Cation-complexation behavior of template-assembled synthetic G-quartets

Journal of Organic Chemistry

Volumn 74, Issue 15, 2009, Pages 5211-5218

  Nikan, Mehran ^a   Sherman, John C ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1H NMR SPECTROSCOPY; CATION SELECTIVITY; DIFFERENT SIZES; G-QUARTET; PULSED-FIELD GRADIENTS; SOLUTION STUDY; VALENCIES;

CESIUM; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITIVE IONS;

CESIUM COMPOUNDS;

CATION; CESIUM; CHLOROFORM; DIMETHYL SULFOXIDE; SODIUM; STRONTIUM;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; DIFFUSION COEFFICIENT; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY;

CATIONS; CESIUM; G-QUADRUPLEXES; MAGNETIC RESONANCE SPECTROSCOPY; PARTICLE SIZE; SODIUM; STRONTIUM;

EID: 68049094101     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9001245     Document Type: Article

References (63)

1. Neidle, S.; Balasubramanian, S. Quadruplex nucleic acids; RSC Pub.: Cambridge, UK, 2006.
2. Davis, J. T. Angew. Chem., Int. Ed. 2004, 43, 668-698.
3. Han, H. Y.; Hurley, L. H. Trends Pharmacol. Sci. 2000, 21, 136-142.
4. Stewart, S. A.; Weinberg, R. A. Semin. Cancer Biol. 2000, 10, 399-406.
5. Bodnar, A. G.; Ouellette, M.; Frolkis, M.; Holt, S. E.; Chiu, C. P.; Morin, G. B.; Harley, C. B.; Shay, J. W.; Lichtsteiner, S.; Wright, W. E. Science 1998, 279, 349-352.
6. Ghosal, G.; Muniyappa, K. Biochem. Biophys. Res. Commun. 2006, 343, 1-7.
7. Kaucher, M. S.; Harrell, W. A.; Davis, J. T. J. Am. Chem. Soc. 2006, 128, 38-39.
8. Arnal-Herault, C.; Pasc, A.; Michau, M.; Cot, D.; Petit, E.; Barboiu, M. Angew. Chem., Int. Ed. 2007, 46, 8409-8413.
9. Pieraccini, S.; Gottarelli, G.; Mariani, P.; Masiero, S.; Saturni, L.; Spada, G. P. Chirality 2001, 13, 7-12.
10. Calzolari, A.; Di Felice, R.; Molinari, E.; Garbesi, A. Appl. Phys. Lett. 2002, 80, 3331-3333.
11. Gellert, M.; Lipsett, M. N.; Davies, D. R. Proc. Natl. Acad. Sci. U.S.A. 1962, 48, 2013-2018.
12. Zimmerman, S. B.; Cohen, G. H.; Davies, D. R. J. Mol. Biol. 1975, 92, 181-192.
13. Tougard, P.; Chantot, J. F.; Guschlbauer, W. Biochim. Biophys. Acta 1973, 308, 9-16.
14. Pinnavaia, T. J.; Marshall, C. L.; Mettler, C. M.; Fisk, C. I.; Miles, H. T.; Becker, E. D. J. Am. Chem. Soc. 1978, 100, 3625-3627.
15. Gu, J.; Leszczynski, J.; Bansal, M. Chem. Phys. Lett. 1999, 311, 209-214.
16. Wlodarczyk, A.; Grzybowski, P.; Patkowski, A.; Dobek, A. J. Phys. Chem. B 2005, 109, 3594-3605.
17. Wong, A.; Wu, G. J. Am. Chem. Soc. 2003, 125, 13895-13905.
18. van Leeuwen, F. W. B.; Davis, J. T.; Verboom, W.; Reinhoudt, D. N. Inorg. Chim. Acta 2006, 359, 1779-1785.
19. 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.
20. Wong, A.; Ida, R.; Wu, G. Biochem. Biophys. Res. Commun. 2005, 337, 363-366.
21. Wong, A.; Fettinger, J. C.; Forman, S. L.; Davis, J. T.; Wu, G. J. Am. Chem. Soc. 2002, 124, 742-743.
22. Deng, H.; Braunlin, W. H. J. Mol. Biol. 1996, 255, 476-483.
23. Ma, L.; Iezzi, M.; Kaucher, M. S.; Lam, Y. F.; Davis, J. T. J. Am. Chem. Soc. 2006, 128, 15269-15277.
24. Sket, P.; Crnugelj, M.; Plavec, J. Nucleic Acids Res. 2005, 33, 3691-3697.
25. Sen, D.; Gilbert, W. Nature 1990, 344, 410-414.
26. Hardin, C. C.; Henderson, E.; Watson, T.; Prosser, J. K. Biochemistry 1991, 30, 4460-4472.
27. Nikan, M.; Sherman, J. C. Angew. Chem., Int. Ed. 2008, 47, 4900-4902.
28. Otero, R.; Schock, M.; Molina, L. M.; Laegsgaard, E.; Stensgaard, I.; Hammer, B.; Besenbacher, F. Angew. Chem., Int. Ed. 2005, 44, 2270-2275.
29. Kotch, F. W.; Sidorov, V.; Lam, Y. F.; Kayser, K. J.; Li, H.; Kaucher, M. S.; Davis, J. T. J. Am. Chem. Soc. 2003, 125, 15140-15150.
30. Sessler, J. L.; Sathiosatham, M.; Doerr, K.; Lynch, V.; Abboud, K. A. Angew. Chem., Int. Ed. 2000, 39, 1300-1303.
31. Kaucher, M. S.; Davis, J. T. Tetrahedron Lett. 2006, 47, 6381-6384.
32. Shannon, R. D.; Prewitt, C. T. Acta Crystallogr., Sect. B: Struct. Sci. 1969, B 25, 925.
33. Forman, S. L.; Fettinger, J. C.; Pieraccini, S.; Gottareli, G.; Davis, J. T. J. Am. Chem. Soc. 2000, 122, 4060-4067.
34. No free species are observed in the NMR spectra of the cation complexes at temperatures where exchange is slow.
35. Marlow, A. L.; Mezzina, E.; Spada, G. P.; Masiero, S.; Davis, J. T.; Gottarelli, G. J. Org. Chem. 1999, 64, 5116-5123.
36. Aboulela, F.; Murchie, A. I. H.; Lilley, D. M. J. Nature 1992, 360, 280-282.
37. Wang, Y.; Patel, D. J. Biochemistry 1992, 31, 8112-8119.
38. Patel, D. J.; Kozlowski, S. A.; Nordheim, A.; Rich, A. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 1413-1417.
39. Feigon, J.; Wang, A. H. J.; Vandermarel, G. A.; Vanboom, J. H.; Rich, A. Nucleic Acids Res. 1984, 12, 1243-1263.
40. Cohen, Y.; Avram, L.; Frish, L. Angew. Chem., Int. Ed. 2005, 44, 520-554.
41. Schalley, C. A. Analytical methods in supramolecular chemistry; Wiley-VCH: Weinheim, Germany, 2007, 163-220.
42. Evan-Salem, T.; Baruch, I.; Avram, L.; Cohen, Y.; Palmer, L. C.; Rebek, J. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 12296-12300.
43. Avram, L.; Cohen, Y. J. Am. Chem. Soc. 2002, 124, 15148-15149.
44. Kaucher, M. S.; Lam, Y. F.; Pieraccini, S.; Gottarelli, G.; Davis, J. T. Chem. - Eur. J. 2004, 11, 164-173.
45. Evan-Salem, T.; Frish, L.; van Leeuwen, F. W. B.; Reinhoudt, D. N.; Verboom, W.; Kaucher, M. S.; Davis, J. T.; Cohen, Y. Chem. - Eur. J. 2007, 13, 1969-1977.
46. Timmerman, P.; Weidmann, J. L.; Jolliffe, K. A.; Prins, L. J.; Reinhoudt, D. N.; Shinkai, S.; Frish, L.; Cohen, Y. J. Chem. Soc., Perkin Trans. 2 2000, 2077-2089.
47. Waldeck, A. R.; Kuchel, P. W.; Lennon, A. J.; Chapman, B. E. Prog. Nucl. Magn. Reson. Spectrosc. 1997, 30, 39-68.
48. Gottarelli, G.; Masiero, S.; Spada, G. P. J. Chem. Soc., Chem. Commun. 1995, 2555-2557.
49. Mezzina, E.; Mariani, P.; Itri, R.; Masiero, S.; Pieraccini, S.; Spada, G. P.; Spinozzi, F.; Davis, J. T.; Gottarelli, G. Chem. - Eur. J. 2001, 7, 388-395.
50. Aggerholm, T.; Nanita, S. C.; Koch, K. J.; Cooks, R. G. J. Mass Spectrom. 2003, 38, 87-97.
51. Talanova, G. G.; Elkarim, N. S. A.; Talanov, V. S.; Hanes, R. E.; Hwang, H. S.; Bartsch, R. A.; Rogers, R. D. J. Am. Chem. Soc. 1999, 121, 11281-11290.
52. Olsher, U.; Feinberg, H.; Frolow, F.; Shoham, G. Pure Appl. Chem. 1996, 68, 1195-1199.
53. Inoue, Y.; Fujiwara, C.; Wada, K.; Tai, A.; Hakushi, T. J. Chem. Soc., Chem. Commun. 1987, 393-394.
54. Bohmer, V.; Dalla Cort, A.; Mandolini, L. J. Org. Chem. 2001, 66, 1900-1902.
55. +. Under the anhydrous conditions reported here, the selectivity observed reflects the intrinsic selectivity. See ref 1 and references cited therein.
56. DeFilippi, I.; Yates, S.; Sedath, R.; Straszewski, M.; Andren, M.; Gaita, R. Sep. Sci. Technol. 1997, 32, 93-113.
57. Hobbs, D. T.; Barnes, M. J.; Pulmano, R. L.; Marshall, K. M.; Edwards, T. B.; Bronikowski, M. G.; Fink, S. D. Sep. Sci. Technol. 2005, 40, 3093-3111.
58. Fasman, G. D. Circular dichroism and the conformational analysis of biomolecules; Plenum Press: New York, 1996.
59. Gottarelli, G.; Masiero, S.; Spada, G. P. Enantiomer 1998, 3, 429-438.
60. In G-quadruplexes, the CD bands similar to those obtained for TASQs have been related to an antiparallel G-quadruplex with alternate syn and anti conformations. Because of the presence of additional chromophores, the shape of the CD bands of TASQs cannot be interpreted as such.
61. Barrett, E. S.; Irwin, J. L.; Picker, K.; Sherburn, M. S. Aust. J. Chem. 2002, 55, 319-325.
62. Ceulemans, G.; Vandendriessche, F.; Rozenski, J.; Herdewijn, P. Nucleosides Nucleotides 1995, 14, 117-127.
63. Wong, K. H.; Ng, H. L. J. Coord. Chem. 1981, 11, 49-55.