Bleomycin model complex bearing a carbamoyl derived substituent capable of coordination to the chelated metal ion as a sixth ligand

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 1, 1997, Pages 15-18

  Arai, Takayuki ^a   Shinozuka, Kazuo ^a   Sawai, Hiroaki ^a  

^a GUNMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BLEOMYCIN; BLEOMYCIN DERIVATIVE; COBALT; FERROUS ION; METAL COMPLEX; METAL ION;

ARTICLE; COMPLEX FORMATION; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; IN VITRO STUDY; MODEL; OXIDATION REDUCTION REACTION; PHYSICAL CHEMISTRY;

EID: 0031023674     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00571-9     Document Type: Article

References (26)

1. a) Umezawa, H.; Maeda, K.; Takeuchi, T.; Okami, Y. J. Antibiot. Ser. A , 1966, 19, 200.
2. b) Blum, R. H.; Carter, S. K.; Agre, K. A. Cancer, 1973, 3, 903.
3. a) Sausville, E. A.; Peisach, J.; Horwitz, S. B. Biochem. Biophys. Res. Commun., 1975, 66, 1432.
4. b) Ehrenfeld, G. M.; Shipley, J. B.; Heimbrook, D. C.; Sugiyama, H.; Long, E. C.; van Boom, J. H.; van der Marel, G. A.; Oppenheimer, N. J.; Hecht, S. M. Biochemistry, 1987, 26, 931.
5. a) Sugiura, Y.; Kuwahara, J.; Suzuki, T. FEBS Lett., 1985, 39, 128.
6. b) Kenani, A.; Bailly, C.; Helbecque, N.; Catteau, J. P.; Houssin, R.; Bernier, J. L.; Henichart, J. P. Biochem. J., 1988, 253, 497.
7. a) Takita, T.; Muraoka, Y.; Nakatani, T.; Fujii, A.; Umezawa, H. J. Antibiot., 1978, 31, 1073.
8. b) Oppenheimer, N. J.; Rodriguez, L. O.; Hecht, S. M. Proc. Natl. Acad. Sci. USA, 1979, 76, 11, 5616.
9. a) Oppenheimer, N.; Chang, C.; Chang, L.-H.; Ehrenfild, G.; Rodriguez, L.O.; Hecht, S. M. J. Biol. Chem., 1982, 257, 1606.
10. b) Kenani, A.; Bailly, C.; Helbecque, N; Catteau, J. P.; Houssin, R.; Bernier, J. L.; Henichart, J. P. Eur. J. Chem., 1989, 24, 371.
11. c) Boger, D. L.; Teramoto, S.; Honda, T.; Zhou, J. J. Am. Chem. Soc., 1995, 117, 7338.
12. d) Boger, D. L.;Teramoto, S.; Zhou, J. J. Am. Chem.Soc., 1995, 117, 7344.
13. e) Bailly, C.; Kenani, A.; Waring, M. J. FEBS LETT., 1995, 372, 144 and references are there in.
14. a) Umezawa, H.; Takita, T.; Sugiura, Y.; Otsuka, M.; Kobayashi, S.; Ohno, M. Tetrahedron , 1984, 40, 501.
15. b) Kittaka, A.; Sugano, Y.; Otsuka, M.; Ohno, M. Tetrahedron , 1988, 44, 2811.
16. c) Shinozuka, K.; Morishita, H.; Yamazaki, T.; Sugiura, Y.; Sawai, H. Tetrahedron Lett., 1991, 32, 6869.
17. d) Kouda, J.; Shinozuka, K.; Sawai, H. Tetrahedron Lett., 1995, 36, 5575.
18. Mathes, W.; Sauermilch, W.; Klein, T.Chem. Ber., 1953, 86, 584.
19. Suga, A.; Sugiyama, T.; Otsuka, M.; Ohno, M.; Sugiura, Y.; Maeda, K. Tetrahedron, 1991, 47, 1191.
20. 2O = 4: 1), Electrospray Mass for C18H26N8O5 m/z 403(M+H). Satisfactory NMR spectrum was obtained for the sample.
21. λmax values were observed at 606nm for the I-Cu(II) complex and 595nm for the BLM-Cu(II) complex. EPR g values were observed at g// = 2.200, g⊥. = 2.040, A//(G) = 190 for the I-Cu(II) complex; g// = 2.211, g⊥ = 2.055, A//(G) = 183 for the BLM-Cu(II) complex.
22. Sugiura, Y. J. Am. Chem. Soc., 1980, 102, 5208.
23. Sugiura, Y.; Suzuki, T.; Otsuka, M.; Kobayashi, S.; Ohno, M.; Takita, T.; Umezawa, H. J. Biol. Chem., 1983, 258, 1328.
24. a) Kimura, E.; Kurosaki, H.; Kurogi, Y.; Shionoya, M.; Shiro, M. Inorg. Chem., 1992, 31, 4314.
25. b) Guajordo, R. J.; Chaves, F.; Farinas, E. T.; Mascharak, P. K. J. Am. Chem. Soc., 1995, 117, 3883.
26. -1); v∞ 1557, 1521(carbamoyl), 1651 for I-Fe(II) complex.v∞ 1599, 1624(carbamoyl), 1659 for I-Co(III) complex.