Dioxygen activation of iron bleomycin and the cleavage of DNA

International Congress Series

Volumn 1233, Issue C, 2002, Pages 511-517

  Peisach, Jack ^a  

^a ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

Author keywords

Bleomycin; DNA cleavage; Oxygen activation

Indexed keywords

EID: 33845571609     PISSN: 05315131     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0531-5131(02)00270-4     Document Type: Article

References (37)

1. Lazo, J.S., Chabner, B.A., Bleomycin. Chabner, B.A., Longo, D.L., (eds.) Cancer Chemotherapy and Biotherapy: Principles and Practice, 1996, Lippincot-Raven Publ, New York, 379–393.
2. Lassoued, K., Clauvel, J.P., Janier, M., Picard, C., Matheron, S., Treatment of the acquired immune deficiency syndrome-related Kaposi's sarcoma with bleomycin as a single agent. Cancer 66 (1990), 1869–1872.
3. Remick, S.C., Reddy, M., Herman, D., Grace, C., Harper, G., Willis, K., Candon, B., Continuous infusion bleomycin in AIDS-related Kaposi's sarcoma. J. Clin. Oncol. 12 (1994), 1130–1136.
4. Nagai, N., Yamaki, H., Suzuki, H., Tanaka, N., Umerzawa, H., The combined effects of bleomycin and sulfhydryl compounds on the thermal denaturation of DNA. Biochim. Biophys. Acta 179 (1969), 165–171.
5. Wu, J.C., Kozarich, J.W., Stubbe, J., Mechanism of bleomycin: evidence for a rate-determining 4′-hydrogen abstraction from poly(dA–dU) associated with the formation of both free base and base propenal. J. Biol. Chem. 256 (1983), 8608–8615.
6. 2. Evidence for intercalation using 2D NMR. Biochemistry 24 (1985), 7562–7568.
7. Magliozzo, R.S., Peisach, J., Ciriolo, M.R., Transfer RNA is cleaved by activated bleomycin. Mol. Pharmacol. 35 (1989), 428–432.
8. Carter, B.J., DeVroom, E., Long, E.C., van der Marel, G.A., von Boom, J.H., Hecht, S.M., Site specific cleavage of RNA by Fe(II)-bleomycin. Proc. Natl. Acad. Sci. U. S. A. 87 (1990), 9373–9377.
9. Ciriolo, M.R., Magliozzo, R.S., Peisach, J., A comparative study of the interactions of bleomycin with nuclei and purified DNA. J. Biol. Chem. 264 (1989), 1443–1449.
10. Stubbe, J., Kozarich, J.W., Mechanisms of bleomycin-induced DNA degradation. Chem. Rev. 87 (1987), 1107–1136.
11. Claussen, C.A., Long, E.C., Nucleic acid recognition by metal complexes of bleomycin. Chem. Rev. 199 (1999), 2797–2816.
12. Burger, R.M., Cleavage of nucleic acids by bleomycin. Chem. Rev. 98 (1998), 1153–1169.
13. Carter, B.J., Murty, V.S., Reddy, K.S., Wang, S.N., Hecht, S.M., A role for the metal binding domain in determining the DNA sequence selectivity of Fe-bleomycin. J. Biol. Chem. 265 (1990), 4193–4196.
14. Povirk, L.F., Hogan, M., Dattagupta, N., Binding of bleomycin to DNA: intercalation of the bithiazole rings. Biochemistry 18 (1979), 96–101.
15. Dabrowiak, J.C., The coordination chemistry of bleomycin: a review. J. Inorg. Biochem. 13 (1980), 317–337.
16. Hecht, S.M., RNA degradation by bleomycin, a naturally occurring bioconjugate. Bioconjugate Chem. 5 (1994), 513–526.
17. Sausville, E.A., Peisach, J., Horwitz, S.B., A role for ferrous ion and oxygen in the degradation of DNA by bleomycin. Biochem. Biophys. Res. Commun. 73 (1976), 14–822.
18. Sausville, E.A., Stein, R.W., Peisach, J., Horwitz, S.B., Properties and products of the degradation of DNA by bleomycin and Fe(II). Biochemistry 17 (1978), 2746–2754.
19. 2. J. Biol. Chem. 254 (1979), 12299–12302.
20. D'Andrea, A.D., Haseltine, W.A., Sequence specific cleavage of DNA by the antibiotics neocarzinostatin and bleomycin. Proc. Natl. Acad. Sci. U. S. A. 75 (1978), 3608–3612.
21. Takeshita, M., Grollman, A.P., Ohtsubo, E., Hotsubo, H., Interaction of bleomycin with DNA. Proc. Natl. Acad. Sci. U. S. A. 75 (1978), 5983–5987.
22. Povirk, L.F., Wubter, W., Kohnlein, W., Hutchinson, F., DNA double-strand breaks and alkali-labile bonds produced by bleomycin. Nucleic Acids Res. 4 (1977), 3573–3580.
23. 2 on the reactions of activated bleomycin. J. Biol. Chem. 257 (1982), 8612–8614.
24. Burger, R.M., Peisach, J., Horwitz, S.B., Stiochiometry of DNA strand scission and aldehyde formation by bleomycin. J. Biol. Chem. 257 (1982), 8612–8614.
25. Burger, R.M., Berkowitz, A.R., Peisach, J., Horwitz, S.B., Origin of malondialdehyde from DNA degraded by Fe(II)-bleomycin. J. Biol. Chem. 25 (1980), 11832–11838.
26. Ciriolo, M.R., Magliozzo, R.S., Peisach, J., Microsome-stimulated activation of ferrous bleomycin in the presence of DNA. J. Biol. Chem. 262 (1987), 6290–6295.
27. R.M. Burger, J. Peisach, S.B. Horwitz, Activated bleomycin: a transient complex of drug, iron and oxygen that degrades DNA. J. Biol. Chem. 256: 11636–11644.
28. Sam, J.W., Tang, X.-J., Magliozzo, R.S., Peisach, J., Electrospray mass spectrometry of iron bleomycin: II. Investigation of the reaction of Fe(III)-bleomycin with iodosylbenzene. J. Am. Chem. Soc. 117 (1995), 1012–1018.
29. Burger, R.M., Blanchard, J.S., Horwitz, S.B., Peisach, J., The redox state of activated bleomycin. J. Biol. Chem. 260 (1985), 15406–15409.
30. Burger, R.M., Kent, T.A., Horwitz, S.B., Munck, E., Peisach, J., Mossbauer study of iron bleomycin and its activation intermediates. J. Biol. Chem. 258 (1993), 1559–1564.
31. Sam, J.W., Peisach, J., EPR spectroscopic investigation of the lability of oxygen in activated bleomycin: implications for the mechanism of BLM-mediated DNA degradation. Biochemistry 32 (1993), 1488–1491.
32. Sam, J.W., Tang, X.-J., Peisach, J., Electrospray mass spectrometry of iron bleomycin: demonstration that activated bleomycin is a ferric peroxide complex. J. Am. Chem. Soc. 116 (1994), 5250–5256.
33. Pratviel, G., Bernadou, J., Meunier, B., Evidence of high-valent iron-oxo species active in the DNA breaks mediated by iron bleomycin. Biochem. Pharmacol. 38 (1989), 133–140.
34. Murugesan, N., Hecht, S.M., Bleomycin as an oxene transferase. Catalytic oxygen transfer to olefins. J. Am. Chem. Soc. 107 (1985), 493–500.
35. Huttenhofer, A., Hudson, S., Noller, H.F., Mascharak, P.K., Cleavage of tRNA by Fe(II)-bleomycin. J. Biol. Chem. 267 (1992), 24471–24475.
36. Rabow, L.E., McGall, G.H., Stubbe, J., Kozarich, J.W., Identification of the source oxygen in the alkaline-labile product accompanying cytosine release during bleomycin-mediated oxidative degradation of d(CGCGCG). J. Am. Chem. Soc. 112 (1990), 3203–3208.
37. II-bleomycin. J. Am. Chem. Soc. 113 (1991), 2290–2295.