Electrochemical Activation of Oxygenated Fe-Bleomycin

Journal of the American Chemical Society

Volumn 111, Issue 7, 1989, Pages 2722-2724

  Van Atta, Reuel B ^a   Long, Eric C ^c   Hecht, Sidney M ^a   van der Marel, Gijs A ^b   van Boom, Jacques H ^b  

^a UNIVERSITY OF VIRGINIA   (United States)

^b LEIDEN UNIVERSITY   (Netherlands)

^c Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BLEOMYCIN IRON;

DNA CLEAVAGE; DRUG ACTIVATION; ELECTROCHEMISTRY; NONHUMAN;

EID: 0024507081     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00189a061     Document Type: Article

References (17)

1. Metal Ion Activation of Dioxygen; Spiro, T. G., Ed.; Wiley: New York, 1983.
2. (a) Hecht, S. M. Fed. Proc. 1986, 45, 2784. (b) Stubbe, J.; Kozarich, J. W. Chem. Rev. 1987, 87, 1107.
3. Sausville, E. A.; Peisach, J.; Horwitz, S. B. Biochemistry 1978, 17, 2740.
4. Ehrenfeld, G. M.; Rodriguez, L. O.; Hecht, S. M.; Chang, C.; Basus, V. J.; Oppenheimer, N. J. Biochemistry 1985, 24, 81.
5. 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.
6. (a) Heimbrook, D. C.; Mulholland, Jr., R. L.; Hecht, S. M. J. Am. Chem. Soc. 1986, 108, 7839. (b) Heimbrook, D. C.; Carr, S. A.; Mentzer, M. A.; Long, E. C.; Hecht, S. M. Inorg. Chem. 1987, 26, 3835.
7. (a) Kuramochi, H.; Takahashi, K.; Takita, T.; Umezawa, H. J. Antibiot. 1981, 34, 576. (b) Burger, R. M.; Peisach, J.; Horwitz, S. B. J. Biol. Chem. 1981, 256, 11636. (c) Sugiyama, H.; Kilkuskie, R. E.; Hecht, S. M.; van der Marel, G. A.; van Boom, J. H. J. Am. Chem. Soc. 1985, 107, 7765.
8. Sugiyama, H.; Kilkuskie, R. E.; Chang, L.-H.; Ma, L.-T.; Hecht, S. M.; van der Marel, G. A.; van Boom, J. H. J. Am. Chem. Soc. 1986, 108, 3852.
9. Povirk, L. F. Biochemistry 1979, 18, 3989.
10. Hu, I.-F.; Karweik, D. H.; Kuwana, T. J. Electroanal. Chem. 1985, 188, 59.
11. See, also: Fultz, M. L., Ph.D. Thesis, University of Maryland, 1982.
12. (a) Melnyk, D. L.; Horwitz, S. B.; Peisach, J. Biochemistry 1981, 20, 5327. (b) Dabrowiak, J. C.; Santillo, F. S. J. Electrochem. Soc. 1979, 126, 2091. (c) Miyoshi, K.; Kikuchi, T.; Takita, T.; Murato, S.; Ishizu, K. Inorg. Chim. Acta 1988, 151, 45.
13. An analogous observation has been made for reduced Mn porphyrins. See: (a) Creager, S. E.; Raybuck, S. A.; Murray, R. W. J. Am. Chem. Soc. 1986, 108, 4225. (b) Creager, S. E.; Murray, R. W. Inorg. Chem. 1987, 26, 2612.
14. Burger, R. M.; Blanchard, J. S.; Horwitz, S. B.; Peisach, J. J. Biol. Chem. 1985, 260, 15406.
15. Carter, M. T.; Bard, A. J. J. Am. Chem. Soc. 1987, 109, 7528.
16. That this was not due to physical exclusion of the DNA-bound Fe· BLM from the electrode surface was suggested by a parallel observation in other BLM activating systems. See: (a) Burger, R. M.; Peisach, J.; Blumberg, W. E.; Horwitz, S. B. J. Biol. Chem. 1979, 254, 10906. (b) Albertini, J.-P.; Garnier-Suillerot, A.; Tosi, L. Biochem. Biophys. Res. Commun. 1982, 104, 557. (c) Ciriolo, M. R.; Magliozzo, R. S.; Peisach, J. J. Biol. Chem. 1987, 262, 6290. A slight shift in the redox potential of Fe·BLM to a more negative value was observed by differential pulse polargraphy upon admixture of moderate concentrations of DNA. The significance of this observation is unclear, however, since the current obtained from 0.16 mM Fe·BLM and high concentrations (14 mM) of sonicated calf thymus DNA was <1.5% of that obtained in its absence.
17. For another approach, see: Nakamura, M.; Peisach, J. J. Antibiot. 1988. 41. 638.