Bioorganic chemistry àla baguette: Studies on molecular recognition in biological systems using rigid-rod molecules

Chemical Records

Volumn 1, Issue 2, 2001, Pages 162-172

  Matile, Stefan ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Host guest complexes; Ion channels; Molecular recognition; Oligomers; Peptidomimetics

Indexed keywords

BENZENE DERIVATIVE; CELL SURFACE RECEPTOR; ION CHANNEL; IONOPHORE; LIGAND;

CELL MEMBRANE; CHEMISTRY; CONFORMATION; ION TRANSPORT; LIPID BILAYER; METABOLISM; MOLECULAR PROBE; REVIEW; ULTRASTRUCTURE;

BENZENE DERIVATIVES; CELL MEMBRANE; ION CHANNELS; ION TRANSPORT; IONOPHORES; LIGANDS; LIPID BILAYERS; MOLECULAR CONFORMATION; MOLECULAR PROBES; RECEPTORS, CELL SURFACE;

EID: 0000124227     PISSN: 15278999     EISSN: None     Source Type: Journal    
DOI: 10.1002/tcr.6     Document Type: Article

References (83)

1. Schwab, P.F.H.; Levin, M.D.; Michl, J. Chem Rev 1999, 99, 1863.
2. Martin, R.E.; Diederich, F. Angew Chem Int Ed 1999, 38, 1351.
3. Müllen, K.; Wegner, G. Electronic Materials: The Oligomer Approach; Wiley: Weinheim, 1998.
4. Tour, J.M. Chem Rev 1996, 96, 537.
5. Ringsdorf, H.; Schlarb, B.; Venzmer, J. Angew Chem Int Ed Engll988,27, 113.
6. Ghebremariam, B.; Sidorov, V.; Matile, S. Tetrahedron Lett 1999,40, 1445.
7. Sidorov, V.; Douglas, T.; Dzenukov, S. M.; Abdallah, D.; Ghebremariam, B.; Roepe, P.D.; Matile, S. Chem Commun 1999, 1429
8. Winum, J.-Y.; Matile, S. J Am Chem Soc 1999, 121,7961.
9. Sakai, N.; Matile, S. Chem Eur J 2000, 6, 1731.
10. Robert, F.; Winum, J.-Y.; Sakai, N.; Gérard, D.; Matile, S. Org Lett 2000, 2, 37.
11. Weiss, LA.; Sakai, N.; Ghebremariam, B.; Ni, C; Matile, S. J Am Chem Soc 1997, 119, 12142.
12. Ni, C; Matile, S. Chem Commun 1998, 755.
13. Sakai, N.; Brennan, K.C.; Weiss LA.; Matile, S. J Am Chem Soc 1997, 119,8726.
14. Sakai, N.; Ni, C.; Bezrukov, S. M.; Matile, S. Bioorg Med Chem Lett 1998, 8, 2743.
15. Tedesco, M.M.; Ghebremariam, B.; Sakai, N.; Matile, S. Angew Chem Int Ed 1999, 38, 540.
16. [ 16] Ghebremariam, B.; Matile, S. Tetrahedron Lett 1998,39, 5335.
17. Ghebremariam, B.; Matile, S. Enantiomer 1999, 4, 121 and 131.
18. Tedesco, M.M.; Ghebremariam, B.; Matile, S. Colloids Surfaces A, Physiochem Eng Asp 2000, 169, 5.
19. Baumeister, B.; Sakai, N.; Matile, S. Angew Chem Int Ed 2000, 39, 1955.
20. Baumeister, B.; Matile, S. Chem Eur J 2000, 6, 1739.
21. Sakai, N.; Majumdar, N.; Matile, S. J Am Chem Soc 1999, 121,4294.
22. Sakai, N.; Baumeister, B.; Matile, S. Chem Bio Chem 2000, l, 123.
23. Baumeister, B.; Matile, S. Chem Commun 2000, 913.
24. Baumeister, B.; de Dios, A.C.; Matile, S. Tetrahedron Lett 1999, 40, 4623.
25. Chen, L.; Sakai, N.; Moshiri, S.T.; Matile, S. Tetrahedron Lett 1998,39,3627.
26. Suzuki, A. J Organomet Chem 1999, 576, 147.
27. Alberts, B.; Bray, D.; Lewis, J.; Raff, M.; Roberts, K.; Watson, J.D. Molecular Biology of the Cell, 3rd Ed.; Garland Publishing, Inc.: New York, 1994.
28. Ourisson, G.; Nakatani, Y. Chem Biol 1994, 1,11.
29. Matile, S.; Nakanishi, K. Angew Chem Int Ed Engl 1996, 35, 757.
30. Otto, S.; Osifchin, M; Regen, S.L.J Am Chem Soc 1999, 121, 7276 and 10440.
31. Bolard, J. Biochim Biophys Acta 1986, 864, 257.
32. Gabay, J.D. Science 1994, 264, 373.
33. Nikaido, H. Science 1994, 264, 382.
34. Killian, J.A. Biochim Biophys Acta 1998, 1376, 401.
35. Fattal, D.R.; Ben-Shaul, A. Biophys J 1993, 65, 1795
36. Tedesco, M.M.; Ghebremariam, B.; Matile, S. Unpublished results.
37. Tabushi, I.; Kuroda, Y.; Yokota, K. Tetrahedron Lett 1982, 23, 4601
38. Koert, U. Chem Unserer Z 1997, 31, 20.
39. Gokel, G.W.; Murillo, O. Ace Chem Res 1996, 29, 425.
40. Fyles, T.M.; van Straaten-Nijenhuis, W.F. Comprehensive Supramolecular Chemistry Vol. 10, Reinhouldt, N. D. editor; Elsevier: Oxford, 1996; p 53.
41. Voyer, N. Top Curr Chem 1996, 184, 1.
42. Tanaka, Y.; Kobuke, Y.; Sokabe, M. Angew Chem Int Ed Engl 1995,34,693.
43. Fyles, T.M.; Loock, D.; Zhou, X. J Am Chem Soc 1998, 120, 2997.
44. Lear, J.D.; Schneider, J.P.; Kienker, P.K.; DeGrado, W.F. J Am Chem Soc 1997, 119,3212.
45. Fyles, T.M.; Zeng, B. Chem Commun 1996, 2295.
46. Fritz, M.G.; Walde, P.; Seebach, D. Macromolecules 1999,32,574.
47. Qi, Z.; Sokabe, M.; Donowaki, K.; Ishida, H. Biophys J 1999, 76,631.
48. Hall, C.D.; Kirkovits, G.J.; Hall, A.C. Chem Commun 1999, 1897.
49. Nagle, J.F.; Tristram-Nagle, S. J Membr Biol 1983, 74, 1.
50. Dougherty, D. A. Science 1996, 271, 163.
51. Kumpf, R.A.; Dougherty, D.A. Science 1993, 261, 1092.
52. Doyle, D.A.; Cabrai, J.M.; Pfuetzner, R.A.; Kuo, A.; Gulbis, J.M.; Cohen, S.L.; Chait, B.T.; MacKinnon, R. Science 1998, 280, 69.
53. Ikeda, A.; Shinkai, S. Chem Rev 1977, 97, 1713.
54. Eisenman, G.; Horn, R. J Membr Biol 1983, 76, 197.
55. Malone, K.M.; Shnek, D.R.; Sasaki, t>.Y; Arnold, F.H. Chem Biol 1996,3, 185.
56. Richardson, J.S. Nature 1997, 268, 495.
57. Flower, D.R. Biochem J 1996, 318, 1.
58. Beste, G.; Schmidt, F.S.; Stibora, T.; Skerra, A. Proc Natl Acad Sei USA 1999, 96, 1898.
59. Barbas III., C.F.; Heine, A.; Zhong, G.; Hoffmann, T.; Gramatikova, S.; Björnestedt, R.; List, B.; Anderson, J.; Stura, E.A.; Wilson, I.A.; Lerner, R.A. Science 1997, 278, 2085.
60. Gu, L.-Q.; Braha, O.; Conlan, S.; Cheley, S.; Bayley, H. Nature 1999, 398, 686.
61. [61 ] Babbitt, P.C.; Gerlt, J.A. J Biol Chem 1997, 272, 30591.
62. Schneider, J.P.; Kelly, J.W. Chem Rev 1995, 95, 2169.
63. Ma, K.; Clancy, E.L.; Zhang, Y; Ray, D.G.; Wollenberg, K.; Zagorsky, M.G. J Am Chem Soc 1999, 121, 8698.
64. Smith, C.K.; Regan, L. Ace Chem Res 1997, 30, 153.
65. Nowick, J.S. Ace Chem Res 1999, 32, 287.
66. Lawrence, D.S.; Jiang.T.; Levett, M. Chem Rev 1995,95,2229.
67. Aoyagi, M.; Biradha, K.; Fujita, M. J Am Chem Soc 1999, 121,7457.
68. Ghadiri, M.R.; Granja, J. R.; Buehler, L.K. Nature 1994,369,301.
69. Venkataraman, D.; Lee, S.; Zhang, J.; Moore, J. S. Nature 1994, 271,591.
70. Harada, A.; Li, J.; Kamachi, M. Nature 1993, 289, 516.
71. Ranganathan, D.; Lakshimi, C.; Karle, I.L. J Am Chem Soc 1999,121,6103.
72. Breslow, R. Ace Chem Res 1995, 28, 146.
73. Gutsche, C.D. Calixarenes; The Royal Society of Chemistry: Cambridge, 1991.
74. Diederich, F. Cyclophanes; The Royal Society of Chemistry: Cambridge, 1991.
75. Kim, J.; Jung, I.-S.; Kim, S.-Y.; Lee, E.; Kang, J.-K.; Sakamoto, J.-K.; Yamaguchi, K.; Kim, K. J Am Chem Soc 2000, 122, 540.
76. Song, X.; Geiger, C.; Leinhos, U.; Perlstein, J.; Whitten, D.G. J Am Chem Soc 1994, 116, 10340.
77. Whitesides, G.M.; Simanek, E.E.; Mathias, J.P.; Seto, C.T.; Chin, D.N.; Mammen, M.; Gordon, D.M. Ace Chem Res 1995, 28, 37
78. Daher, S.; Kimber, M.; Baumeister, B.; Sakai, N.; Matile, S. Unpublished results.
79. Behr, J.P. Acc Chem Res 1993, 26, 274.
80. Akeson, M.; Branton, D.; Kasianowicz, J.J.; Brandin, E.; Deamer, D.W. Biophys J 1999, 77, 3227.
81. de Gennes, P.-G. Proc Natl Acad Sei USA 1999, 96, 7262.
82. Sanders,]. K. M. Chem Eur J 1998, 4, 1378.
83. McQuade, D.T.; Quinn, M.A.; Yu, S.M.; Polans, A.S.; Krebs, M.P.; Gellman, S.H. Angew Chem Int Ed 2000, 39, 758.