996, Pages 425-432

  Gokel, George W ^{a,b,c,d,e,f,g,h}   Murillo, Oscar ^a,i,j  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b TULANE UNIVERSITY   (United States)

^c UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^d DUPONT COMPANY   (United States)

^e PENNSYLVANIA STATE UNIVERSITY   (United States)

^f UNIVERSITY OF MIAMI   (United States)

^g School of Medicine ^*

^h Bioorganic Chemistry Program

ⁱ UNIVERSIDAD DE COSTA RICA   (Costa Rica)

^j Department of Biology

more..

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000391995     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar9601353     Document Type: Article

References (79)

1. Läuger, P. Angew. Chem., Int. Ed. Engl. 1985, 24, 905-923.
2. Stryer, L. Biochemistry, 2nd ed.; Freeman: New York, 1981; pp 205-218.
3. Hille, B. Ionic Channels of Excitable Membranes, 2nd ed.; Sinauer: Sunderland, MA, 1992; p 1.
4. (a) Henderson, R.; Baldwin, J. M.; Ceska, T. A.; Zemlin, F.; Beckmann, E.; Downing, K. H. J. Mol. Biol. 1990, 213, 899-929.
5. (b) Deisenhofer, J.; Epp, O.; Miki, K.; Huber, R.; Michel, H. Nature 1985, 318, 618-624.
6. Brisson, A.; Unwin, P. N. T. Nature 1985, 315, 474-477.
7. Noda, M.; et al. Nature 1984, 312, 121-127.
8. Hille, B. Ionic Channels of Excitable Membranes, 2nd ed.; Sinauer: Sunderland, MA, 1992; pp 244-245.
9. Hucho, F.; G'rne-Tschelnokow, U.; Strecker, A. TIBS 1994, 383-387.
10. Bolard, J. Biochim. Biophys. Acta 1986, 864, 257-304.
11. (a) Urry, E. W., Goodall, M. C., Glickson, J. D., Meyers, D. F Proc. Natl. Acad. Sci. U.S. A. 1971, 68, 1907-1911.
12. (b) Urry, D. W. Proc. Natl. Acad. Sci. U.S.A 1971, 68, 672-676.
13. Muller, M.; Rudin, D. O. Nature 1968, 217, 713-719.
14. Woolley, G. A.; Wallace, B. A. J. Membr. Biol. 1992, 129, 109-136.
15. Gennis, R. B. Biomembranes: Molecular Structure and Function; Springer-Verlag: New York, 1988; p 286.
16. (a) Wallace, B. A. Annu. Rev. Biophys. Biophys. Chem. 1990, 19, 127-57.
17. (b) Killiam, J. A. Biochim. Biophys. Acta 1992, 1113, 391-425.
18. (a) Wallace, B. A., Ravikumar, K. Science 1988, 241, 182-187.
19. (b) Langs, D. Science 1988, 241, 188-191.
20. Läuger, P.; Bamberg, E. J. Membr. Biol. 1977, 35, 351-75.
21. Urry, D.; Spisni, A.; Khaled, M. Biochem. Biophys. Res. Commun. 1979, 88 (3), 940-949.
22. Wooley, G. A.; Wallace, B. A. Membr. Biol. 1992, 129, 109-136.
23. Grove, A.; Mutter, M.; Rivier, J. E.; Montal, M. J. Am. Chem. Soc. 1993, 115, 5919-5924.
24. (a) Vuilleumier, E. S.; Fritz, H.; Mutter, M. Tetrahedron Lett. 1990, 31 (28), 4015-4018.
25. (b) Mutter, M.; et al. J. Am. Chem. Soc. 1992, 114, 1463-1470.
26. Lear, J. D.; Wasserman, Z. R.; DeGrado, W. F. Science 1988, 240, 1177-1181.
27. Ckerfeldt, K.; Lear, J. D.; Wasserman, Z. R.; Chung, L. A.; DeGrado, W. F. Acc. Chem. Res. 1993, 26, 191-197.
28. Tabushi, I., Kuroda, Y., Yokota, K. Tetrahedron Lett. 1982, 23 (44), 4601-4604.
29. The three hydroxylated carbons of glycerol in lipids are designated sn-1 to sn-3. The chiral carbon is sn-2, and the lipid head group is located at sn-3.
30. Menger, F. M.; Davis, D. S.; Persichetti, R. A.; Lee, J. J. J. Am. Chem. Soc. 1990, 112, 2451-2452.
31. Kano, K.; Fendler, J. H. Biochim. Biophys. Acta 1978, 509, 289.
32. (a) Kumpf, R. A.; Dougherty, D. A. Science 1993, 261, 1708.
33. (b) Dougherty, D. A. Science 1996, 271, 163-167.
34. Kobuke, Y.; Ueda, K; Sokabe, M. J. Am. Chem. Soc. 1992, 114, 7618-7620.
35. (a) Neevel, J. G.; Nolte, R. Tetrahedron Lett. 1984, 25(21), 2263-2266.
36. (b) Nolte, R. J. M.: Beijnen A. J. M.; Neevel, J. G.; Zwikker, J. W.; Verkley, A. J.; Drenth, W. Isr. J. Chem. 1984, 24, 297-301.
37. (c) Kragten, U. F.; Roks, M. F. M.; Nolte, R. J. M. J. Chem. Soc., Chem. Commun. 1985, 1275-1276.
38. (a) Fuhrhop, J. H.; Liman, U.; David, H. H. Angew. Chem., Int. Ed. Engl. 1985, 24 (4), 339-340.
39. (b) Fuhrhop, J. H.; Liman, U.; Koesling, V. J. Am. Chem. Soc. 1988, 110, 6840-6845.
40. Voyer, N.; Robitaille, M. J. Am. Chem. Soc. 1995, 117, 6599-6600.
41. (a) Stankovic, C.; Heinemann, S.; Delfino, J.; Sigworth, F.; Schreiber, S. L. Science 1989, 24, 813-817.
42. (b) Stankovic, C.; Heinemann, S. H.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 3702-3704.
43. (c) Stankovic, C.; Schreiber, S. L. Chemtracts:Org. Chem. 1991, 4, 1-20.
44. (d) Stankovic, C.; Heinemann, S. H.; Schreiber, S. L. Biochim. Biophys. Acta 1991, 1061, 163-170.
45. (a) Jullien, L.; Lehn, J. Tetrahedron Lett. 1988, 29, 3803-3806.
46. (b) Jullien, L.; Lehn, J. M. J. Inclusion Phenom. 1992, 12, 55-74.
47. (a) Carmichel, V. E.; Dutton, P.; Fyles, T.; James, T.; Swan, J.; Zojaji, M. J. Am. Chem. Soc. 1989, 111, 767-769.
48. (b) Fyles, T.; James, T.; Kaye, K. Can. J. Chem. 1990, 68, 976-978.
49. (c) Fyles, T.; Kaye, K.; James, T.; Smiley, D. Tetrahedron Lett. 1990, 1233.
50. (d) Kaye, K.; Fyles, T. J. Am. Chem. Soc. 1993, 115, 12315-12321.
51. (e) Fyles, T.; James, T.; Pryhitka, A.; Zojaji, M. J. Org. Chem. 1993, 58, 7456-7468.
52. McLaughlin, S.; Eisenberg, M. Annu. Rev. Biophys. Bioeng. 1975, 4, 335.
53. FCCP is carbonyl cyanide [4-(trifluoromethoxy)phenyl]hydrazone.
54. Hervé, M.; Cybulska, B.; Gary-Bobo, C. M. Eur. Biophys. J. 1985, 12, 121.
55. (a) Canceill, J.; Jullien, L.; Lacombe, L.; Lehn, J. M. Helv. Chim. Acta 1992, 75, 791-811.
56. (b) Pregel, M.; Jullien, L.; Lehn, J. M. Angew. Chem., Int. Ed. Engl. 1992, 31, 1637-1639.
57. (c) Pregel, M.; Jullien, L.; Canceill, J.; Lacombe, L.; Lehn, J.M, J. Chem. Soc., Perkin Trans. 2 1995, 417-426.
58. Stadler, E.; Dedek, P.; Yamashita, K.; Regen, S. J. Am. Chem. Soc. 1994, 116, 6677-6682.
59. Nakano, A.; Xie, Q.; Mallen, J.; Echegoyen, L.; Gokel, G. W. J. Am. Chem. Soc. 1990, 112, 1287.
60. (a) Kuwamura, T.; Kawachi, T. Yukagaku 1979, 28, 195.
61. (b) Kuwamura, T.; Akimary, M.; Takahashi, H. L.; Arai, M. Kenkyu Hokoku-Asahi Garasu Kogyo Gijutsu Shorekai 1979, 35, 45.
62. (c) Kuwamura, T.; Yoshida, S. Nippon Kagaku Kaishi 1980, 427.
63. (a) Okahara, M.; Kuo, P. L.; Yamamura, S.; Ikeda, I. J. Chem. Soc., Chem. Commun. 1980, 586.
64. (b) Ikeda, I.; Iwaisako, K.; Nakatsuji, Y.; Okahara, M. Yukagaku 1979, 28, 195.
65. (a) Echegoyen, L. E.; Portugal, L.; Miller, S. R.; Hernandez, J. C.; Echegoyen, L.; Gokel, G. W. Tetrahedron Lett. 1988, 29, 4065-4068.
66. (b) Fasoli, H.; Echegoyen, L. E.; Hernandez, J. C.; Gokel, G. W.; Echegoyen, L. J. Chem. Soc., Chem. Commun. 1989, 578-580.
67. (c) Muñoz, S.; Mallén, J. V.; Nakano, A.; Chen, Z.; Echegoyen, L.; Gay, I.; Gokel, G. W. J. Chem. Soc., Chem. Commun. 1992, 520-522.
68. (d) Muñoz, S.; Mallén, J.; Nakano, A.; Chen, Z.; Gay, I.; Echegoyen, L.; Gokel, G. W. J. Am. Chem. Soc. 1993, 115, 1705-1711.
69. Liesegang, G. W.; Farrow, M. M.; Arce Vazquez, F.; Pudie, N.; Eyring, E. M. J. Am. Chem. Soc. 1977, 99, 3240-3243.
70. Riddell, F.; Hayer, M. Biochim. Biophys. Acta 1985, 817, 313-317.
71. Buster, D.; Hinton, J.; Millett, F.; Shungu, D. Biophys. J. 1988, 53, 145-152.
72. Hernandez, J. C.; Trafton, J. E.; Gokel, G. W. Tetrahedron Lett. 1991, 6269-6272.
73. Murillo, O.; Watanabe. S.; Nakano, A.; Gokel, G. W. J. Am. Chem. Soc. 1995, 117, 7665-7679.
74. Murillo, O.; Suzuki, I.; Abel, E.; Gokel, G. W. J. Am. Chem. Soc., in press.
75. Abel, E.; Fedders, M. F.; Gokel, G. W. J. Am. Chem. Soc. 1995, 117, 1265-1270.
76. (a) Ghadiri, M. R., Granja, J. R., Buehler, L. K. Nature 1994, 369, 301-304.
77. (b) Khazanovich, N., Granja, J. R., McRee, D. E., Milligan, R. A., Ghadiri, M. R. J. Am. Chem. Soc. 1994, 116, 6011-6012.
78. Tanaka, Y.; Kobuke, Y.; Sokabe, M. Angew. Chem., Int. Ed. Engl. 1995, 34(6), 693-694.
79. Gokel, G. W.; Medina, J. C.; Li, C. Synlett 1991, 677-683.