On the electrostatics of cell-membrane recognition: From natural antibiotics to rigid push-pull rods

Chemistry - A European Journal

Volumn 6, Issue 10, 2000, Pages 1731-1737

  Sakai, Naomi ^a   Matile, Stefan ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Antibiotics; Ion channels; Membranes; Molecular recognition; Peptidomimetics

Indexed keywords

AMPHOTERICIN B; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT;

AMINO ACID SEQUENCE; ARTICLE; BILAYER MEMBRANE; CELL MEMBRANE; CHEMISTRY; DRUG STRUCTURE; ELECTRICITY; ION CHANNEL; MOLECULAR GENETICS; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; STRUCTURE ANALYSIS;

AMINO ACID SEQUENCE; ANTI-BACTERIAL AGENTS; ELECTROSTATICS; MOLECULAR SEQUENCE DATA;

EID: 0034660287     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(20000515)6:10<1731::aid-chem1731>3.3.co;2-%23     Document Type: Article

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38. Reviews on nonpeptide ion channels and channel models: a) U. Koert, Chem. Unserer Zeit 1997, 31, 20; b) G. W. Gokel, O. Murillo, Acc. Chem. Res. 1996, 29, 425; c) T. M. Fyles, W. F. van Straaten-Nijenhuis, in Comprehensive Supramoleculur Chemistry, Vol. 10 (Ed.: D. N. Reinhouldt), Elsevier, Oxford, 1996, p. 53; d) N. Voyer, Top. Curr. Chem. 1996, 184, 1; some more recent references: e) S. Otto, M. Osifchin, S. L. Regen, J. Am. Chem. Soc. 1999, 121, 10440; f) Z. Qi, M. Sokabe, K. Donowaki, H. Ishida, Biophys. J. 1999, 76, 631; g) E. Abel, E. M. Maguire, O. Murillo, I. Suzuki, S. L. DeWall, G. W. Gokel, J. Am. Chem. Soc. 1999, 121, 9043; h) M. G. Fritz, P. Walde, D. Seebach, Macromolecules 1999, 32, 574; i) J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, G. W. Gokel, Angew. Chem. 1998, 110, 1650; Angew. Chem. Int. Ed. 1998, 37, 1534.
39. Reviews on nonpeptide ion channels and channel models: a) U. Koert, Chem. Unserer Zeit 1997, 31, 20; b) G. W. Gokel, O. Murillo, Acc. Chem. Res. 1996, 29, 425; c) T. M. Fyles, W. F. van Straaten-Nijenhuis, in Comprehensive Supramoleculur Chemistry, Vol. 10 (Ed.: D. N. Reinhouldt), Elsevier, Oxford, 1996, p. 53; d) N. Voyer, Top. Curr. Chem. 1996, 184, 1; some more recent references: e) S. Otto, M. Osifchin, S. L. Regen, J. Am. Chem. Soc. 1999, 121, 10440; f) Z. Qi, M. Sokabe, K. Donowaki, H. Ishida, Biophys. J. 1999, 76, 631; g) E. Abel, E. M. Maguire, O. Murillo, I. Suzuki, S. L. DeWall, G. W. Gokel, J. Am. Chem. Soc. 1999, 121, 9043; h) M. G. Fritz, P. Walde, D. Seebach, Macromolecules 1999, 32, 574; i) J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, G. W. Gokel, Angew. Chem. 1998, 110, 1650; Angew. Chem. Int. Ed. 1998, 37, 1534.
40. Reviews on nonpeptide ion channels and channel models: a) U. Koert, Chem. Unserer Zeit 1997, 31, 20; b) G. W. Gokel, O. Murillo, Acc. Chem. Res. 1996, 29, 425; c) T. M. Fyles, W. F. van Straaten-Nijenhuis, in Comprehensive Supramoleculur Chemistry, Vol. 10 (Ed.: D. N. Reinhouldt), Elsevier, Oxford, 1996, p. 53; d) N. Voyer, Top. Curr. Chem. 1996, 184, 1; some more recent references: e) S. Otto, M. Osifchin, S. L. Regen, J. Am. Chem. Soc. 1999, 121, 10440; f) Z. Qi, M. Sokabe, K. Donowaki, H. Ishida, Biophys. J. 1999, 76, 631; g) E. Abel, E. M. Maguire, O. Murillo, I. Suzuki, S. L. DeWall, G. W. Gokel, J. Am. Chem. Soc. 1999, 121, 9043; h) M. G. Fritz, P. Walde, D. Seebach, Macromolecules 1999, 32, 574; i) J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, G. W. Gokel, Angew. Chem. 1998, 110, 1650; Angew. Chem. Int. Ed. 1998, 37, 1534.
41. Reviews on nonpeptide ion channels and channel models: a) U. Koert, Chem. Unserer Zeit 1997, 31, 20; b) G. W. Gokel, O. Murillo, Acc. Chem. Res. 1996, 29, 425; c) T. M. Fyles, W. F. van Straaten-Nijenhuis, in Comprehensive Supramoleculur Chemistry, Vol. 10 (Ed.: D. N. Reinhouldt), Elsevier, Oxford, 1996, p. 53; d) N. Voyer, Top. Curr. Chem. 1996, 184, 1; some more recent references: e) S. Otto, M. Osifchin, S. L. Regen, J. Am. Chem. Soc. 1999, 121, 10440; f) Z. Qi, M. Sokabe, K. Donowaki, H. Ishida, Biophys. J. 1999, 76, 631; g) E. Abel, E. M. Maguire, O. Murillo, I. Suzuki, S. L. DeWall, G. W. Gokel, J. Am. Chem. Soc. 1999, 121, 9043; h) M. G. Fritz, P. Walde, D. Seebach, Macromolecules 1999, 32, 574; i) J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, G. W. Gokel, Angew. Chem. 1998, 110, 1650; Angew. Chem. Int. Ed. 1998, 37, 1534.
42. Reviews on nonpeptide ion channels and channel models: a) U. Koert, Chem. Unserer Zeit 1997, 31, 20; b) G. W. Gokel, O. Murillo, Acc. Chem. Res. 1996, 29, 425; c) T. M. Fyles, W. F. van Straaten-Nijenhuis, in Comprehensive Supramoleculur Chemistry, Vol. 10 (Ed.: D. N. Reinhouldt), Elsevier, Oxford, 1996, p. 53; d) N. Voyer, Top. Curr. Chem. 1996, 184, 1; some more recent references: e) S. Otto, M. Osifchin, S. L. Regen, J. Am. Chem. Soc. 1999, 121, 10440; f) Z. Qi, M. Sokabe, K. Donowaki, H. Ishida, Biophys. J. 1999, 76, 631; g) E. Abel, E. M. Maguire, O. Murillo, I. Suzuki, S. L. DeWall, G. W. Gokel, J. Am. Chem. Soc. 1999, 121, 9043; h) M. G. Fritz, P. Walde, D. Seebach, Macromolecules 1999, 32, 574; i) J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, G. W. Gokel, Angew. Chem. 1998, 110, 1650; Angew. Chem. Int. Ed. 1998, 37, 1534.
43. Reviews on nonpeptide ion channels and channel models: a) U. Koert, Chem. Unserer Zeit 1997, 31, 20; b) G. W. Gokel, O. Murillo, Acc. Chem. Res. 1996, 29, 425; c) T. M. Fyles, W. F. van Straaten-Nijenhuis, in Comprehensive Supramoleculur Chemistry, Vol. 10 (Ed.: D. N. Reinhouldt), Elsevier, Oxford, 1996, p. 53; d) N. Voyer, Top. Curr. Chem. 1996, 184, 1; some more recent references: e) S. Otto, M. Osifchin, S. L. Regen, J. Am. Chem. Soc. 1999, 121, 10440; f) Z. Qi, M. Sokabe, K. Donowaki, H. Ishida, Biophys. J. 1999, 76, 631; g) E. Abel, E. M. Maguire, O. Murillo, I. Suzuki, S. L. DeWall, G. W. Gokel, J. Am. Chem. Soc. 1999, 121, 9043; h) M. G. Fritz, P. Walde, D. Seebach, Macromolecules 1999, 32, 574; i) J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, G. W. Gokel, Angew. Chem. 1998, 110, 1650; Angew. Chem. Int. Ed. 1998, 37, 1534.
44. Reviews on nonpeptide ion channels and channel models: a) U. Koert, Chem. Unserer Zeit 1997, 31, 20; b) G. W. Gokel, O. Murillo, Acc. Chem. Res. 1996, 29, 425; c) T. M. Fyles, W. F. van Straaten-Nijenhuis, in Comprehensive Supramoleculur Chemistry, Vol. 10 (Ed.: D. N. Reinhouldt), Elsevier, Oxford, 1996, p. 53; d) N. Voyer, Top. Curr. Chem. 1996, 184, 1; some more recent references: e) S. Otto, M. Osifchin, S. L. Regen, J. Am. Chem. Soc. 1999, 121, 10440; f) Z. Qi, M. Sokabe, K. Donowaki, H. Ishida, Biophys. J. 1999, 76, 631; g) E. Abel, E. M. Maguire, O. Murillo, I. Suzuki, S. L. DeWall, G. W. Gokel, J. Am. Chem. Soc. 1999, 121, 9043; h) M. G. Fritz, P. Walde, D. Seebach, Macromolecules 1999, 32, 574; i) J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, G. W. Gokel, Angew. Chem. 1998, 110, 1650; Angew. Chem. Int. Ed. 1998, 37, 1534.
45. Reviews on nonpeptide ion channels and channel models: a) U. Koert, Chem. Unserer Zeit 1997, 31, 20; b) G. W. Gokel, O. Murillo, Acc. Chem. Res. 1996, 29, 425; c) T. M. Fyles, W. F. van Straaten-Nijenhuis, in Comprehensive Supramoleculur Chemistry, Vol. 10 (Ed.: D. N. Reinhouldt), Elsevier, Oxford, 1996, p. 53; d) N. Voyer, Top. Curr. Chem. 1996, 184, 1; some more recent references: e) S. Otto, M. Osifchin, S. L. Regen, J. Am. Chem. Soc. 1999, 121, 10440; f) Z. Qi, M. Sokabe, K. Donowaki, H. Ishida, Biophys. J. 1999, 76, 631; g) E. Abel, E. M. Maguire, O. Murillo, I. Suzuki, S. L. DeWall, G. W. Gokel, J. Am. Chem. Soc. 1999, 121, 9043; h) M. G. Fritz, P. Walde, D. Seebach, Macromolecules 1999, 32, 574; i) J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, G. W. Gokel, Angew. Chem. 1998, 110, 1650; Angew. Chem. Int. Ed. 1998, 37, 1534.
46. Reviews on nonpeptide ion channels and channel models: a) U. Koert, Chem. Unserer Zeit 1997, 31, 20; b) G. W. Gokel, O. Murillo, Acc. Chem. Res. 1996, 29, 425; c) T. M. Fyles, W. F. van Straaten-Nijenhuis, in Comprehensive Supramoleculur Chemistry, Vol. 10 (Ed.: D. N. Reinhouldt), Elsevier, Oxford, 1996, p. 53; d) N. Voyer, Top. Curr. Chem. 1996, 184, 1; some more recent references: e) S. Otto, M. Osifchin, S. L. Regen, J. Am. Chem. Soc. 1999, 121, 10440; f) Z. Qi, M. Sokabe, K. Donowaki, H. Ishida, Biophys. J. 1999, 76, 631; g) E. Abel, E. M. Maguire, O. Murillo, I. Suzuki, S. L. DeWall, G. W. Gokel, J. Am. Chem. Soc. 1999, 121, 9043; h) M. G. Fritz, P. Walde, D. Seebach, Macromolecules 1999, 32, 574; i) J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, G. W. Gokel, Angew. Chem. 1998, 110, 1650; Angew. Chem. Int. Ed. 1998, 37, 1534.
47. Reviews on nonpeptide ion channels and channel models: a) U. Koert, Chem. Unserer Zeit 1997, 31, 20; b) G. W. Gokel, O. Murillo, Acc. Chem. Res. 1996, 29, 425; c) T. M. Fyles, W. F. van Straaten-Nijenhuis, in Comprehensive Supramoleculur Chemistry, Vol. 10 (Ed.: D. N. Reinhouldt), Elsevier, Oxford, 1996, p. 53; d) N. Voyer, Top. Curr. Chem. 1996, 184, 1; some more recent references: e) S. Otto, M. Osifchin, S. L. Regen, J. Am. Chem. Soc. 1999, 121, 10440; f) Z. Qi, M. Sokabe, K. Donowaki, H. Ishida, Biophys. J. 1999, 76, 631; g) E. Abel, E. M. Maguire, O. Murillo, I. Suzuki, S. L. DeWall, G. W. Gokel, J. Am. Chem. Soc. 1999, 121, 9043; h) M. G. Fritz, P. Walde, D. Seebach, Macromolecules 1999, 32, 574; i) J. de Mendoza, F. Cuevas, P. Prados, E. S. Meadows, G. W. Gokel, Angew. Chem. 1998, 110, 1650; Angew. Chem. Int. Ed. 1998, 37, 1534.
48. T. M. Fyles, D. Loock, X. Zhou, J. Am. Chem. Soc. 1998, 120, 2997.
49. T. M. Fyles, D. Loock, W. F. van Straaten-Nijenhuis, X. Zhou, J. Org. Chem. 1996, 61, 8866.
50. a) N. Voyer, L. Potvin, E. Rousseau, J. Chem. Soc. Perkin Trans. 2 1997, 1469;
51. b) J.-C. Meillon, N. Voyer, Angew. Chem. 1997, 109, 1004; Angew. Chem. Int. Ed. Engl. 1997, 36, 967.
52. b) J.-C. Meillon, N. Voyer, Angew. Chem. 1997, 109, 1004; Angew. Chem. Int. Ed. Engl. 1997, 36, 967.
53. The alternative route to intramolecular ion-conduction pathways (i.e., covalent assembly of all α-helices of an active parallel bundle 8c by a unifying template) was realized earlier: a) M. Mutter, K.-H. Altmann, G. Tuchscherer, Tetrahedron 1988, 44, 771; b) A. Grove, M. Mutter, J. E. Rivier, M. Montal, J. Am. Chem. Soc. 1993, 115, 5919; for template-assembled α-helix bundles with model α-helices similar to 14, see : K. S. Åkerfeldt, R. M. Kim, D. Camac, J. T. Groves, J. D. Lear, W. F. DeGrado, J. Am. Chem. Soc. 1992, 114, 9656; for recent progress in the field of template-assembled α-helix bundles, see: A. R. Mezo, J. C. Sherman, J. Am. Chem. Soc. 1999, 121, 8983; this productive approach is not discussed in the context of this article because is seems incompatible with facile variability of electrostatic asymmetry of nanorods.
54. The alternative route to intramolecular ion-conduction pathways (i.e., covalent assembly of all α-helices of an active parallel bundle 8c by a unifying template) was realized earlier: a) M. Mutter, K.-H. Altmann, G. Tuchscherer, Tetrahedron 1988, 44, 771; b) A. Grove, M. Mutter, J. E. Rivier, M. Montal, J. Am. Chem. Soc. 1993, 115, 5919; for template-assembled α-helix bundles with model α-helices similar to 14, see : K. S. Åkerfeldt, R. M. Kim, D. Camac, J. T. Groves, J. D. Lear, W. F. DeGrado, J. Am. Chem. Soc. 1992, 114, 9656; for recent progress in the field of template-assembled α-helix bundles, see: A. R. Mezo, J. C. Sherman, J. Am. Chem. Soc. 1999, 121, 8983; this productive approach is not discussed in the context of this article because is seems incompatible with facile variability of electrostatic asymmetry of nanorods.
55. The alternative route to intramolecular ion-conduction pathways (i.e., covalent assembly of all α-helices of an active parallel bundle 8c by a unifying template) was realized earlier: a) M. Mutter, K.-H. Altmann, G. Tuchscherer, Tetrahedron 1988, 44, 771; b) A. Grove, M. Mutter, J. E. Rivier, M. Montal, J. Am. Chem. Soc. 1993, 115, 5919; for template-assembled α-helix bundles with model α-helices similar to 14, see : K. S. Åkerfeldt, R. M. Kim, D. Camac, J. T. Groves, J. D. Lear, W. F. DeGrado, J. Am. Chem. Soc. 1992, 114, 9656; for recent progress in the field of template-assembled α-helix bundles, see: A. R. Mezo, J. C. Sherman, J. Am. Chem. Soc. 1999, 121, 8983; this productive approach is not discussed in the context of this article because is seems incompatible with facile variability of electrostatic asymmetry of nanorods.
56. The alternative route to intramolecular ion-conduction pathways (i.e., covalent assembly of all α-helices of an active parallel bundle 8c by a unifying template) was realized earlier: a) M. Mutter, K.-H. Altmann, G. Tuchscherer, Tetrahedron 1988, 44, 771; b) A. Grove, M. Mutter, J. E. Rivier, M. Montal, J. Am. Chem. Soc. 1993, 115, 5919; for template-assembled α-helix bundles with model α-helices similar to 14, see : K. S. Åkerfeldt, R. M. Kim, D. Camac, J. T. Groves, J. D. Lear, W. F. DeGrado, J. Am. Chem. Soc. 1992, 114, 9656; for recent progress in the field of template-assembled α-helix bundles, see: A. R. Mezo, J. C. Sherman, J. Am. Chem. Soc. 1999, 121, 8983; this productive approach is not discussed in the context of this article because is seems incompatible with facile variability of electrostatic asymmetry of nanorods.
57. J.-Y. Winum, S. Matile, J. Am. Chem. Soc. 1999, 121, 7961.
58. F. Robert, J.-Y. Winum, N. Sakai, D. Gerard, S. Matile, Org. Lett. 2000, 2, 37.
59. A new approach to redox-active, centrosymmetric artificial channels has been proposed very recently: C. D. Hall, G. J. Kirkovits, A. C. Hall, Chem. Commun. 1999, 1897; for possible conformational changes of α-helical rods caused by redox-switches, see: H. L. Schenck, G. P. Dado, S. H. Gellman, J. Am. Chem. Soc. 1996, 118, 12487.
60. A new approach to redox-active, centrosymmetric artificial channels has been proposed very recently: C. D. Hall, G. J. Kirkovits, A. C. Hall, Chem. Commun. 1999, 1897; for possible conformational changes of α-helical rods caused by redox-switches, see: H. L. Schenck, G. P. Dado, S. H. Gellman, J. Am. Chem. Soc. 1996, 118, 12487.
61. Y. Hamuro, J. P. Schneider, W. F. DeGrado, J. Am. Chem. Soc. 1999, 121, 12200.
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