Toward biomimetic ion channels formed by rigid-rod molecules: Length-dependent ion-transport activity of substituted oligo(p-phenylene)s

Journal of the American Chemical Society

Volumn 119, Issue 37, 1997, Pages 8726-8727

  Sakai, Naomi ^a   Brennan, Kevin C ^a   Weiss, Linnea A ^a   Matile, Stefan ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOTERICIN B; ION CHANNEL;

ARTICLE; DRUG STRUCTURE; FLUORESCENCE; ION TRANSPORT; LIPID BILAYER; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOISOMERISM;

EID: 0030931384     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971513h     Document Type: Article

References (35)

1. (a) Bolard, J. Biochim. Biophys. Acta 1985, 864, 257. Recent leading references include:
2. (b) Yamashita, K.; Janout, V.; Bernard, E. M.; Armstrong, D.; Regen, S. L. J. Am. Chem. Soc. 1995, 117, 6249.
3. Stadler, E.; Dedek, P.; Yamashita, K.; Regen, S. L. J. Am. Chem. Soc. 1994, 116, 6677.
4. Bolard, J.; Legrand, P.; Heitz, F.; Cybulska, B. Biochemistry 1991, 30, 5707.
5. For other nonpeptide natural products and their analogues of interest see: (a) Sakai, N.; Matile, S. Tetrahedron Lett. 1997, 38, 2613.
6. (b) Matile, S.; Nakanishi, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 757.
7. Deng, G.; Dewa, T.; Regen, S. L. J. Am. Chem. Soc. 1996, 118, 8975.
8. Gokel, G. W.; Murillo, O. Ace. Chem. Res. 1996, 29, 425.
9. Milon, A.; Wolff, G.; Ourisson, G.; Nakatani, Y. Heb. Chim. Acta 1986, 69, 12.
10. 6 rigid-rod molecules have attracted a great deal of attention for the preparation of novel materials and as spacers to probe intramolecular interactions. Selected recent references:
11. (a) Maddux, T.; Li, W.; Yu, L. J. Am. Chem. Soc. 1997, 119, 844.
12. (b) Nuding, G.; Vögtle, F.; Danielmeier, K.; Steckhan, E. Synthesis 1996, 71.
13. Li, W.; Fox, M. A. J. Am. Chem. Soc. 1996, 118, 11752.
14. Ayres, F. D.; Khan, S.; Chapman, O. L. Tetrahedron Lett. 1994, 35, 8561.
15. (e) Eaton, P. E.; Galoppini, E.; Gilardi, R. J. Am. Chem. Soc. 1994, 116, 7588.
16. (f) Kaszynski, P.; Friedli, A. C.; Michl, J. J. Am. Chem. Soc. 1992, 114, 601.
17. (g) Yang, X.; Jiang, W.; Knobler, C. B.; Hawthorne, M. F. J. Am. Chem. Soc. 1992, 114, 9719.
18. (h) Feldman, K. S.; Bobo, J. S.; Ensel, S. M.; Lee, Y. B.; Weinreb, P. H. J. Org. Chem. 1990, 55, 474.
19. Lehn, J.-M. In Frontiers in Supramolecular Organic Chemistry and Photochemistry; Schneider, H.-J., Dürr, H., Eds.; VCH: Weinheim, 1991; pl.
20. Some pertinent references on oligo(p-phenylene)s: (a) Rajca, A.; Safronov, A.; Rajca, S.; Shoemaker, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 448.
21. (b) Keegstra, M. A.; De Feyter, S.; De Schryver, F.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 775.
22. Baker, K. N.; Fratini, A. V.; Resch, T.; Knachel, H. C.; Adams, W. W.; Socci, E. P.; Farmer, B. L. Polymer 1993, 34, 1571.
23. Rinke, M.; Gusten, H.; Ache, H. J. J. Phys. Chem. 1985, 90, 2661.
24. (e) Heitz, W.; Ullrich, R. Makromol. Chem. 1966, 98, 29.
25. Miyaura, N.; Yanagi, T.; Suzuki, A. Synlh. Commun. 1981, 11, 513.
26. (a) Caffrey, M.; Feigenson, G. W. Biochemistry 1981, 20, 1949.
27. (b) Kleinfeld, A. M. Curr. Top. Membr. Transp. 1987, 29, 1.
28. (a) Zumbühl, O.; Weder, H. G. Biochim. Biophys. Acta 1981, 640, 252.
29. (b) Mimms, L. T.; Zampighi, G.; Nozaki, Y.; Tanford, C; Reynolds, J. A. Biochemistry 1981, 20, 833.
30. (a) Venema, K.; Gibrat, R.; Grouzis, J.-P.; Grignon, C. Biochim. Biophys. Acta 1993, 1146, 87.
31. (b) Kano, K.; Pendler, J. H. Biochim. Biophys. Acta 1978, 509, 289.
32. The corresponding octamethoxy derivative 10 and octaphenol 15 were completely inactive; octaacetonide 18 had minor activity.
33. + selectivity and not as a detergent-like defect inducer; dye-release experiments fully corroborate the latter implication.
34. Hervé, M.; Cybulska, B.; Gary-Bobo, C. M. Eur. Biophys. J. 1985, 12, 121.
35. Leo, A. J. Methods Enzymol. 1991, 202, 544.