Design and synthesis of a stable supramolecular trigonal prism formed by the self-assembly of a linear tetrakis(zn2+-cyclen) complex and trianionic trithiocyanuric acid in aqueous solution and its complexation with dna (cyclen = 1,4,7,10-tetraazacyclododecane)

Inorganic Chemistry

Volumn 48, Issue 19, 2009, Pages 9567-9578

  Zulkefeli, Mond ^a,b   Sogon, Tetsuya ^c   Takeda, Kei ^c   Kimura, Eiichi ^c   Aoki, Shin ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b UNIVERSITI TEKNOLOGI MARA   (Malaysia)

^c HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,4,7,10 TETRAAZACYCLODODECANE; DNA; HETEROCYCLIC COMPOUND; TRIAZINE DERIVATIVE; TRITHIOCYANURIC ACID;

ARTICLE; CHEMISTRY; KINETICS; SOLUTION AND SOLUBILITY;

DNA; HETEROCYCLIC COMPOUNDS; KINETICS; SOLUTIONS; TRIAZINES;

EID: 70349765778     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic901407d     Document Type: Article

References (133)

1. (a) Coon, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647-1668.
2. (b) Caulder, D. L.; Raymond, K. N. J. Chem. Soc., Dalton Trans. 1999, 1185-1200.
3. (c) Ward, M. D.; McCleverty, J. A.; Jeffery, J. C. Coord. Chem. Rev. 2001, 222, 251-272.
4. (d) Sun, W.-Y.; Yoshizawa, M.; Kasukawa, T.; Fujita, M. Curr. Opin. Chem. Biol. 2002, 6, 757-764.
5. (e) Park, K.-M.; Whang, D.; Lee, E.; Heo, J.; Kim, K. Chem-Eur. J. 2002, 8, 498-508.
6. (f) Fujita, M; Tominaga, M; Hori, A.; Therrien, B. Ace Chem. Res. 2005, 38, 371-380.
7. (g) Friedler, D.; Leung, D. H.; Bergman, R. G.; Raymond, K. N. Ace Chem. Res. 2005, 38, 349-358.
8. (h) Lützen, A. Angew. Chem., Int. Ed. 2005, 44, 1000-1002.
9. (i) Pluth, M; Raymond, K. N. Chem. Soc. Rev. 2007, 36, 161-171.
10. (j) Kumar, A.; Sun, S.-S.; Lees, A. J. Coord. Chem. Rev. 2008, 252, 922-939.
11. (a) Amabilino, D. B.; Ashton, P. R.; Balzani, V.; Brown, C. L.; Credi, A.; Frchet, J. M. L.; Leon, J. W.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; Venturi, M. J. Am. Chem. Soc. 1996, 118, 12012-12020.
12. (b) Ryan, D.; Rao, S. N.; Rensmo, H.; Fitmaurice, D.; Preeoe, J. A.; Wenger, S.; Stoddart, J. F.; Zaooheroni, N. J. Am. Chem. Soc. 2000, 122, 6252-6257.
13. (c) Raymo, F. M.; Bartberger, M. D.; Honk, K. N.; Stoddart, J. F. J. Am. Chem. Soc. 2001, 123, 9264-9267.
14. (d) Hernandez, R.; Tseng, H.-R.; Wong, J. W.; Stoddart, J. F.; Zink, J. I. J. Am. Chem. Soc. 2004, 126, 3370-3371.
15. (e) Park, J.; Lang, K.; Abboud, K. A.; Houg, S. J. Am. Chem. Soc. 2008, 130, 16484-16485.
16. (a) Balaban, T. S.; Goddard, R.; Linke-Schaetzel, M.; Lehn, J.-M. J. Am. Chem. Soc. 2003, 125, 4233-4239.
17. (b) Barboiu, M.; Vaughan, G.; Graff, R; Lehn, J.-M. J. Am. Chem. Soc. 2003, 125, 10257-10265.
18. (c) Ruben, M.; Rojo, J.; Romeo-Salguero, F. J.; Uppadine, L. H.; Lehn, J.-M. Angew. Chem., Int. Ed. 2004, 43, 3644-3662.
19. (d) Ramirez, J.; Stadler, A.-M.; Rogez, G.; Drillon, M.; Lehn, J.-M. Inorg. Chem. 2009, 48, 2456-2463.
20. (a) Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Angew. Chem., Int. Ed. 2001, 40, 2382-2426.
21. (b) Atwood, J. L.; Leonard, J. B.; Agoston, J. Science 2002, 296, 2367-2369.
22. (c) Kubik, S.; Rebeller, C.; Stüwe, S. J. Incl. Phenom. Macrocycl. Chem. 2005, 52, 137-187.
23. (d) Schmuck, C. Angew. Chem., Int. Ed. 2007, 46, 5830-5833.
24. (e) Oshovsky, G. V.; Reinhoudt, D. N.; Verboom, W. Angew. Chem., Int. Ed. 2007, 46, 2366-2393.
25. (a) Fujita, M. Molecular Self-Assembly Organic Versus Inorganic Approaches; Springer: Berlin, 2000; Vol. 96.
26. (b) Fujita, M.; Umemoto, K.; Yoshizawa, M.; Fujita, N.; Kusukawa, T.; Biradha, K. J. Chem. Soc., Chem. Commun. 2001, 509-518.
27. (c) Kusukawa, T.; Fujita, M. J. Am. Chem. Soc. 2002, 124, 13576-13582.
28. (d) Nakabayashi, K.; Kawano, M.; Yoshizawa, M.; Ohkoshi, S.-I.; Fujita, M. J. Am. Chem. Soc. 2004, 126, 16694-16695.
29. (e) Yoshizawa, M.; Fujita, M. Pure. Appl. Chem. 2005, 77, 1107-1112.
30. (f) Fujita, M.; Tominaga, M.; Hori, A.; Themen, B. Acc. Chem. Res. 2005, 38, 371-380.
31. (g) Kawano, M.; Kobayashi, Y.; Ozeki, T.; Fujita, M. J. Am. Chem. Soc. 2006, 128, 6558-6559.
32. (h) Maurizot, V.; Yoshizawa, M.; Kawano, M.; Fujita, M. Dalton Trans. 2006, 2750-2756.
33. (i) Suzuki, K.; Kawano, M.; Sato, S.; Fujita, M. J. Am. Chem. Soc. 2007, 129, 10652-10653.
34. (j) Yamauohi, Y.; Yoshizawa, M.; Fujita, M. J. Am. Chem. Soc. 2008, 130, 5832-5833.
35. (a) Caulder, D. L.; Raymond, K. N. Acc. Chem. Res. 1999, 32, 975982.
36. (b) Brumaghim, J. L.; Martin, M.; Raymond, K. N. Eur. J. Org. Chem. 2004, 24, 4552-4559.
37. (c) Seeber, G.; Tiedemann, B. E. F.; Raymond, K. N. Top. Curr. Chem. 2006, 265, 147-183.
38. (d) Fiedler, D.; Halbeek, H. V.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2006, 128, 10240-10252.
39. (e) Biros, S. M.; Bergman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 12094-12095.
40. (a) Linton, B.; Hamilton, A. D. Chem. Rev. 1997, 97, 1669-1680.
41. (b) Babině, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1359-1472.
42. (c) Davis, J. M.; Tsou, L. K.; Hamilton, A. D. Chem. Soc. Rev. 2007, 36, 326-334.
43. (d) Sawada, T.; Yoshizawa, M.; Sato, S.; Fujita, M. Nature Chem. 2009, 1, 53-56.
44. (a) Meistermann, I.; Moreno, V.; Prieto, M. J.; Moldrheim, E.; Sletten, E.; Khalid, S.; Rodger, P. M.; Peberdy, J. C.; Isaac, C. J.; Rodger, A.; Hannon, M. J. Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 5069-5074.
45. (b) Oleksi, A.; Blanco, A. G.; Boer, R.; Uso'n, I.; Aymami, J.; Rodger, A.; Hannon, M. J.; Coll, M. Angew. Chem., Int. Ed. 2006, 45, 1227-1231.
46. (c) Cerasimo, L.; Hannon, M. J.; Sletten, E. Inorg. Chem. 2007, 46, 6245-6251.
47. Hannon, M. J. Chem. Soc. Rev. 2007, 36, 280-295.
48. (a) Vallée, B. L.; AuId, D. S. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 220-224.
49. (b) Christiansen, D. W. Adv. Prot. Chem. 1991, 42, 281-335.
50. (c) Coleman, J. E. Annu. Rev. Biochem. 1992, 61, 897-946.
51. (a) Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry: A Comprehensive Text, 5th ed., Vol 1; John Wiley & Sons: New York, 1988.
52. (b) Arnold, F. H.; Haymore, B. L. Science 1991, 252, 1796-1797.
53. (c) Vallée, B. L.; Falohuk, K. H. Phys. Rev. 1993, 73, 79-118.
54. (d) Vallée, B. L.; Auld, D. S Ace Chem. Rev 1993, 26, 543-551.
55. (e) Christiansen, D. W.; Cox, J. D. Annu. Rev. Biochem. 1999, 68, 33-57.
56. (f) Auld, D. S. Biometals 2001, 14, 271-313.
57. (a) Kimura, E.; Koike, T. In Comprehensive Supramolecular Chemistry; Reinhoudt, D. N., Ed.; Pergamon: Tokyo, 1996; Vol. 10, pp 429-444.
58. (b) Koike, T.; Watanabe, T.; Aoki, S.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 12696-12703.
59. (c) Kimura, E. S. Aft. J. Chem. 1997, 50, 240-248.
60. (d) Kimura, E.; Koike, T.; Shionoya, M. In Structure and Bonding: Metal Site in Proteins and Models; Sadler, J. P., Ed.; Springer: Berlin, 1997; Vol. 89, pp 1 -28.
61. (e) Kimura, E.; Koike, T. Chem. Soc. Rev. 1998, 27, 179-184.
62. (f) Kimura, E.; Koike, T. In Bioinorganic Catalysis; Reedijk, J., Bouwman, E., Eds.; Marcel Dekkar, Ino: New York, 1999; pp 33-54.
63. (g) Kimura, E.; Kikuta, E. J. Biol. Inorg. Chem. 2000, 5, 139-155.
64. (h) Kimura, E. Curr. Opin. Chem. Biol. 2000, 4, 207-213.
65. (i)Kimura, E. Ace Chem. Res. 2001, 34, 171-179.
66. (j) Kimura, E.; Aoki, S. BioMetals 2001, 14, 191-204.
67. (k) Aoki, S.; Kimura, E. Rev. Mol. Biotech. 2002,90,129-155.
68. (l) Aoki, S.; Kimura, E. Chem. Rev. 2004, 104, 769-787.
69. (m) Kimura, E.; Takasawa, R.; Tanuma, S.; Aoki, S. Science STKE 2004,17.
70. Kimura, E.; Ikeda, T.; Shionoya, M.; Shiro, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 663-664.
71. (a) Kimura, E.; Shiota, T.; Koike, T.; Shiro, M.; Kodama, M. J. Am. Chem. Soc. 1990, 112, 5805-5811.
72. (b) Koike, T.; Kimura, E.; Nakamura, I.; Hashimoto, Y.; Shiro, M. J. Am. Chem. Soc. 1992, 114, 7338-7345.
73. (c) Zhang, X.; van Eldik, R.; Koike, T.; Kimura, E. Inorg. Chem. 1993, 32, 5749-5755.
74. (d) Fujioka, H.; Koike, T.; Yamada, N.; Kimura, E. Heterocycles 1996, 42, 775-787.
75. (e) Kimura, E.; Aoki, S.; Koike, T.; Shiro, M. J. Am. Chem. Soc. 1997, 119, 3068-3076.
76. (f ) Aoki, S.; Kimura, E. J. Am. Chem. Soc. 2000, 122, 4542-4548.
77. (g) Aoki, S.; Iwaida, K.; Hanamoto, N.; Shiro, M.; Kimura, E. J. Am. Chem. Soc. 2002, 124, 5256-5257.
78. (a) Shionoya, M.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1993,115, 6730-6737.
79. (b) Shionoya, M.; Ikeda, T.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 3848-3859.
80. (c) Koike, T.; Takashige, M.; Kimura, E.; Fujioka, H.; Shiro, M. Chem.-Eur. J. 1996, 2, 617-623.
81. (d) Kimura, E.; Ikeda, T.; Aoki, S.; Shionoya, M. J. Biol. Inorg. Chem. 1998, 3, 259-267.
82. (e) Aoki, S.; Honda, Y.; Kimura, E. J. Am. Chem. Soc. 1998, 120, 10018-10026.
83. (f) Aoki, S.; Sugimura, C.; Kimura, E. J. Am. Chem. Soc. 1998, 120, 10094-10102.
84. (g) Kikuta, E.; Murata, M.; Katsube, N.; Koike, T.; Kimura, E. J. Am. Chem. Soc. 1999, 121, 5426-5436.
85. (h) Kimura, E.; Kikuta, E. Prog. React. Kinet. Mech. 2000, 25, 164.
86. (i) Kimura, E.; Kitamura, H.; Ohtani, K.; Koike, T. J. Am. Chem. Soc. 2000, 122, 4668-4677.
87. (j) Kikuta, E.; Aoki, S.; Kimura, E. J. Am. Chem. Soc. 2001, 123, 7911-7912.
88. (k) Kikuta, E.; Aoki, S.; Kimura, E. J. Biol. Inorg. Chem. 2002, 7, 473-482.
89. (l) Kimura, E.; Katsube, N.; Koike, T.; Shiro, M.; Aoki, S. Supramol. Chem. 2002, 14, 95-102.
90. (m) Gasser, G.; Belousoff, M. J.; Bond, A. M.; Kosowski, Z.; Spiocia, L. Inorg. Chem. 2007, 46, 1665-1674.
91. Aoki, S.; Kagata, D.; Shiro, M.; Takeda, K.; Kimura, E. J. Am. Chem. Soc. 2004, 126, 13377-13390.
92. (a) For reviews of anion receptors and sensors, see: (a) Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; VCH: Weinheim, Germany, 1995.
93. (b) Supramolecular Chemistry of Anions; Bianohi, A., Bowman-James, K., Garoia-Espana, E., Eds.; Wiley-VCH: New York, 1996.
94. (c) Sessler, J. L.; Andrievsky, A.; Genge, J. W. In Advances in Supramolecular Chemistry; Gokel, G. W., Ed.; JAI Press Inc.: Greenwich, CT, 1997; Vol. 4, pp 97-142.
95. (d) de Silva, A. P.; Nimal Gunaratne, H. Q.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566.
96. (e) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
97. (f) Beer, P. D. Ace Chem. Res. 1998, 31, 71-80.
98. (g) Beer, P. D.; Cadman, J. Coord. Chem. Rev. 2000, 205, 131-155.
99. (h) Anzenbaoher, P., Jr; Try, A. C.; Miyaji, H.; Jursazí ková, K.; Lynch, V. M.; Marquez, M.; Sessler, J. L. J. Am. Chem. Soc. 2000, 122, 10268-10272.
100. (i) Amendola, V.; Basteianello, E.; Fabbrizzi, L.; Mangano, C.; Pallavioini, P.; Perotti, A.; Lanfredi, A. M.; Ugozzoli, F. Angew. Chem., Int. Ed. 2000, 39, 2917-2920.
101. (j) Peozuh, M. W.; Hamilton, A. D. Chem. Rev. 2000, 100, 2479-2494.
102. (k) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 487-516.
103. (l) Wiskur, S. L.; Ait-Haddou, H.; Anslyn, E. V.; Lavigne, J. J. Ace Chem. Res. 2001, 34, 963-972.
104. (m) Choi, K.; Hamilton, A. D. J. Am. Chem. Soc. 2001, 123, 2456-2457.
105. (n) Rekharsky, M.; Inoue, Y.; Tobey, S.; Metzger, A.; Anslyn, E. J. Am. Chem. Soc. 2002, 124, 14959-14967.
106. (o) Tobey, S. L.; Anslyn, E. V J. Am. Chem. Soc. 2003, 125, 14807-14815.
107. (p) Sakamoto, T.; Ojida, A.; Hamachi, I. Chem. Commun. 2009, 125, 141-152.
108. (q) Wada, A.; Tamara, S.; Ikeda, M.; Hamachi, I. J. Am. Chem. Soc. 2009, 131, 5321-5330.
109. (a) Aoki, S.; Shiro, M.; Koike, T.; Kimura, E. J. Am. Chem. Soc. 2000, 122, 576-584.
110. (b) Aoki, S.; Shiro, M.;Kimura, E. Chem.-Eur. J. 2002, 8, 929-939.
111. Aoki, S.; Zulkefeli, M.; Shiro, M.; Kimura, E. Proc Natl. Acad. Sci. U. S A. 2002, 99, 4894-4899.
112. As suggested by the reviewer, we mention the positive charges of the supramolecular complexes by using the fences "{ }" in this manuscript, because brackets "[ ]" are normally used to represent the concentrations of compounds including their cationic or anionic species.
113. Kimura, E.; Kikuchi, M.; Kitamura, H.; Koike, T. Chem.-Eur. J. 1999, 5, 3113-3123.
114. Dumont, A.; Jacques, V.; Desreux, J. F. Tetrahedron Lett. 1994, 35, 3707-3710.
115. Martell, A. E.; Motekaitis, R. J. Determination and Use of Stability Constants, 2nd ed.; VCH: New York, 1992.
116. The addition of dithiothretol (DTT) and succinimide induced the extensive dissociation of 7 (Figure S1 and S2 in the Supporting Information).
117. (a) LePec, J. B.; Paoletti, C. J. Mol. Biol. 1967, 27, 87-106.
118. (b) Liu, G. D.; Liao, J. P.; Fang, Y. Z.; Huang, S. S.; Shen, G. L.; Yu, R Q. Anal. Sci. 2002, 18, 391-395.
119. (c) Vardevanyan, P. O.; Antonyan, A. P.; Parsadanyan, M. A.; Davtyan, H. G.; Karapetyan, A. T. Exp. Mol. Med. 2003, 35, 527-533.
120. Edwards, K. J.; Jenkins, T. C.; Neidle, S. Biochemistry 1992, 31, 7104-7109.
121. (a) Morgan, A. R.; Lee, J. S.; Pulleyblank, D. E.; Murray, N. L.; Evans, D. H. Nucleic Acids Res. 1979, 7, 547-569.
122. (b) Antony, T.; Thomas, T.; Shirahata, A.; Thomas, T. J. Biochemistry 1999, 38, 10775-10784.
123. (c) Blagbrough, I. S.; Adjimatera, N., Ahmed, O. A. A.; Neal, A. P.; Pourzand, C. Neurotox '03: Neurotoxicological Targets from Functional Genomics and Proteomics; Beadle, D. J., Mellor, I. R., Usherwood, P. N. R., Eds.; Society of Chemical Industry: New York, 2004; Chapter 16.
124. Garbet, N. H.; Hammond, N. B.; Graves, D. E. Biophys. J. 2004, 87, 3974-3981.
125. Špačková, N.; Cheatham, T. E.; Ryjáč ek, F.; Lankaš, F.; van Meerveit, L.; Hobza, P.; Šponer, J. J. Am. Chem. Soc. 2003, 125, 1759-1769.
126. Shiraishi, T.; Hamzavi, R.; Nielsen, P. E. Nucleic Acids Res. 2008, 36, 4424-11432
127. Finsy, R. Colloid Interface Sci. 1994, 52, 79-143.
128. Vijayanathan, V.; Thomas, T.; Shirahata, A.; Thomas, T. J. Biochemistry 2001, 40, 13644-13651.
129. Similar behaviors were observed for ctDNA upon the addition of EB, pentamidine, spermine, and 7 (Figure S3 in the Supporting Information).
130. Our preliminary experiments have indicated that 7 induces considerable red shifts in circular dichroism (CD) spectra of ctDNA, while pentamidine and spermine induced small changes in CD spectra of ctDNA (Figure S4 in the Supporting Information). The detail has been examined.
131. Trotta, E.; D'Ambrosio, E.; Del Grosso, N.; Ravagnan, G.; Cirilli, M.; Paci, M. J. Biol. Chem. 1993, 268, 3944-3951.
132. Firth, W. J.; Watkins, C. L.; Graves, D. E.; Yielding, L. W. J. Heterocycl. Chem. 1983, 20, 759-765.
133. Wells, R. D.; Larson, J. E.; Grant, R. C.; Shortle, B. E.; Cantor, C. R. J. Mol. Biol. 1970, 54, 465-1197