Copper(II) Macrocycles Cleave Single-Stranded and Double-Stranded DNA under Both Aerobic and Anaerobic Conditions

Inorganic Chemistry

Volumn 35, Issue 26, 1996, Pages 7474-7481

  Hegg, Eric L ^a   Burstyn, Judith N ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001534259     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic960384n     Document Type: Article

References (96)

1. Radzicka, A.; Wolfenden, R. Science 1995, 267, 90-93.
2. Westheimer, F. H. Science 1987, 235, 1173-1178.
3. (a) Dixon, W. J.; Hayes, J. J.; Levin, J. R.; Weidner, M. F.; Dombroski, B. A.; Tullius, T. D. Methods Enzymol. 1991, 208, 380-403.
4. (b) Pogozelski, W. K.; McNeese, T. J.; Tullius, T. D. J. Am. Chem. Soc. 1995, 117, 6428-6433.
5. (a) Chen, X.; Burrows, C. J.; Rokita, S. E. J. Am. Chem. Soc. 1992, 114, 322-325.
6. (b) Burrows, C. J.; Rokita, S. E. Acc. Chem. Res. 1994, 27, 295-301.
7. Price, M. A.; Tullius, T. D. Methods Enzymol. 1992, 212, 194-219.
8. (a) Pope, L. E.; Sigman, D. S. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 3-7.
9. (b) Sigman, D. S. Biochemistry 1990, 29, 9097-9105.
10. (a) Stubbe, J.; Kozarich, J. W. Chem. Rev. 1987, 87, 1107-1136.
11. (b) Cohen, S. S. In Bleomycin: Chemical, Biochemical, and Biological Aspects; Hecht, S. M., Ed.; Springer-Verlag: New York, 1979; pp 267-286.
12. (a) Hertzberg, R. P.; Dervan, P. B. J. Am. Chem. Soc. 1982, 104, 313-315.
13. (b) Hertzberg, R. P.; Dervan, P. B. Biochemistry 1984, 23, 3934-3945.
14. (c) Dervan, P. B. Methods Enzymol. 1991, 208, 497-515.
15. (a) Lempers, E. L. M.; Bashkin, J. S.; Kostić, N. M. Nucleic Acids Res. 1993, 21, 1983-1990.
16. (b) Iverson, B. L.; Shreder, K.; Morishima, T.; Rosingana, M.; Sessler, J. L. J. Org. Chem. 1995, 60, 6616-6620.
17. (a) Rabow, L. E.; McGall, G. H.; Stubbe, J.; Kozarich, J. W. J. Am. Chem. Soc. 1990, 112, 3203-3208.
18. (b) Worth, L., Jr.; Frank, B. L.; Christter, D. F.; Absalon, M. J.; Stubbe, J.; Kozarich, J. W. Biochemistry 1993, 32, 2601-2609.
19. (c) Absalon, M. J.; Wu, W.; Kozarich, J. W.; Stubbe, J. Biochemistry 1995, 34, 2076-2086.
20. (a) Hecht, S. M. Acc. Chem. Res. 1986, 19, 383-391.
21. (b) Van Atta, R. B.; Long, E. C.; Hecht, S. M.; van der Marel, G. A.; van Boom, J. H. J. Am. Chem. Soc. 1989, 111, 2722-2724.
22. (a) Sigman, D. S.; Graham, D. R.; D'Aurora, V.; Stern, A. M. J. Biol. Chem. 1979, 254, 12269-12272.
23. (b) Sigman, D. S.; Kuwabara, M. D.; Chen, C. H. B.; Bruice, T. W. Methods Enzymol. 1991, 208, 414-433.
24. (c) Pan, C. Q.; Landgraf, R.; Sigman, D. S. Mol. Microbiol. 1994, 12, 335-342.
25. De Rosch, M. A.; Trogler, W. C. Inorg. Chem. 1990, 29, 2409-2416.
26. (a) Hashimoto, S.; Yamashita, R.; Nakamura, Y. Chem. Lett. 1992, 1639-1542.
27. (b) Hashimoto, S.; Nakamura, Y. J. Chem. Soc., Chem. Commun. 1995, 1413-1414.
28. (a) Joshi, R. R.; Likhite, S. M.; Kumar, R. K.; Ganesh, K. N. Biochim. Biophys. Acta 1994, 1199, 285-292.
29. (b) Joshi, R. R.; Ganesh, K. N. Proc. Indian Acad. Sci. (Chem. Sci.) 1994, 106, 1089-1108.
30. (a) Shullenberger, D. F.; Long, E. C. Bioorg. Med. Chem. Lett. 1993, 3, 333-336.
31. (b) Shullenberger, D. F.; Eason, P. D.; Long, E. C. J. Am. Chem. Soc. 1993, 115, 11038-11039.
32. (a) Ranganathan, D.; Mishra, R. K.; Patel, B. K.; Vaish, N. K. Proc. Indian Acad. Sci. (Chem. Sci.) 1994, 106, 1071-1088.
33. (a) Morrow, J. R.; Kolasa, K. A. Inorg. Chim. Acta 1992, 195, 245-248.
34. (b) Mack, D. P.; Dervan, P. B. J. Am. Chem. Soc. 1990, 112, 4604-4606.
35. (c) Mack, D. P.; Dervan, P. B. Biochemistry 1992, 31, 9399-9405.
36. (a) Chen, X.; Rokita, S. E.; Burrows, C. J. J. Am. Chem. Soc. 1991, 113, 5884-5886.
37. (b) Muller, J. G.; Chen, X.; Dadiz, A. C.; Rokita, S. E.; Burrows, C. J. J. Am. Chem. Soc. 1992, 114, 6407-6411.
38. (a) Le Doan, T.; Perrouault, L.; Helene, C.; Chassignol, M.; Thuong, N. T. Biochemistry 1986, 25, 6736-6739.
39. (b) Groves, J. T.; Marla, S. S. J. Am. Chem. Soc. 1995, 117, 9578-9579.
40. (c) Ward, B.; Skorobogaty, A.; Dabrowiak, J. C. Biochemistry 1986, 25, 6875-6883.
41. (a) Nielsen, P. E.; Jeppesen, C.; Buchardt, O. FEBS Lett. 1988, 235, 122-124.
42. (b) Nielsen, P. E.; Møllegaard, N. E.; Jeppesen, C. Nucl. Acids Res. 1990, 18, 3847-3851.
43. (c) Nielsen, P. E.; Hiort, C.; Sönnichsen, S. H.; Buchardt, O.; Dahl, O.; Nordèn, B. J. Am. Chem. Soc. 1992, 114, 4967-4975.
44. Kalsbeck, W. A.; Grover, N.; Thorp, H. H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1517-1518.
45. (a) Sitlani, A.; Long, E. C.; Pyle, A. M.; Barton, J. K. J. Am. Chem. Soc. 1992, 114, 2303-2312.
46. (b) Chow, C. S.; Barton, J. K. Methods Enzymol. 1992, 212, 219-242.
47. Barton, J. K.; Raphael, A. L. J. Am. Chem. Soc. 1984, 106, 2466-2468.
48. (a) Grover, N.; Gupta, N.; Singh, P.; Thorp, H. H. Inorg. Chem. 1992, 31, 2014-2020.
49. (b) Neyhart, G. A.; Grover, N.; Smith, S. R.; Kalsbeck, W. A.; Fairley, T. A.; Cory, M.; Thorp, H. H. J. Am. Chem. Soc. 1993, 115, 4423-4428.
50. (c) Cheng, C. C.; Goll, J. G.; Neyhart, G. A.; Welch, T. W.; Singh, P.; Thorp, H. H. J. Am. Chem. Soc. 1995, 117, 2970-2980.
51. Johnston, D. H.; Cheng, C. C.; Campbell, K. J.; Thorp, H. H. Inorg. Chem. 1994, 33, 6388-6390.
52. (a) Chin, J.; Zou, X. J. Am. Chem. Soc. 1988, 110, 223-225.
53. (b) Kim, J. H.; Chin, J. J. Am. Chem. Soc. 1992, 114, 9792-9795.
54. Hendry, P.; Sargeson, A. M. Inorg. Chem. 1990, 29, 92-97.
55. Hendry, P.; Sargeson, A. M. J. Am. Chem. Soc. 1989, 111, 2521-2527.
56. (a) Breslow, R.; Zhang, B. J. Am. Chem. Soc. 1994, 116, 7893-7894.
57. (b) Takeda, N.; Irisawa, M.; Komiyama, M. J. Chem. Soc., Chem. Commun. 1994, 2773-2774.
58. (c) Schneider, H. J.; Rammo, J.; Hettich, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1716-1719.
59. (d) Takasaki, B. K.; Chin, J. J. Am. Chem. Soc. 1995, 117, 8582-8585.
60. (a) Hay, R. W.; Govan, N. J. Chem. Soc., Chem. Commun. 1990, 714-715.
61. (b) Oh, S. J.; Song, K. H.; Park, J. W. J. Chem. Soc., Chem. Commun. 1995, 575-576.
62. Scandium, Yttrium & the Lanthanides: Inorganic & Coordination Chemistry; King, R. B., Ed.; Encyclopedia of Inorganic Chemistry; John Wiley & Sons: New York, 1994; Vol. 7, Chapter 3.
63. (a) Fenton, D. E.; Vigato, P. A. Chem. Soc. Rev. 1988, 17, 69-90.
64. (b) Morrow, J. R.; Buttrey, L. A.; Shelton, V. M.; Berback, K. A. J. Am. Chem. Soc. 1992, 114, 1903-1905.
65. (c) Amin, S.; Morrow, J. R.; Lake, C. H.; Churchill, M. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 773-775.
66. (a) Young, M. J.; Wahnon, D.; Hynes, R. C.; Chin, J. J. Am. Chem. Soc. 1995, 117, 9441-9447.
67. (b) Morrow, J. R.; Trogler, W. C. Inorg. Chem. 1988, 27, 3387-3394.
68. (c) Kövári, E.; Heitker, J.; Krämer, R. J. Chem. Soc., Chem. Commun. 1995, 1205-1206.
69. (a) Burstyn, J. N.; Deal, K. A. Inorg. Chem. 1993, 32, 3585-3586.
70. (b) Deal, K. A.; Burstyn, J. N. Inorg. Chem. 1996, 35, 2792-2798.
71. (c) Deal, K. A.; Hengge, A. C.; Burstyn, J. N. J. Am. Chem. Soc. 1996, 118, 1713-1718.
72. (a) Browne, K. A.; Bruice, T. C. J. Am. Chem. Soc. 1992, 114, 4951-4958.
73. (b) Koike, T.; Kimura, E. J. Am. Chem. Soc. 1991, 113, 8935-8941.
74. (c) Hikichi, S.; Tanaka, M.; Moro-oka, Y.; Kitajima, N. J. Chem. Soc., Chem. Commun. 1992, 814-815.
75. Kesicki, E. A.; DeRosch, M. A.; Freeman, L. H.; Wallon, C. L.; Harvey, D. F.; Trogler, W. C. Inorg. Chem. 1993, 32, 5851-5867.
76. Chapman, W. H., Jr.; Breslow, R. J. Am. Chem. Soc. 1995, 117, 5462-5469.
77. Wahnon, D.; Lebuis, A. M.; Chin, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2412-2414.
78. Basile, L. A.; Raphael, A. L.; Barton, J. K. J. Am. Chem. Soc. 1987, 109, 7550-7551.
79. (a) Rammo, J.; Hettich, R.; Roigk, A.; Schneider, H. J. J. Chem. Soc., Chem. Commun. 1996, 105-107.
80. (b) Takasaki, B. K.; Chin, J. J. Am. Chem. Soc. 1994, 116, 1121-1122.
81. (a) Komiyama, M.; Shiiba, T.; Kodama, T.; Takeda, N.; Sumaoka, J.; Yashiro, M. Chem. Lett. 1994, 1025-1028.
82. (b) Komiyama, M.; Takeda, N.; Shiiba, T.; Takahashi, Y.; Matsumoto, Y.; Yashiro, M. Nucleosides Nucleotides 1994, 13, 1297-1309.
83. (c) Komiyama, M.; Takeda, N.; Takahashi, Y.; Uchida, H.; Shiiba, T.; Kodama, T.; Yashiro, M. J. Chem. Soc., Perkin Trans. 2 1995, 269-274.
84. Schnaith, L. M. T.; Hanson, R. S.; Que, L., Jr. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 569-573.
85. Hegg, E. L.; Burstyn, J. N. J. Am. Chem. Soc. 1995, 117, 7015-7016.
86. Halfen, J. A.; Mahapatra, S.; Wilkinson, E. C.; Gengenbach, A. J.; Young, V. G., Jr.; Que, Jr., L.; Tolman, W. B. J. Am. Chem. Soc. 1996, 118, 763-776.
87. Sambrook, J.; Fritsch, E. F.; Maniatis, T. In Molecular Cloning: A Laboratory Manual, 2nd ed.; Ford, N., Ed.; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 1989.
88. (a) 0.5 × TBE buffer is 22.5 mM Tris - borate and 0.5 mM EDTA. (b) 1 × TAE buffer is 40 mM Tris - acetate and 1.0 mM EDTA.
89. Haidle, C. W.; Lloyd, R. S.; Robberson, D. L. In Bleomycin: Chemical, Biochemical, and Biological Aspects; Hecht, S. M., Ed.; Springer-Verlag: New York, 1979; pp 222-243.
90. (a) Basile, L. A.; Barton, J. K. J. Am. Chem. Soc. 1987, 109, 7548-7550.
91. (b) Kishikawa, H.; Xiang, Y. P.; Goodisman, J.; Dabrowiak, J. C. J. Am.Chem. Soc. 1991, 113, 5434-5440.
92. Hegg, E. L.; Mortimore, S. H.; Cheung, C. L.; Huyett, J. E.; Burstyn, J. N. University of Wisconsin-Madison, manuscript in preparation.
93. 2 from the reaction mixtures.
94. Halfen, J. A.; Schneider, J. L.; Tolman, W. B. University of Minnesota, unpublished results.
95. 45
96. Sigman, D. S.; Mazumder, A.; Perrin, D. M. Chem. Rev. 1993, 93, 2295-2316.