Toward artificial ion channels: A lipophilic G-quadruplex

Journal of the American Chemical Society

Volumn 122, Issue 17, 2000, Pages 4060-4067

  Forman, Scott L ^a   Fettinger, James C ^a   Pieraccini, Silvia ^b   Gottarelli, Giovanni ^b   Davis, Jeffery T ^a  

^a UNIVERSITY OF MARYLAND   (United States)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CESIUM ION; GUANOSINE DERIVATIVE; ION CHANNEL; POTASSIUM ION; SILANE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CRYSTALLIZATION; GEOMETRY; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 0034600297     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9925148     Document Type: Article

References (95)

1. (a) Bechinger, B. J. Membr. Biol. 1997, 156, 197-211.
2. (b) Woolley, G. A.; Wallace, B. A. J. Membr. Biol. 1992, 129, 109-136.
3. (a) Akerfeldt, K. S.; Lear, J. D.; Wasserman, Z. R.; Chung, L. A.; DeGrado, W. F. Acc. Chem. Res. 1993, 26, 191-197.
4. (b) Bryson, J. W.; Betz, S. P.; Lu H. S.; Suich, D. J.; Zhou, H. X. X.; O'Neil, K. T.; DeGrado, W. F. Science 1995, 270, 935-941
5. (c) Lear, J. D.; Schneider, J. P.; Kienker, P. K.; DeGrado, W. F. J. Am. Chem. Soc. 1997, 119, 3212-3217.
6. (a) Ghadiri, M. R.; Granja, J. R.; Milligan, R. A.; McRee, D. E. Nature 1993, 366, 324-327.
7. (b) Ghadiri, M. R.; Granja, J. R.; Buehler, L. K. Nature 1994, 369, 301-304.
8. (c) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50.
9. (d) Ranganathan, D.; Haridas, V.; Gilardi, R.; Karle, I. L. J. Am. Chem. Soc. 1998, 120, 10793-10890.
10. (e) Ranganathan, D.; Lakshmi, C.; Karle, I. L. J. Am. Chem. Soc. 1999, 121, 6103-6107.
11. For reviews on artificial ion channels: (a) Gokel, G. W.; Murillo, O. Acc. Chem. Res. 1996, 29, 425-432. (b) Kobuke, Y. In Advances in Supramolecular Chemistry; Gokel, G. W., Ed.; JAI Press: Greenwich, CT, 1997; Vol. 4, pp 163-210.
12. For reviews on artificial ion channels: (a) Gokel, G. W.; Murillo, O. Acc. Chem. Res. 1996, 29, 425-432. (b) Kobuke, Y. In Advances in Supramolecular Chemistry; Gokel, G. W., Ed.; JAI Press: Greenwich, CT, 1997; Vol. 4, pp 163-210.
13. (a) Kobuke, Y.; Ueda, K.; Sokabe, M. J. Am. Chem. Soc. 1992, 114, 7618-7622.
14. (b) Tanaka, Y.; Kobuke, Y.; Sokabe, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 693-694.
15. Menger, F. M.; Aikens, P. Angew. Chem., Int. Ed. Engl. 1992, 31, 898-900.
16. (a) Pregel, M. J.; Jullien, L.; Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1992, 31, 1637-1640.
17. (b) Pregel, M. J.; Jullien, L.; Canceill, J.; Lehn, J.-M. J. Chem. Soc., Perkin Trans. 2 1995, 417-426.
18. (a) Abel, E.; Maguire, G. E. M.; Meadows, E. S.; Murillo, O.; Jin, T.; Gokel, G. W. J. Am. Chem. Soc. 1997, 119, 9061-9062.
19. (b) Murillo, O.; Suzuki, I.; Abel, E.; Murray, C. L.; Meadows, E. S.; Jin, T.; Gokel, G. W. J. Am. Chem. Soc. 1997, 119, 5540-5549.
20. (c) Abel, E.; Maguire, G. E. M.; Murillo, O.; Gokel, G. W. J. Am. Chem. Soc. 1999, 121, 9043-9052.
21. (a) Stadler, E.; Dedek, P.; Yamashita, K.; Regen, S. L. J. Am. Chem. Soc. 1994, 116, 6677-6682.
22. (b) Deng, G.; Dewa, T.; Regen, S. L. J. Am. Chem. Soc. 1996, 118, 8975-8976.
23. (c) Merritt, M.; Lanier, M.; Deng, G.; Regen, S. L. J. Am. Chem. Soc. 1998, 120, 8494-8501.
24. (d) Otto, S.; Osifchin, M.; Regen, S. L. J. Am. Chem. Soc. 1999, 121, 7276-7277.
25. (a) Fyles, T. M.; James, T. D.; Kaye, K. C. J. Am. Chem. Soc. 1993, 115, 12315-12321.
26. (b) Fyles, T. M.; Loock, D.; vanStraaten Nijenhuis, W. F.; Zhou, X. J. Org. Chem. 1996, 61, 8866-8874.
27. (c) Fyles, T. M.; Loock, D.; Zhou, X. J. Am. Chem. Soc. 1998, 120, 2997-3003.
28. (a) Ni, C. Y.; Matile, S. J. Chem. Soc., Chem. Commun. 1998, 755-756.
29. (b) Sakai, N.; Majumdar, N.; Matile, S. J. Am. Chem. Soc. 1999, 121, 4294-4295.
30. (c) Winum, J. Y.; Matile, S. J. Am. Chem. Soc. 1999, 121, 7961-7962.
31. (a) Voyer, N.; Robitaille, M. J. Am. Chem. Soc. 1995, 117, 6599-6600.
32. (b) Meillon, J. C.; Voyer, N. Angew. Chem., Int. Ed. Engl. 1997, 36, 967-969.
33. For the original suggestion: Chen, L.; Sakai, N.; Moshiri, S. T.; Matile S. Tetrahedron Lett. 1998, 39, 3627-3630.
34. For the first fiber X-ray study: Gellert, M.; Lipsett, M. N.; Davies, D. R. Proc. Natl. Acad. Sci. U.S.A. 1962, 48, 2013-2018.
35. For a review on G-quartets from mononucleotides: Guschlbauer, W.; Chantot, J. F.; Thiele, D. J. Biomol. Struct Dynam. 1990, 8, 491-511.
36. Pinnavaia, T. J.; Marshall, C. L.; Mettler, C. M.; Fisk, C. L.; Miles, H. T.; Becker, E. D. J. Am. Chem. Soc. 1978, 97, 3625-3627.
37. (a) Pinnavaia, T. J.; Miles, H. T.; Becker, E. D. J. Am. Chem. Soc. 1975, 97, 7198-7200.
38. (b) Detellier, C.; Laszlo, P. J. Am. Chem. Soc. 1980, 102, 1135-1141.
39. Zimmerman, S. B. J. Mol. Biol. 1976, 106, 663-673.
40. Mariani, P.; Mazabard, C.; Garbesi, A.; Spada, G. P. J. Am. Chem. Soc. 1989, 111, 6369-6373.
41. Zimmerman, S. B.; Cohen, G. H.; Davies, D. R. J. Mol. Biol. 1975, 92, 101.
42. For reviews on oligonucleotide G-quartets: (a) Gilbert, D. E.; Feigon, J. Curr. Opin. Struct. Biol. 1999, 9, 305-314. (b) Williamson, J. R. Annu. Rev. Biophys. Biomol. Struct. 1994, 23, 703-730.
43. For reviews on oligonucleotide G-quartets: (a) Gilbert, D. E.; Feigon, J. Curr. Opin. Struct. Biol. 1999, 9, 305-314. (b) Williamson, J. R. Annu. Rev. Biophys. Biomol. Struct. 1994, 23, 703-730.
44. Leading examples of G-quadruplex NMR structures include: (a) Smith, F. W.; Feigon, J. Nature 1992, 356, 164-168. (b) Wang, Y.; Patel, D. J. Biochemistry 1992, 31, 8112-8119. (c) Cheong, C. J.; Moore, P. B. Biochemists 1992, 31, 8406-8414. (d) Aboul-ela, F.; Murchie, A. I. H.; Norman, D. G.; Lilley, D. M. J. J. Mol. Biol. 1994, 243, 458-471.
45. Leading examples of G-quadruplex NMR structures include: (a) Smith, F. W.; Feigon, J. Nature 1992, 356, 164-168. (b) Wang, Y.; Patel, D. J. Biochemistry 1992, 31, 8112-8119. (c) Cheong, C. J.; Moore, P. B. Biochemists 1992, 31, 8406-8414. (d) Aboul-ela, F.; Murchie, A. I. H.; Norman, D. G.; Lilley, D. M. J. J. Mol. Biol. 1994, 243, 458-471.
46. Leading examples of G-quadruplex NMR structures include: (a) Smith, F. W.; Feigon, J. Nature 1992, 356, 164-168. (b) Wang, Y.; Patel, D. J. Biochemistry 1992, 31, 8112-8119. (c) Cheong, C. J.; Moore, P. B. Biochemists 1992, 31, 8406-8414. (d) Aboul-ela, F.; Murchie, A. I. H.; Norman, D. G.; Lilley, D. M. J. J. Mol. Biol. 1994, 243, 458-471.
47. Leading examples of G-quadruplex NMR structures include: (a) Smith, F. W.; Feigon, J. Nature 1992, 356, 164-168. (b) Wang, Y.; Patel, D. J. Biochemistry 1992, 31, 8112-8119. (c) Cheong, C. J.; Moore, P. B. Biochemists 1992, 31, 8406-8414. (d) Aboul-ela, F.; Murchie, A. I. H.; Norman, D. G.; Lilley, D. M. J. J. Mol. Biol. 1994, 243, 458-471.
48. Kang, C.; Zhang, X.; Ratliff, R.; Moyzis, R.; Rich, A. Nature 1992, 356, 126-131.
49. (a) Laughlan, G.; Murchie, A. I. H.; Norman, D. G.; Moore, M. H.; Moody, P. C. E.; Lilley, D. M. J.; Luisi, B. Science 1994, 265, 520-524.
50. (b) Phillips, K.; Dauter, Z.; Murchie, A. I. H.; Lilley, D. M. J.; Luisi, B. J. Mol. Biol. 1997, 273, 171-182.
51. (a) Hud, N. V.; Schultze, P.; Sklenar, V.; Feigon, J. J. Mol. Biol. 1999, 285, 233-243.
52. (b) Hud, N. V.; Schultze, P.; Feigon, J. J. Am. Chem. Soc. 1998, 120, 6403-6404.
53. Marsh, T. C.; Vesenka, J.; Henderson, E. Biochemistry 1994, 33, 10718-10724.
54. Marsh, T. C.; Vesenka, J.; Henderson, E. Nucleic Acids Res. 1995, 23, 696-700.
55. Davis, J. T.; Tirumala, S.; Jenssen, J. R.; Radler, E.; Fabris, D. J. Org. Chem. 1995, 60, 4167-4176.
56. Gottarelli, G.; Masiero, S.; Spada, G. P. J. Chem. Soc., Chem. Commun. 1995, 2555-2557.
57. For related studies on lipophilic nucleosides: (a) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769-2776. (b)Davis, J. T.; Tirumala, S.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (c) Marlow, A. L.; Davis, J. T. Tetrahedron Lett. 1999, 40, 3539-3542. (d) Gottarelli, G.; Mariani, P.; Masiero, S.; Mezzina, E.; Spada, G. P.; Recanatini, M. Helv. Chim. Acta 1998, 81, 2078-2092. (e) Andrisano, V.; Gottarelli, G.; Masiero, S.; Heijne, E. H.; Pieraccini, S.; Spada, G. P. Angew. Chem., Int. Ed. 1999, 38, 2386-2388. (f) Cai, M.; Marlow, A. L.; Fettinger, J. C.; Fabris, D.; Haverlock, T. J.; Moyer, B. A.; Davis, J. T. Angew. Chem., Int. Ed. 2000, in press.
58. For related studies on lipophilic nucleosides: (a) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769-2776. (b)Davis, J. T.; Tirumala, S.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (c) Marlow, A. L.; Davis, J. T. Tetrahedron Lett. 1999, 40, 3539-3542. (d) Gottarelli, G.; Mariani, P.; Masiero, S.; Mezzina, E.; Spada, G. P.; Recanatini, M. Helv. Chim. Acta 1998, 81, 2078-2092. (e) Andrisano, V.; Gottarelli, G.; Masiero, S.; Heijne, E. H.; Pieraccini, S.; Spada, G. P. Angew. Chem., Int. Ed. 1999, 38, 2386-2388. (f) Cai, M.; Marlow, A. L.; Fettinger, J. C.; Fabris, D.; Haverlock, T. J.; Moyer, B. A.; Davis, J. T. Angew. Chem., Int. Ed. 2000, in press.
59. For related studies on lipophilic nucleosides: (a) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769-2776. (b)Davis, J. T.; Tirumala, S.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (c) Marlow, A. L.; Davis, J. T. Tetrahedron Lett. 1999, 40, 3539-3542. (d) Gottarelli, G.; Mariani, P.; Masiero, S.; Mezzina, E.; Spada, G. P.; Recanatini, M. Helv. Chim. Acta 1998, 81, 2078-2092. (e) Andrisano, V.; Gottarelli, G.; Masiero, S.; Heijne, E. H.; Pieraccini, S.; Spada, G. P. Angew. Chem., Int. Ed. 1999, 38, 2386-2388. (f) Cai, M.; Marlow, A. L.; Fettinger, J. C.; Fabris, D.; Haverlock, T. J.; Moyer, B. A.; Davis, J. T. Angew. Chem., Int. Ed. 2000, in press.
60. For related studies on lipophilic nucleosides: (a) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769-2776. (b)Davis, J. T.; Tirumala, S.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (c) Marlow, A. L.; Davis, J. T. Tetrahedron Lett. 1999, 40, 3539-3542. (d) Gottarelli, G.; Mariani, P.; Masiero, S.; Mezzina, E.; Spada, G. P.; Recanatini, M. Helv. Chim. Acta 1998, 81, 2078-2092. (e) Andrisano, V.; Gottarelli, G.; Masiero, S.; Heijne, E. H.; Pieraccini, S.; Spada, G. P. Angew. Chem., Int. Ed. 1999, 38, 2386-2388. (f) Cai, M.; Marlow, A. L.; Fettinger, J. C.; Fabris, D.; Haverlock, T. J.; Moyer, B. A.; Davis, J. T. Angew. Chem., Int. Ed. 2000, in press.
61. For related studies on lipophilic nucleosides: (a) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769-2776. (b)Davis, J. T.; Tirumala, S.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (c) Marlow, A. L.; Davis, J. T. Tetrahedron Lett. 1999, 40, 3539-3542. (d) Gottarelli, G.; Mariani, P.; Masiero, S.; Mezzina, E.; Spada, G. P.; Recanatini, M. Helv. Chim. Acta 1998, 81, 2078-2092. (e) Andrisano, V.; Gottarelli, G.; Masiero, S.; Heijne, E. H.; Pieraccini, S.; Spada, G. P. Angew. Chem., Int. Ed. 1999, 38, 2386-2388. (f) Cai, M.; Marlow, A. L.; Fettinger, J. C.; Fabris, D.; Haverlock, T. J.; Moyer, B. A.; Davis, J. T. Angew. Chem., Int. Ed. 2000, in press.
62. For related studies on lipophilic nucleosides: (a) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769-2776. (b)Davis, J. T.; Tirumala, S.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271-5272. (c) Marlow, A. L.; Davis, J. T. Tetrahedron Lett. 1999, 40, 3539-3542. (d) Gottarelli, G.; Mariani, P.; Masiero, S.; Mezzina, E.; Spada, G. P.; Recanatini, M. Helv. Chim. Acta 1998, 81, 2078-2092. (e) Andrisano, V.; Gottarelli, G.; Masiero, S.; Heijne, E. H.; Pieraccini, S.; Spada, G. P. Angew. Chem., Int. Ed. 1999, 38, 2386-2388. (f) Cai, M.; Marlow, A. L.; Fettinger, J. C.; Fabris, D.; Haverlock, T. J.; Moyer, B. A.; Davis, J. T. Angew. Chem., Int. Ed. 2000, in press.
63. Marlow, A. L.; Mezzina, E.; Spada, G. P.; Masiero, S.; Davis, J. T.; Gottarelli, G. J. Org. Chem. 1999, 64, 5116-5123.
64. 5′-GMP self-associates in DMSO: West, R. T.; Garza, L. A., II; Winchester, W. R.; Walmsley, J. A. Nucleic Acids Res. 1994, 22, 5128-5134.
65. + octamer: either head-to-tail, tail-to-tail, tail-to-head, or head-to-head.
66. Ross, W. S.; Hardin, C. C. J. Am. Chem. Soc. 1994, 116, 6070-6080.
67. Strahan, G. D.; Keniry, M. A.; Shafer, R. D. Biophys. J. 1998, 75, 968-981.
68. Gu, J.; Leczczynski, J.; Banul, M. Chem. Phys. Lett. 1999, 311, 209-214.
69. Śpačková, N.; Berger, I.; Šponer, J. J. Am. Chem. Soc. 1999, 121, 5519-5534.
70. Coplan, M. A.; Fuoss, R. M. J. Phys. Chem. 1964, 68, 1177.
71. + octamer.
72. -, have so far failed to give quality crystals.
73. Sundquist, W. I.; Klug, A. Nature 1989, 342, 825-829.
74. Williamson, J. R.; Raghuraman, M. K.; Cech, T. R. Cell 1989, 59, 871-880.
75. Shannon, R. D. Acta Crystallogr. A 1976, 32, 751-767.
76. Fenton, D. E. In Comprehensive Coordination Chemistry; McCleverty, J. A., Gillard, R. D., Wilkinson, G., Eds.; Pergamon Press: Oxford, 1987; Vol. 3, p 1.
77. Bryan, J. C.; Kavallieratos, K.; Sachelben, R. A. Inorg. Chem. 2000, in press.
78. Hobza, P.; Šponer, J. Chem. Rev. 1999, 99, 3247-3276.
79. 4 4 quartets are disordered. The dioxalane ring in the G4 2 quartet was modeled as a 50:50 mixture of two major conformations.
80. Davies, D. B. Prog. Nucl. Magn. Res. Spectrosc. 1978, 12, 135-225.
81. Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984.
82. For crystallographic and computational investigation of silyl ether basicity: (a) Shambayati, S.; Schreiber, S., L.; Blake, J. F.; Wierschke, S. G.; Jorgensen, W. L. J. Am. Chem. Soc. 1990, 112, 697-703.
83. (b) Blake, J. F.; Jorgensen, W. L. J. Org. Chem. 1991, 56, 6052-6059.
84. For a review on using CD to characterize G self-assembly: Gottarelli, G.; Masiero, S.; Spada, G. P. Enantiomer 1998, 3, 429-438.
85. Mason, S. F. Molecular Optical Activity and the Chiral Discrimination; Cambridge University Press: Cambridge, 1982; Chapter 6.
86. Hatano, M. Induced Circular Dichroism in Biopolymer-Dye Systems; Springer: Berlin, 1986; p 21.
87. (a) Lawrence, D. S.; Jiang, T., Levin, M. Chem. Rev. 1995, 95, 2229-2260;
88. (b) Philip, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154-1196.
89. Saint+ data reduction program. Bruker Analytical X-ray Systems, Madison, Wisconsin, 1998.
90. (a) Blessing, R. H. Acta Crystallogr. 1995, A51, 33-38.
91. (b) Sheldrick, G. M. SADABS, Siemens Area Detector Absorption Correction; Universität Göttingen: Germany, 1996.
92. Sheldrick, G. M. SHELXTL, version 5.03; Siemens Analytical X-ray Instruments Inc.: Madison, Wisconsin, 1994.
93. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473.
94. Sheldrick, G. M. SHELXL-93, Program for the Refinement of Crystal Structures; University of Göttingen: Germany, 1993.
95. Flack, H. D. Acta Crystallogr. 1983, A39, 876-881.