Nuclear magnetic resonance and mass spectrometry studies of 2′,3′,5′-O-triacetylguanosine self-assembly in the presence of alkaline earth metal ions (Ca2+, Sr2+, Ba2+)

Canadian Journal of Chemistry

Volumn 89, Issue 7, 2011, Pages 835-844

  Kwan, Irene C M ^a   She, Yi Min ^a   Wu, Gang ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

Alkaline earth metal; G quartet; Guanosine (G); Mass spectrometry; Nuclear magnetic resonance; Self assembly; Structural elucidation

Indexed keywords

ELECTROSPRAY IONIZATION MASS SPECTROMETRY; G-QUARTET; GUANOSINES; OCTAMERS; RELATIVE BINDING AFFINITY; STRUCTURAL DETAILS; STRUCTURAL DETERMINATION; STRUCTURAL ELUCIDATION; TWIST ANGLES;

BARIUM; BINDING ENERGY; BIOMOLECULES; CALCIUM; ELECTROSPRAY IONIZATION; HIGH ENERGY PHYSICS; LIGHT METALS; MASS SPECTROMETRY; METAL IONS; METALS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RESONANCE; SELF ASSEMBLY;

NUCLEAR MAGNETIC RESONANCE;

EID: 80051514374     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v10-179     Document Type: Article

References (60)

1. Gellert M. Lipsett M. N. Davies D. R. Proc. Natl. Acad. Sci. U.S.A. 1962, 48 (12), 2013. 10.1073/pnas.48.12.2013
2. Davis J. T. Angew. Chem. Int. Ed. 2004, 43 (6), 668. 10.1002/anie. 200300589 (Pubitemid 38197045)
3. Davis J. T. Spada G. P. Chem. Soc. Rev. 2007, 36 (2), 296. 10.1039/b600282j
4. Lena S. Masiero S. Pieraccini S. Spada G. P. Chem. Eur. J. 2009, 15 (32), 7792. 10.1002/chem.200802506
5. Sessler J. L. Sathiosatham M. Doerr K. Lynch V. Abboud K. A. Angew. Chem. Int. Ed. 2000, 39 (7), 1300. 10.1002/(SICI)1521-3773(20000403)39:7<1300:: AID-ANIE1300>3.0.CO;2-I
6. 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 (49), 15140. 10.1021/ja0364165 (Pubitemid 37509678)
7. Otero R. Schöck M. Molina L. M. Lægsgaard E. Stensgaard I. Hammer B. Besenbacher F. Angew. Chem. Int. Ed. 2005, 44 (15), 2270. 10.1002/anie.200461586 (Pubitemid 40560901)
8. Phillips K. Dauter Z. Murchie A. I. H. Lilley D. M. J. Luisi B. J. Mol. Biol. 1997, 273 (1), 171. 10.1006/jmbi.1997.1292 (Pubitemid 27460223)
9. Hud, N. V.; Plavec, J. Quadruplex Nucleic Acid; Neidle, S., Balasubramanian, S., Eds.; RSC Publishing: Cambridge, UK, 2006; Chapter 4.
10. Pinnavaia T. J. Marshall C. L. Mettler C. M. Fisk C. L. Miles H. T. Becker E. D. J. Am. Chem. Soc. 1978, 100 (11), 3625. 10.1021/ja00479a070
11. Wong A. Ida R. Spindler L. Wu G. J. Am. Chem. Soc. 2005, 127 (19), 6990. 10.1021/ja042794d (Pubitemid 40676727)
12. Wu G. Kwan I. C. M. J. Am. Chem. Soc. 2009, 131 (9), 3180. 10.1021/ja809258y
13. Walmsley J. A. Burnett J. F. Biochemistry 1999, 38 (42), 14063. 10.1021/bi9900370 (Pubitemid 29504238)
14. Hightower J. B. Olmos D. R. Walmsley J. A. J. Phys. Chem. B 2009, 113 (36), 12214. 10.1021/jp904383y
15. Kankia B. I. Marky L. A. J. Am. Chem. Soc. 2001, 123 (44), 10799. 10.1021/ja010008o (Pubitemid 33041990)
16. Kwan I. C. M. She Y.-M. Wu G. Chem. Commun. (Camb.) 2007, 4286. 10.1039/b710299b (Pubitemid 47598765)
17. Sen D. Gilbert W. Nature 1988, 334 (6180), 364. 10.1038/334364a0
18. Sen D. Gilbert W. Nature 1990, 344 (6265), 410. 10.1038/344410a0 (Pubitemid 20110090)
19. Sen D. Gilbert W. Biochemistry 1992, 31 (1), 65. 10.1021/bi00116a011
20. Balasubramanian S. Neidle S. Curr. Opin. Chem. Biol. 2009, 13 (3), 345. 10.1016/j.cbpa.2009.04.637
21. Hahn W. C. Stewart S. A. Brooks M. W. York S. G. Eaton E. Kurachi A. Beijersbergen R. L. Knoll J. H. M. Meyerson M. Weinberg R. A. Nat. Med. 1999, 5 (10), 1164. 10.1038/13495 (Pubitemid 29474421)
22. Lena S. Masiero S. Pieraccini S. Spada G. P. Mini Rev. Org. Chem. 2008, 5 (4), 262. 10.2174/157019308786242205
23. Zhou Y. F. Morais-Cabral J. H. Kaufman A. MacKinnon R. Nature 2001, 414 (6859), 43. 10.1038/35102009 (Pubitemid 33041616)
24. MacKinnon R. Angew. Chem. Int. Ed. 2004, 43 (33), 4265. 10.1002/anie.200400662 (Pubitemid 39257401)
25. González-Rodríguez D. Janssen P. G. A. Martín- Rapún R. De Cat I. De Feyter S. Schenning A. P. H. J. Meijer E. W. J. Am. Chem. Soc. 2010, 132 (13), 4710. 10.1021/ja908537k
26. Shi X. Fettinger J. C. Davis J. T. J. Am. Chem. Soc. 2001, 123 (27), 6738. 10.1021/ja004330v (Pubitemid 32916485)
27. Mergny J.-L. Hélène C. Nat. Med. 1998, 4 (12), 1366. 10.1038/3949 (Pubitemid 28553455)
28. Alberti P. Bourdoncle A. Saccà B. Lacroix L. Mergny J.-L. Org. Biomol. Chem. 2006, 4 (18), 3383. 10.1039/b605739j (Pubitemid 44319622)
29. Neidle S. Parkinson G. Nat. Rev. Drug Discov. 2002, 1 (5), 383. 10.1038/nrd793
30. Chen Z. Corey D. R. Adv. Cancer Res. 2003, 87, 31. 10.1016/S0065-230X(03) 87294-9
31. Chen F.-M. Biochemistry 1992, 31 (15), 3769. 10.1021/bi00130a006
32. Smirnov I. Shafer R. H. J. Mol. Biol. 2000, 296 (1), 1. 10.1006/jmbi.1999.3441
33. Kotch F. W. Fettinger J. C. Davis J. T. Org. Lett. 2000, 2 (21), 3277. 10.1021/ol0065120
34. Forman S. L. Fettinger J. C. Pieraccini S. Gottarelli G. Davis J. T. J. Am. Chem. Soc. 2000, 122 (17), 4060. 10.1021/ja9925148 (Pubitemid 30304839)
35. Shi X. Mullaugh K. M. Fettinger J. C. Jiang Y. Hofstadler S. A. Davis J. T. J. Am. Chem. Soc. 2003, 125 (36), 10830. 10.1021/ja035267n (Pubitemid 37087540)
36. van Leeuwen F. W. B. Verboom W. Shi X. Davis J. T. Reinhoudt D. N. J. Am. Chem. Soc. 2004, 126 (50), 16575. 10.1021/ja0455650 (Pubitemid 40081959)
37. Lee M. P. H. Parkinson G. N. Hazel P. Neidle S. J. Am. Chem. Soc. 2007, 129 (33), 10106. 10.1021/ja0740869 (Pubitemid 47312948)
38. Pedroso I. M. Duarte L. F. Yanez G. Baker A. M. Fletcher T. M. Biochem. Biophys. Res. Commun. 2007, 358 (1), 298. 10.1016/j.bbrc.2007.04.126 (Pubitemid 46719116)
39. Nikan M. Sherman J. C. J. Org. Chem. 2009, 74 (15), 5211. 10.1021/jo9001245
40. Miyoshi D. Nakao A. Toda T. Sugimoto N. FEBS Lett. 2001, 496 (2-3), 128. 10.1016/S0014-5793(01)02416-4 (Pubitemid 32441812)
41. Kwan I. C. M. Wong A. She Y.-M. Smith M. E. Wu G. Chem. Commun. (Camb.) 2008, 682. 10.1039/b714803h (Pubitemid 351171423)
42. a Andrisano V. Gottarelli G. Masiero S. Heijne E. H. Pieraccini S. Spada G. P. Angew. Chem. 1999, 111 (16), 2543. 10.1002/(SICI)1521-3757(19990816)111: 16<2543::AID-ANGE2543>3.0.CO;2-G
43. b Andrisano V. Gottarelli G. Masiero S. Heijne E. H. Pieraccini S. Spada G. P. Angew. Chem. Int. Ed. 1999, 38 (16), 2386. 10.1002/(SICI)1521- 3773(19990816)38:16<2386::AID-ANIE2386>3.0.CO;2-S
44. Van Geet A. L. Anal. Chem. 1970, 42 (6), 679. 10.1021/ac60288a022
45. West R. T. Garza L. A. II Winchester W. R. Walmsely J. A. Nucleic Acids Res. 1994, 22 (23), 5128. 10.1093/nar/22.23.5128
46. Kaucher M. S. Lam Y.-F. Peraccini S. Gottarelli G. Davis J. T. Chem. Eur. J. 2005, 11 (1), 164. 10.1002/chem.200400782 (Pubitemid 40065632)
47. Enquist P.-A. Nilsson P. Sjöberg P. Larhed M. J. Org. Chem. 2006, 71 (23), 8779. 10.1021/jo061437d (Pubitemid 44721949)
48. Marlow A. L. Mezzina E. Spada G. P. Masiero S. Davis J. T. Gottarelli G. J. Org. Chem. 1999, 64 (14), 5116. 10.1021/jo9901440 (Pubitemid 29323700)
49. Shi X. Fettinger J. C. Davis J. T. Angew. Chem. Int. Ed. 2001, 40 (15), 2827. 10.1002/1521-3773(20010803)40:15<2827::AID-ANIE2827>3.0.CO;2-1
50. Liu X. Kwan I. C. M. Wang S. Wu G. Org. Lett. 2006, 8 (17), 3685. 10.1021/ol061236w (Pubitemid 44378338)
51. Marti? S. Liu X. Wang S. Wu G. Chem. Eur. J. 2008, 14 (4), 1196. 10.1002/chem.200701411 (Pubitemid 351216938)
52. Shannon R. D. Acta Crystallogr. Sect. A 1976, 32 (5), 751. 10.1107/S0567739476001551
53. Neuhaus, D.; Williamson, M. The Nuclear Overhauser Effect in Structural and Conformational Analysis; VCH Publishers: New York, 1989.
54. Davies D. B. Prog. Nucl. Magn. Reson. Spectrosc. 1978, 12 (3), 135. 10.1016/0079-6565(78)80006-5
55. a Phan A. T. J. Biomol. NMR 2000, 16 (2), 175. 10.1023/A:1008355231085 (Pubitemid 30139892)
56. b Phan A. T. J. Magn. Reson. 2001, 153 (2), 223. 10.1006/jmre.2001.2445
57. Smith F. W. Lau F. W. Feigon J. Proc. Natl. Acad. Sci. U.S.A. 1994, 91 (22), 10546. 10.1073/pnas.91.22.10546 (Pubitemid 24329035)
58. Zimmerman S. B. J. Mol. Biol. 1976, 106 (3), 663. 10.1016/0022-2836(76) 90257-6
59. Tougard P. Chantot J.-F. Guschlbauer W. Biochim. Biophys. Acta 1973, 308, 9.
60. Zimmerman S. B. Cohen G. H. Davies D. R. J. Mol. Biol. 1975, 92 (2), 181. 10.1016/0022-2836(75)90222-3