Synthesis, biological evaluation and DNA binding properties of novel bleomycin analogues

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 15, 2003, Pages 2595-2599

  Xu, Zhi Dong ^a   Wang, Min ^a   Xiao, Su Long ^a   Liu, Chun Li ^a   Yang, Ming ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; BLEOMYCIN; BLEOMYCIN DERIVATIVE; DNA; DRUG DERIVATIVE; TETRAZOLIUM; THIAZOLE DERIVATIVE; THIAZOLYL BLUE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; BINDING SITE; CANCER CELL CULTURE; CARBOXY TERMINAL SEQUENCE; DNA BINDING; DNA CLEAVAGE; DRUG EFFECT; DRUG SCREENING; GEL CHROMATOGRAPHY; HELA CELL; HUMAN; HUMAN CELL; HYDROPHOBICITY; IN VITRO STUDY; KINETICS; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; PHYSICAL CHEMISTRY; SYNTHESIS; TUMOR CELL LINE;

EID: 0038492516     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00435-9     Document Type: Article

References (26)

1. Umezawa H., Maeda K., Takeuchi T., Okami Y. J. Antibiot. Ser. A. 19:1966;200.
2. Bleomycin Chemotherapy; Sikic, B. I., Rozencweig, M., Carter, S. K., Eds.; Academic Press: Orlando, FL, 1985.
3. Hecht, S. M. In Cancer Chemotherapeutic Agents; Foye, W. O., Ed.; American Chemical Society: Washington, DC, 1995; p 369.
4. Hecht S.M. ACC. Chem. Rev. 19:1986;383.
5. Kane S.A., Hecht S.M. Prog. Nucleic Acids Res. Mol. Biol. 49:1994;313.
6. Radtke K., Lornitzo F.A., Byrnes R.S., Antholine W.E., Petering D.H. Biochem. J. 302:1994;655.
7. Hecht S.M. J. Nat. Prod. 63:2000;158.
8. Levy M.J., Hecht S.M. Biochemistry. 27:1988;2647.
9. Sucheck S.J., Ellena J.F., Hecht S.M. J. Am. Chem. Soc. 120:1998;7450.
10. Boger D.L., Aquila B.M., Tse W.C., Searcey M. Tetrahedron Lett. 41:2000;9493.
11. Katano K., An H., Aoyagi Y., Overhand M., Sucheck S.J., Stevens W.C. Jr., Hess C.D., Zhou X., Hetch S.M. J. Am. Chem. Soc. 120:1998;11285.
12. Abraham A.T., Zhou X., Hecht S.M. J. Am. Chem. Soc. 123:2001;5167.
13. Umezawa H. Lloydia. 40:1977;67.
14. Berry D.E., Chang L.H., Hecht S.M. Biochemistry. 24:1985;3207.
15. Yang M., Zhu S.M., Liu J., Zhang L.H. J. Chin. Biochem. 11:1995;609.
16. Tanaka W., Takita T. Heterocycles. 13:1979;469.
17. Takahashi K., Ekimoto H., Minamide S., Nishikawa K., Kuramochi H., Motegi A., Nakatani T., Takita T., Takeuchi T., Umezawa H. Cancer Treat. Rev. 14:1987;169.
18. Comis R.L., Kuppinger M.S., Ginsberg S.J., Crooke S.T., Gilbert R., Auchincloss J.H., Prestayko A.W. Cancer Res. 39:1979;5076.
19. Muggia F.M., Louie A.C., Sikic B.I. Cancer Treat. Rev. 10:1983;221.
20. Lehmann T.E., Ming L., Rosen M.E., Que L. Jr. Biochemistry. 36:1997;2807.
21. 1 (5a-f) Demetallation of 4a-f was accomplished by stirring with 15% EDTA (10 mL) at 30°C for 1 h. The reaction mixture was passed through an ion exchange resin (HP-20) column, washed with water successively, and then eluted with acidic methanol MeOH/2 mM HCl (4:1). The eluate was evaporated to remove the solvent and lyophilized to afford 5a-f in 90-95% yield as a white powder.
22. abstract
23. Mosmann T. J. Immunol. Meth. 65:1983;55.
24. 2 was incubation at 25°C. After 30 min, the reaction mixtures were analyzed on a 0.8% agarose gel and visualized by ethidium bromide stain.
25. Ehrenfeld G.M., Murugesan N., Hecht S.M., Chang C., Basus V.J., Oppenheimer N.J. Biochemistry. 24:1985;81.
26. Xu Z.D., Liu H., Wang M., Xiao S.L., Yang M., Bu X.H. J. Inorg. Biochem. 92:2002;149.