Toward Efficient Zn(II)-Based Artificial Nucleases

Journal of the American Chemical Society

Volumn 126, Issue 14, 2004, Pages 4543-4549

  Boseggia, Elisa ^a   Gatos, Maddalena ^b   Lucatello, Lorena ^a   Mancin, Fabrizio ^a   Moro, Stefano ^a   Palumbo, Manlio ^a   Sissi, Claudia ^a   Tecilla, Paolo ^c   Tonellato, Umberto ^a   Zagotto, Giuseppe ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b CNR   (Italy)

^c UNIVERSITY OF TRIESTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; DNA; INTERCALATION COMPOUNDS; SYNTHESIS (CHEMICAL);

HYDROLYTIC CLEAVING AGENTS; PLASMIDS;

ZINC COMPOUNDS;

ALKYL GROUP; ANTHRAQUINONE; CYCLOHEXANE DERIVATIVE; LIGAND; METAL COMPLEX; NUCLEASE; PLASMID DNA; TRIAMINOCYCLOHEXANE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CHEMICAL MODIFICATION; CONJUGATION; DNA CLEAVAGE; HYDROLYSIS; PH; PLASMID; SYNTHESIS;

ANTHRAQUINONES; BIOMIMETIC MATERIALS; CYCLOHEXANES; DEOXYRIBONUCLEASES; INTERCALATING AGENTS; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; PLASMIDS; ZINC;

EID: 11144355697     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039465q     Document Type: Article

References (59)

1. (a) Westheimer F. H. Science 1987, 235, 1173-1178.
2. (b) Williams, N. H.; Takasaki, B.; Wall, M.; Chin. J. Acc. Chem. Res. 1999, 32, 485-493.
3. (a) Sträter, N.; Lipscomb, W. N.; Klabunde, T.; Krebs, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2024-2055.
4. (b) Wilcox, D. E. Chem. Rev. 1996, 96, 2435-2458.
5. (c) Cowan, J. A. Chem. Rev. 1998, 98, 1067-1088.
6. (d) Jedrzejas, M. J.; Setlow, P. Chem. Rev. 2001, 101, 608-618.
7. (a) Blaskó, A.; Bruice, T. C. Acc. Chem. Res. 1999, 32, 475-484.
8. (b) Bashkin. J. K. Curr. Opin. Chem. Biol. 1999, 3, 752-758.
9. Hegg, E. L.; Burstyn, J. N. Coord. Chem. Rev. 1998, 173, 133-165.
10. Selected examples: (a) Rammo, J.; Hettich, R.; Roigk, A.; Schneider, H.-J. Chem. Commun. 1996, 105-107.
11. (b) Hettich, R.; Schneider, H.-J. J. Am. Chem. Soc. 1997, 119. 5638-5647.
12. (c) Dixon. N. E.; Geue, R. J.; Lambert, J. N.; Moghaddas, S.; Pearce, D. A.; Sargeson, A. L. Chem. Commun. 1996, 1287-1288.
13. (d) Schnaith. L. H.; Hanson, R. S.; Que, L., Jr. Proc. Natl. Acad. Sci. U.S.A. 1994, 91. 569-573.
14. (e) Ragunathan, K. G.; Schneider H.-J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1219-1221.
15. (f) Komiyama, M.; Takeda, N.; Shigekawa, H. Chem. Commun. 1999, 1443-1451.
16. (g) Branum, M. E.; Tipton, A. K.; Zhu, S.; Que, L., Jr. J. Am. Chem. Soc. 2001, 123, 1898-1904.
17. (h) Chand, D. K.; Schneider, H.-J.; Bencini, A.; Bianchi, A.; Giorgi, C. ; Ciattini, S.; Valtancoli, B. Chem.-Eur. J. 2000, 6, 4001-4008.
18. (i) Deck, K. M.; Tseng, T. A.; Burstyn, J. N. Inorg. Chem. 2002, 41, 669-677.
19. (j) Ren, R.; Yang, P.; Zheng, W.; Hua, Z. Inorg. Chem. 2000, 39, 5454-5463.
20. (k) Sissi, C.; Mancin, F.; Palumbo. M.; Scrimin, P.; Tecilla, P.; Tonellato, U. Nucleosides, Nucleotides & Nucleic Acids 2000, 19, 1265-1271.
21. (l) Sreedhara, A.; Freed, J. D.; Cowan, J. A. J. Am. Chem. Soc. 2000. 122, 8814-8824.
22. (m) Itoh, T.; Hisada, H.; Sumiya, T.; Hosono. M.; Usui; Y.; Fujii, Y. Chem. Commun. 1997, 677-678.
23. Franklin, S. J. Curr. Opin. Chem. Biol. 2001, 5, 201-208.
24. (a) Basile, L. A.; Raphael, A. L.; Barton, J. K. J. Am. Chem. Soc. 1987. 109, 7550-7551.
25. (b) Aka, F. N.; Akkaya, M. S.; Akkaya, E. U. J. Mol. Catal. A 2001, 165, 291-294.
26. (c) Ichikawa, K.; Tarani, M.; Uddin. M. K.; Nakata, K.; Sato, S. J. Inorg. Biochem. 2002, 91, 437-450.
27. (a) Fitzsimons. M. P.; Barton, J. K. J. Am. Chem. Soc. 1997, 119, 3379.
28. (b) Copeland. K. D.; Fitzsimons, M. P.; Houser, R. P.; Barton, J. K. Biochemistry 2002, 41, 343-356.
29. Sissi. C.; Rossi, P.; Felluga, F.; Formaggio, F.; Palumbo. M.; Tecilla, P.; Toniolo, C.; Scrimin. P. J. Am. Chem. Soc. 2001, 123, 3169-3170.
30. See for example: (a) Erkkila, K. E.; Odom. D. T.; Barton, J. K. Chem. Rev. 1999, 99, 2777-2795.
31. (b) Chen, C.-B.; Milne. L.; Landgraf, R.; Perrin. D. M.; Sigman, D. S. ChemBioChem 2001, 2, 735-740.
32. (a) Hashimoto, S.; Nakamura, Y. J. Chem. Soc., Chem. Commun. 1995, 1413-1414.
33. (b) Hashimoto, S.; Nakamura, Y. J. Chem. Soc., Perkin Trans. 1 1996, 2623-2628.
34. Calculated from refs 51 and 5m.
35. Bonfá, L.; Gatos, M.; Mancin, F.; Tecilla, P.; Tonellato, U. Inorg. Chem. 2003, 42, 3943-3949.
36. (a) Lown. J. W.; Morgan, A. R.; Yen, S. F.; Wang. Y. H.; Wilson, W. D. Biochemistry 1985, 24, 4028-4035.
37. (b) Gatto, B.; Zagotto, G.; Sissi, C.; Cera, C.; Uriarte, E.; Palu, G.; Capranico, G.; Palumbo, M. J. Med. Chem. 1996, 39, 3114-3122.
38. (a) Bowen, T.; Planalp, R. P.; Brechbiel, M. W. Bioorg. Med. Chem. Lett. 1996, 6, 807.
39. (b) Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974. 30, 2151.
40. Bell, R. A.; Faggiani, R.; Hunter, H. N.; Lock, J. L. Can, J. Chem. 1992, 70, 186.
41. Langhals, H.; Saulich, S. Chem.-Eur. J. 2002, 8, 5630
42. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria. G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery. J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tornasi, J.; Barone. V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson. G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick. D. K.; Rabuck. A. D.; Raghavachari. K.; Foresman. J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu. G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts. R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laharn. M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
43. Molecular Operating Environment (MOE version 2002.02). Chemical Computing Group, Inc., 1255 University St., Suite 1600, Montreal, Quebec, Canada, H3B 3X3.
44. NAMOT2 (Nucleic Acid Modeling Tool); Los Alamos National Laboratory: Los Alamos, New Mexico, 1997.
45. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould. I. R.; Merz, K. M.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 5179.
46. Baxter. C. A.; Murray, C. W.; Clark, D. E.; Westhead, D. R.; Eldridge, M. D. Proteins: Struct., Funct., Genet. 1998, 33, 367.
47. (a) Halgren, T. A. J. Comput. Chem. 1996, 17, 490.
48. (b) Halgren, T. A. J. Comput. Chem. 1996, 17, 520.
49. (c) Halgren, T. A. J. Comput. Chem. 1996, 17, 553.
50. (d) Halgren, T. A. J. Comput. Chem. 1996, 17, 587.
51. (e) Halgren, T. A: Nachbar, R. J. Comput. Chem. 1996, 17, 616.
52. (f) Halgren, T. A. J. Comput. Chem. 1999, 20, 72.
53. (g) Halgren, T. A. J. Comput. Chem. 1999. 20, 730.
54. Qiu. D.; Shenkin, S.; Hollinger, F. P.; Still, W. C. J. Phys. Chem. 1997, 101, 3005.
55. Mallams, A. K.; Morton, J. B.; Reichert, P. J. Chem. Soc., Perkin Trans. 1 1981, 2186.
56. Ammann, H.; Dupuis, G. Can. J. Chem. 1988, 66, 1651.
57. Heckendorn, R.; Allgeier, H.; Baud, J.; Gunzenhauser, W.; Angst, C. J. Med. Chem. 1993, 36, 3721.
58. Wei, W.; Tomohiro, T.; Kodaka, M.; Okuno. H. J. Org. Chem. 2000, 65, 8979.
59. Giardina, D.; Brasili, L.; Gregori, M.; Massi, M.; Picchio, M. T.; Quagli, V.; Melchiorre, C. J. Med. Chem. 1989, 32, 50.