Synthesis and DNA cleavage activity of artificial receptor 1,4,7-triazacyclononane containing guanidinoethyl and hydroxyethyl side arms

Journal of Organic Chemistry

Volumn 72, Issue 5, 2007, Pages 1799-1802

  Sheng, Xin ^a   Lu, Xiao Min ^b   Zhang, Jing Jing ^a   Chen, Yue Ting ^a   Lu, Guo Yuan ^a   Shao, Ying ^a   Liu, Fang ^a   Xu, Qiang ^b  

^a NANJING UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CLEAVAGE EFFICIENCY; ELECTROPHILIC ACTIVATION; MICHAELIS-MENTEN-TYPE EQUATION; PHOSPHODIESTERS;

ESTERS; HYDROXYLATION; KETONES; NITROGEN COMPOUNDS;

DNA;

1 (2 GUANIDINOETHYL) 4 (2 HYDROXYETHYL) 1,4,7 TRIAZACYCLONONANE; CYCLOALKANE; GUANIDINE DERIVATIVE; N (2 HYDROXYETHYL) 1,4,7 TRIAZACYCLONONANE; NONANE; UNCLASSIFIED DRUG; ZINC COMPLEX;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DNA CLEAVAGE; DNA DETERMINATION; DNA STRUCTURE; MICHAELIS MENTEN KINETICS; STRUCTURE ANALYSIS; SYNTHESIS;

DNA FRAGMENTATION; DNA, SUPERHELICAL; GUANIDINE; GUANIDINES; HETEROCYCLIC COMPOUNDS; HYDROGEN-ION CONCENTRATION; KINETICS; NUCLEIC ACID CONFORMATION; PLASMIDS;

EID: 33847616952     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0624041     Document Type: Article

References (67)

1. (a) Liu, C.; Wang, M.; Zhang, T.; Sun, H. Coord. Chem. Rev. 2004, 248, 147-168.
2. (b) Burger, R. M. Chem. Rev. 1998, 98, 1153-1169.
3. (c) Pogozelski, W. K.; Tullius, T. D. Chem. Rev. 1998, 98, 1089-1107.
4. (d) Armitage, B. Chem. Rev. 1998, 98, 1171-1200.
5. (e) Rajski, S. R.; Williams, R. M. Chem. Rev. 1998, 98, 2723-2795.
6. (f) Hegg, E. L.; Burstyn, J. N. Coord. Chem. Rev. 1998, 173, 133-165.
7. (g) Cowan, J. A. Curr. Opin. Chem. Biol. 2001, 5, 634-642.
8. (h) Morrow, J. R.; Iranzo, O. Curr. Opin. Chem. Biol. 2004, 8, 192-200.
9. (i) Chen, C.-A.; Cowan, J. A. Chem. Commun. 2002, 196-197.
10. (j) Perreault, D. M.; Anslyn, E. V. Angew. Chem., Int. Ed. Engl. 1997, 36, 432-450.
11. (a) Erkkila, K. E.; Odom, D. T.; Barton, J. K. Chem. Rev. 1999, 99, 2777-2795.
12. (b) McMillin, D.; McNett, K. M. Chem. Rev. 1998, 98, 1201-1219.
13. (c) Ren, R.; Yang, P.; Zheng, W.; Hua, Z. Inorg. Chem. 2000, 39, 5454-5463.
14. (d) Hurley, A. L.; Mohler, D. L. Org. Lett. 2000, 2, 2745-2748.
15. (e) Branum, M. E.; Tipton, A. K.; Zhu, S.; Que, L., Jr. J. Am. Chem. Soc. 2001, 123, 1898-1904.
16. (f) Komiyama, M.; Kina, S.; Matsumura, K.; Sumaoka, J.; Tobey, S.; Lynch, V. M.; Anslyn, E. J. Am. Chem. Soc. 2002, 124, 13731-13736.
17. (g) Yang, M-Y.; Richard, J. P.; Morrow, J. R. Chem. Commun. 2003, 2832-2833.
18. (h) Park, G.; Tomlinson, J. T.; Melvin, M. S.; Wright, M. W.; Day, C. S.; Manderville, R. A. Org. Lett. 2003, 5, 113-116.
19. (i) Worm, K.; Chu, F.; Matsumoto, K.; Best, M. D.; Lynch, V.; Anslyn, E. V. Chem. Eur. J. 2003, 9, 741-747.
20. (j) Gupta, T.; Dhar, S.; Nethaji, M.; Chakravarty, A. R. Dalton Trans. 2004, 1896-1900.
21. (k) Boseggia, E.; Gatos, M.; Lucatello, L.; Mancin, F.; Moro, S.; Palumbo, M.; Sissi, C.; Tecilla, P.; Tonellato, U.; Zagotto, G. J. Am. Chem. Soc. 2004, 126, 4543-4549.
22. (l) Jin, Y.; Cowan, J. A. J. Am. Chem. Soc. 2005, 127, 8408-8415.
23. (m) Shao, Y.; Zhang, J.; Tu, C.; Dai, C.; Xu, Q.; Guo, Z. J. Inorg. Biochem. 2005, 99, 1490-1496.
24. (n) Feng, G.; Mareque-Rivas, J. C.; Torres, Martin, de Rosales, R.; Williams, N. H. J. Am. Chem. Soc. 2005, 127, 13470-13471.
25. (o) Feng, G.; Mareque-Rivas, J. C.; Williams, N. H. Chem. Commun. 2006, 1845-1847.
26. (p) Li, Q.-L.; Huang, J.; Wang, Q.; Jiang, N.; Xia, C-Q.; Lin, H.-H.; Wu, J.; Yu, X.-Q. Bioorg. Med. Chem. 2006, 14, 4151-4157.
27. (a) Smith, J.; Ariga, K.; Anslyn, E. V. J. Am. Chem. Soc. 1993, 115, 362-364.
28. (b) Morrow, J. R.; Buttrey, L. A.; Shelton, V. M.; Berback, K. A. J. Am. Chem. Soc. 1992, 114, 1903-1905.
29. (c) Franklin, S. J. Curr. Opin. Chem. Biol. 2001, 5, 201-208.
30. (d) Boerner, L. J.; Zaleski, J. M. Curr. Opin. Chem. Biol. 2005, 9, 135-144.
31. (a) Muche, M.-S.; Göbel, M. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 2126-2129.
32. (b) Scheffer, U.; Strick, A.; Ludwig, V.; Peter, S.; Kalden, E.; Göbel. M. W. J. Am. Chem. Soc. 2005, 127, 2211-2217.
33. (c) Gnaccarini, C.; Peter, S.; Scheffer, U.; Vonhoff, S.; Klussmann, S.; Göbel, M. W. J. Am. Chem. Soc. 2006, 128, 8063-8067.
34. (a) Schug, K. A.; Lindner, W. Chem. Rev. 2005, 105, 67-113.
35. (b) Perreault, D. M.; Cabell, L. A.; Anslyn, E. V. Bioorg. Med. Chem. 1997, 5, 1209-1220.
36. (c) Piatek, A. M.; Gray, M.; Anslyn, E. V. J. Am. Chem. Soc. 2004, 126, 9878-9879.
37. (d) Göbel, M. W.; Bats, J. W.; Dürner, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 207-209.
38. (e) Jubian, V.; Veronese, A.; Dixon, R. P.; Hamilton, A. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1237-1239.
39. (f) Linton, B. R.; Goodman, M. S.; Fan, E.; van Arman, S. A.; Hamilton, A. D. J. Org. Chem. 2001, 66, 7313-7319.
40. (g) Oost, T.; Kalesse, M. Tetrahedron 1997, 53, 8421-8438.
41. (h) Kato, T.; Takeuchi, T.; Karube, I. Chem. Commun. 1996, 953-954.
42. (a) Anslyn, E.; Breslow, R. J. Am. Chem. Soc. 1989, 111, 5972-5973.
43. (b) Breslow, R. J. Mol. Catal. 1994, 91, 161-174.
44. Wan, S-H.; Liang, F.; Xiong, X.-Q.; Yang, L.; Wu. X.-J.: Wang, P.; Zhou, X.; Wu, C.-T. Bioorg. Med. Chem. Lett. 2006, 16, 2804-2806.
45. (a) Du, J.-T.; Li, Y.-M.; Wei, W.; Wu, G.-S.; Zhao, Y.-F.; Kanazawa, K.; Nemoto, T.; Nakanishi, H. J. Am. Chem. Soc. 2005, 127, 16350-16351.
46. (b) Feng, Y.; Cao, S.; Xiao, A.; Xie, W.; Li, Y.; Zhao, Y. Peptides 2006, 27, 1554-1560.
47. (a) Cotton, F. A.; Hazen, E. E., Jr.; Legg, M. J. Proc. Nat. Acad. Sci. U.S.A. 1979, 76, 2551-2555.
48. (b) Krämer, R. Coord. Chem. Rev. 1999, 182, 243-261.
49. (a) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
50. (b) Zatar, A.; Melendez, R.; Geib, S. J.; Hamilton, A. D. Terrahedron 2002, 58, 683-690.
51. (c) Schmuck, C.; Geiger, L. J. Am. Chem. Soc. 2004, 126, 8898-8899.
52. (d) Zepik, H. H.; Benner, S. A. J. Org. Chem. 1999, 64, 8080-8083.
53. (e) Liu, F.; Lu, G.-Y.; He, W.-J.; Liu, M.-H.; Zhu, L.-G.; Wu, H.-M. New J. Chem. 2002, 26, 601-606.
54. (a) Kimura, E.; Nakamura, I.; Koike, T.; Shionoya, M.; Kodama, Y.; Ikeda, T.; Shiro, M. J. Am. Chem. Soc 1994, 116, 4764-4771.
55. (b) Kimura, E.; Kodama, Y.; Koike, T.; Shiro, M. J. Am. Chem. Soc. 1995, 117, 8304-8311.
56. (c) Koiket, T.; Kimura, E. J. Am. Chem. Soc. 1991, 113, 8935-8941.
57. Chong, H.-S.; Brechbiel, M. W. Synth. Commun. 2003, 33, 1147-1154.
58. (a) Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. J. Org. Chem. 1992, 57, 2497-2502.
59. (b) Ghosh, A. K.; Hol, W. G. J.; Fan, E. J. Org. Chem. 2001, 66, 2161-2164.
60. (c) Porcheddu, A.; Giacomelli, G.; Chighine, A.; Masala, S. Org. Lett. 2004, 6, 4925-4927.
61. (a) Ordoukhanian, P.; Joyce, G. F. J. Am. Chem. Soc. 2002, 124, 12499-12506.
62. (b) Sreedhara, A.; Freed, J. D.; Cowan, J. A. J. Am. Chem. Soc. 2000, 122, 8814-8824.
63. (c) Flynn-Charlebois, A.; Prior, T. K.; Hoadley, K. A.; Silverman, S. K. J. Am. Chem. Soc. 2003, 125, 5346-5350.
64. Aoki, S.; Iwaida, K.; Hanamoto, N.; Shiro, M.; Kimura, E. J. Am. Chem. Soc. 2002, 124, 5256-5257.
65. (a) Westheimer, F. H. Science 1987, 235, 1173-1178.
66. (b) Sigman, D. S.; Mazumder, A.; Perrin, D. M. Chem. Rev. 1993, 93, 2295-2316.
67. (c) Williams, N. H.; Takasaki, B.; Wall, M.; Chin, J. Acc. Chem. Res. 1999, 32, 485-493.