Synthesis and DNA binding properties of amide bond-modified analogues related to distamycin

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7801-7804

  Yamamoto, Yasuo ^a   Kimachi, Tetsutaro ^a   Kanaoka, Yoshitomo ^a   Kato, Satoshi ^a   Bessho, Kiyoshi ^a   Matsumoto, Takuyuki ^a   Kusakabe, Tetsuya ^a   Sugiura, Yukio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DISTAMYCIN A DERIVATIVE;

ARTICLE; DNA BINDING; DNA CLEAVAGE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY;

EID: 0030597146     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01782-0     Document Type: Article

References (22)

1. 1. Di Marco, A.; Gaetani, M.; Orezzi, P.; Scotti, T.; Arcamone, F. Cancer Chemother. Rep. 1962, 18, 15.
2. 2. Kopka, M. L.; Yoon, C.; Goodsell, D.; Pijura, P.; Dickerson, R. E. Proc. Natl. Acad. Sci. USA 1985, 82, 1376.
3. 3. Recent references; (a) Hartley, J. A.; Webber, J.; Wyatt, M, D.; Bordenic, N.; Lee, M. Bioorg. & Med. Chem. 1995, 3, 623.
4. (b) Chen, Y.-H.; Lown, J. W. J. Am. Chem. Soc. 1994, 116, 6995.
5. (c) Yamamoto, Y.; Cai, J.; Nakamura, H.; Sadayori, N.; Asao, N.; Nemoto, H. J. Org. Chem. 1995, 60, 3352.
6. (d) Mrksich, M.; Dervan, P. B. J. Am. Chem. Soc. 1995, 117, 3325.
7. 4. (a) Lown, J. W.; Krowicki, K.; Bhat, U. G.; Skorobogaty, A.; Ward, B.; Dabrowiak, J. C. Biochemistry 1986, 25, 7408.
8. (b) Kissinger, K.; Krowicki, K.; Dabrowiak, J. C.; Lown, J. W. Biochemistry 1987, 26, 5590.
9. (c) Lee, M.; Chang, D. K.; Hartley, J. A.; Pon, R. T.; Krowicki, K.; Lown, J. W. Biochemistry 1988, 27, 445.
10. (d) Lee, M.; Chang, D. K.; Hartley, J. A. Biochemistry 1993, 32, 4237.
11. 5. Nishiwaki, E.; Tanaka, S.; Lee, H.; Shibuya, M. Heterocycles 1988, 27, 1945.
12. 6. Taylor, J. S.; Schults, P. G.; Dervan, P. B. Tetrahedron 1984, 40, 457.
13. 7. Special care must be paid to avoid the drastic elevation of reaction temperature when it bacomes higher than -5°C.
14. 8. (a) Frank, W, C.; Kim, Y. C.; Heck, R. F. J. Org. Chem. 1978, 43, 2947.
15. (b) de Meijere, A.; Meyer, F. E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
16. (c) Heck, R. F. Organic Reactions, published by John Wiley & Sons Inc., 1982, 27, 345.
17. 4).
18. 10. (a) Jensen, H. P.; Sharpless, K. B. J. Org. Chem. 1974, 39, 2314.
19. (b) Sharpless, K. B.; Lauer, R. F.; Oljan, R.; Teranishi, A. Y.; Williams, D. R. J. Am. Chem. Soc. 1971, 93, 3303.
20. 6)
21. 12. Morgan, A. R.; Lee, J. S.; Pulleyblank, D. F.; Murray, N. L.; Evans, D. H. Nucl. Acids. Res. 1979, 7, 547. These experiments followed conditions used in ref. 4 (d). Buffer solution (pH = 7.0) containing Tris-HCl (10 mM) and sodium chloride (10mM) was used.
22. 13. A 50 μM MPE-Fe(II) solution was prepared by mixing a 100 μM MPE aqueous solution (20 μL) with a freshly prepared 100 μM ferrous ammonium sulfate aqueous solution (20 μL). Reaction mixture (16 μL) containing each compound, the labeled restriction fragment, sonicated calf thymus DNA (0.4 μg), sodium chloride, and Tris-HCl (pH = 7.5) was incubated at 20 °C for 30 min. To each tube was added 2 μL of a 50 μM MPE-Fe(II) solution followed by 2 μL of 100 mM dithiothreitol. Final concentrations were 5μM [MPE-Fe(II)], 10mM (dithiothreitol), 50 mM (sodium chloride), and 20 mM (Tris-HCl). The solutions were incubated at 20 °C for 10 min, lyophilized and electrophopresed.