Bleomycin versus OH-radical-induced malonaldehydic-product formation in DNA

International Journal of Radiation Biology

Volumn 75, Issue 1, 1999, Pages 101-109

  Rashid, R ^a   Langfinger, D ^a   Wagner, R ^a   Schuchmann, H P ^a   Von Sonntag, C ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACROLEIN DERIVATIVE; ADENINE; BLEOMYCIN; CYTOSINE; DNA; GUANINE; HYDROXYL RADICAL; IRON; MALONALDEHYDE; OXYGEN; THIOBARBITURIC ACID; THYMIDINE; THYMINE;

ARTICLE; CONTROLLED STUDY; DERIVATIZATION; DRUG MECHANISM; GAMMA IRRADIATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IONIZING RADIATION; MASS SPECTROMETRY; NONHUMAN; OXIDATION; PH; PRIORITY JOURNAL; RADIOLYSIS;

ANIMALS; ANTI-BACTERIAL AGENTS; BLEOMYCIN; CATTLE; DNA; GAMMA RAYS; HYDROXYL RADICAL; MALONDIALDEHYDE; OXIDATION-REDUCTION;

EID: 0032962139     PISSN: 09553002     EISSN: None     Source Type: Journal    
DOI: 10.1080/095530099140852     Document Type: Article

References (57)

1. ABSALON, M. J., KOZARICH, J. W. and STUBBE, J., 1995a, Sequence-specific double-strand cleavage of DNA by Fe-bleomycin. I. The detection of sequence-specific double-strand breaks using hairpin oligonucleotides. Biochemistry 34, 2065-2075.
2. ABSALON, M. J., KRISHNAMOORTHY, C. R., McGALL, G., KOZARICH, J. W. and STUBBE, J., 1992, Bleomycin mediated degradation of DNA RNA hybrids does not involve C-1′ chemistry. Nucleic Acids Research, 20, 4179-4185.
3. ABSALON, M. J., WU, W., KOZARICH, J. W. and STUBBE, J., 1995b, Sequence-specific double-strand cleavage of DNA by Fe-bleomycin. 2. Mechanism and dynamics. Biochemistry, 34, 2076-2086.
4. 17O nuclear magnetic resonance study. Journal of the American Chemical Society, 112, 4058-4060.
5. BREEN, A. B. and MURPHY, J. A., 1995, Reactions of oxyl radicals with DNA. Free Radicals in Biology and Medicine, 18, 1033-1077.
6. BURGER, R. A., 1998, Cleavage of nucleic acids by bleomycin. Chemical Reviews, 98, 1153-1169.
7. BURGER, R. M. and DRLICA, K., 1996, Bleomycin reaction pathways: kinetic approaches. In: DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Disease, edited by B. Meunier (Dordrecht: Kluwer), 12, 91.
8. BURGER, R. M., BERKOWITZ, A. R., PEISACH, J. and HORWITZ, S. B., 1980, Origin of malondialdehyde from DNA degraded by Fe(II)-bleomycin. Journal of Biological Chemistry, 255, 11832-11838.
9. BURGER, R. M., DRLICA, K. and BIRDSALL, B., 1994, The DNA cleavage pathway of iron bleomycin. Journal of Biological Chemistry, 269, 25978-25985.
10. BURGER, R. M., PEISACH, J. and HORWITZ, S. B., 1981, Activated bleomycin. A transient complex of drug, iron, and oxygen that degrades DNA. Journal of Biological Chemistry, 256, 11636-11644.
11. 2 on the reactions of activated bleomycin. Journal of Biological Chemistry, 257, 3372-3375.
12. BURGER, R. M., PEISACH, J. and HORWITZ, S. B., 1982b, Stoichiometry of DNA strand scission and aldehyde formation by bleomycin. Journal of Biological Chemistry, 257, 8612-8614.
13. BURGER, R. M., PROJAN, S. J., HORWITZ, S. B. and PEISACH, J., 1986, The DNA cleavage mechanism of iron-bleomycin. Journal of Biological Chemistry, 261, 15955-15959.
14. BURGER, R. M., TIAN, G. and DRLICA, K., 1995, Oxygen isotope effect on activated bleomycin stability. Journal of the American Chemical Society, 117, 1167-1168.
15. DEDON, P. C. and GOLDBERG, I. H., 1992, Free-radical mechanisms involved in the formation of sequence-dependent bistranded DNA lesions by the antitumor antibiotics bleomycin, neocarzinostatin, and calicheamicin. Chemical Research in Toxicology, 5, 311-332.
16. FEIG, A. L. and LIPPARD, S. J., 1994, Reactions of non-heme iron(II) centers with dioxygen in biology and chemistry. Chemical Reviews, 94, 759-805.
17. 2. Journal of the American Chemical Society, 117, 6146-6147.
18. GIESE, B., BEYRICH-GRAF, X., ERDMANN, P., PETRETTA, M. and SCHWITTER, U., 1995b, The chemistry of single-stranded 4′-DNA radicals: influence of the radical precursor on anaerobic and aerobic strand cleavage. Chemistry and Biology, 2, 367-375.
19. GIESE, B., DUSSY, A., MEGGERS, E., PETRETTA, M. and SCHWITTER, U., 1997, Conformation, lifetime, and repair of 4′-DNA radicals. Journal of the American Chemical Society, 119, 11130-11131.
20. GILONI, L., TAKESHITA, M., JOHNSON, F., IDEN, C. and GROLLMAN, A. P., 1981, Bleomycin-induced strand-scission of DNA. Mechanism of deoxyribose cleavage. Journal of Biological Chemistry, 256, 8608-8615.
21. GROLLMAN, A. P., 1988, Base propenals and the toxicity of bleomycin. Reviews in Oncology, 53, 79-90.
22. GUTTERIDGE, J. M. C., 1982, Free-radical damage to lipids, amino acids, carbohydrates and nucleic acids determined by thiobarbituric acid reactivity. International Journal of Biochemistry, 14, 649-653.
23. GUTTERIDGE, J. M. C. and SHUTE, D. J., 1981, Iron-dioxygen-dependent changes to the biological activities of bleomycin. Journal of Inorganic Biochemistry, 15, 349-357.
24. GUTTERIDGE, J. M. C. and TOEG, D., 1982, Iron-dependent free radical damage to DNA and deoxyribose. Separation of TBA-reactive intermediates. International Journal of Biochemistry, 14, 891-893.
25. HARTMANN, V., VON SONNTAG, C. and SCHULTE-FROHLINDE, D., 1970, γ-Radiolyse von 2-Desoxy-D-ribose in wäßriger Lösung. Zeitschrift für Naturforschung, Teil b, 25, 1394-1404.
26. HECHT, S. M., 1979, Bleomycin: Chemical, biochemical and biological aspects (Berlin: Springer).
27. HECHT, S. M., 1986, DNA strand scission by activated bleomycin group antibiotics. Federation Proceedings, 45, 2784-2791.
28. HECHT, S. M., LONG, E. C., VAN ATTA, R. B., DE VROOM, E. and CARTER, B. J., 1990, On the mechanism of bleomycin activation and polynucleotide strand scission. In Molecular Mechanisms in Bioorganic Processes, edited by C. Bleasdale and B. T. Golding (London: Royal Society of Chemistry), pp. 100-114.
29. JANICEK, M. F., HASELTINE, W. A. and HENNER, W. D., 1985, Malondialdehyde in gamma-irradiated DNA, deoxynucleotides and deoxynucleosides. Nucleic Acids Research, 13, 9011-9029.
30. KAKAC, B. and VEJDELEK, Z. J., 1974, Handbook der photometrischen Analyse organischer Verbindungen, Vol. 1 (Weinheim: Verlag Chemie), pp. 239-242.
31. KAPP, D. S. and SMITH, K. C., 1970, Chemical nature of chain breaks in DNA by X-irradiation in vitro. Radiation Research, 42, 34-49.
32. KOU, M. T. and HAIDLE, C. W., 1973, Characterization of chain breakage in DNA induced by bleomycin. Biochimica Biophysica. Acta, 335, 109-114.
33. KRUSHINSKAYA, N. P., 1983, Radiation-induced chemical alterations in sugar moiety of DNA: Carbon - carbon bond rupture. In: Proceedings of the 5th Tihany Symp. Radiation Chemistry, edited by J. Dobo, P. Hedvig and R. Schiller (Budapest: Akademiai Kiado), pp. 1061-1066.
34. KRUSHINSKAYA, N. P. and SHALNOV, M. I., 1967, Nature of breaks in the DNA chain upon irradiation of aqueous solutions. Radiobiology, 7, 36-45.
35. LANGFINGER, D. and VON SONNTAG, C., 1985, γ-Radiolysis of 2′-deoxyguanosine. The structure of the malondialdehyde-like product. Zeitschrift für Naturforschung. Teil c, 40, 446-448.
36. LOEB, K. E., ZALESKI, J. M., WESTRE, T. E., GUAJARDO, R. J., MASCHARAK, P. K., HEDMAN, B., HODGSON, K. O. and SOLOMON, E. I., 1995, Spectroscopic definition of the geometric and electronic structure of the non-heme iron active site in iron(II) bleomycin: correlation with oxygen reactivity. Journal of the American Chemical Society, 117, 4545-4561.
37. McGALL, G. H., RABOW, L. E., ASHLEY, G. W., WU, S. H., KOZARICH, J. W. and STUBBE, J., 1992, New insight into the mechanism of base propenal formation during bleomycin-mediated DNA degradation. Journal of the American Chemical Society, 114, 4958-4967.
38. MURUGESAN, N., XU, C., EHRENFELD, G. M., SUGIYAMA, H., KILKUSKIE, R. E., RODRIGUEZ, L. O., CHANG, L.-H. and HECHT, S. M., 1985, Analysis of products formed during bleomycin-mediated DNA degradation. Biochemistry, 24, 5735-5744.
39. MÜLLER, W. E. G., YAMAZAKI, Z.-I., BRETER, H. J. and ZAHN, R. K., 1972, Action of bleomycin on DNA and RNA. European Journal of Biochemistry, 31, 518-525.
40. NATRAJAN, A. and HECHT, S. M., 1994, Bleomycins: mechanism of polynucleotide recognition and oxydative degradation. In: Molecular Aspects of Anticancer Drug-DNA Interactions, edited by S. Neidle and M. Waring, Vol. 2 (London: MacMillan), pp. 197-242.
41. OWA, T., SUGIYAMA, T., OTSUKA, M. and OHNO, M., 1990, A model study on the mechanism of the autoxidation of bleomycin. Tetrahedron Letters, 31, 6063-6066.
42. POVIRK, L. S., HAN, Y.-H. and STEIGHNER, R. J., 1989, Structure of bleomycin-induced DNA double-strand breaks: predominance of blunt ends and single-base 5′-extensions. Biochemistry, 28, 5808-5814.
43. POVIRK, L. F., 1996, DNA damage and mutagenesis by radiomimetic DNA-cleaving agents: bleomycin, neocarzinostatin and other enediynes. Mutation Research, 355, 71-89.
44. SAM, J. W., TANG, X.-J. and PEISACH, J., 1994, Electrospray mass spectrometry of iron bleomycin: demonstration that activated bleomycin is a ferric peroxide complex. Journal of the American Chemical Society 116, 5250-5256.
45. SAUSVILLE, E. A. and HORWITZ, S. B., 1979, A mechanism for the degradation of DNA by bleomycin. In: Bristol-Myers Cancer Symposia, edited by M. Gordon and S. T. Crooke (New York: Academic Press), pp. 181-205.
46. SCHULTE-FROHLINDE, D. and VON SONNTAG, C., 1990, Sugar lesions in cell radiobiology. In: Ionizing Radiation Damage to DNA: Molecular Aspects, edited by S. S. Wallace and R. B. Painter, Proceedings of the Radiation Research Society UCLA, Lake Tahoe, Calif. Jan. 16-21 (New York: Wiley), pp. 31-42.
47. STEIGHNER, R. J. and POVIRK, L. F., 1990, Bleomycin-induced DNA lesions at mutational hot spots: Implications for the mechanism of double-strand cleavage. Proceedings of the National Academy of Science, 87, 8350-8354.
48. STUBBE, J. and KOZARICH, J. W., 1987, Mechanism of bleomycin-induced DNA degradation. Chemical Reviews, 87, 1107-1136.
49. STUBBE, J., KOZARICH, J. W., WU, W. and VANDERWALL, D. E., 1996, Bleomycins: a structural model for specificity, binding, and double strand cleavage. Accounts Chemical Research, 29, 322-330.
50. SUGIYAMA, H., KILKUSKIE, R. E., CHANG, L.-H., MA, L. T., HECHT, S. M., van der Marel, G. A. and VAN BOOM, J. H., 1986, DNA strand scission by bleomycin: catalytic cleavage and strand selectivity. Journal of the American Chemical Society, 108, 3852-3854.
51. ULANSKI, P., BOTHE, E., HILDENBRANDT, K., VON SONNTAG, C. and ROSIAK, J. M., 1997, The influence of repulsive electrostatic forces on the lifetimes of poly(acrylic acid) radicals in aqueous solution. Nucleonika, 42, 425-436.
52. ULLRICH, M. and HAGEN, U., 1971, Base liberation and concomitant reactions in irradiated DNA solutions. International Journal of Radiation Biology, 19, 507-517.
53. VON SONNTAG, C., 1987, The Chemical Basis of Radiation Biology (London: Taylor and Francis).
54. VON SONNTAG, C., 1994, Topics in free-radical-mediated DNA damage: purines and damage amplification superoxide reactions bleomycin, the incomplete radiomimetic. International Journal of Radiation Biology, 66, 485-490.
55. VON SONNTAG, C. and SCHUCHMANN, H.-P., 1997, Peroxyl radicals in aqueous solutions. In Peroxyl Radicals, edited by Z. B. Alfassi (London: Wiley), pp. 173-234.
56. WU, Y.-D., HOUK, K. N., VALENTINE, J. S. and NAM, W., 1992, Is intramolecular hydrogen-bonding important for bleomycin reactivity? A molecular mechanics study. Inorganic Chemistry, 31, 718-720.
57. WU, J. C., KOZARICH, J. W. and STUBBE, J., 1985, 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. Biochemistry, 24, 7562-7568.