On the role of copper and iron in DNA cleavage by ochratoxin A. Structure-activity relationships in metal binding and copper-mediated DNA cleavage

Canadian Journal of Chemistry

Volumn 76, Issue 6, 1998, Pages 907-918

  Ardus, Jason A ^a   Gillman, Ivan G ^a   Manderville, Richard A ^a  

^a WAKE FOREST UNIVERSITY   (United States)

Author keywords

1,10 phenanthroline; Copper; DNA cleavage; Iron; Ochratoxin

Indexed keywords

5 CHLORO 2 HYDROXY N PHENYLALANINEBENZAMIDE; COPPER; COPPER DERIVATIVE; DNA; FERRIC OXIDE; IRON; OCHRATOXIN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DNA BINDING; DNA DAMAGE; FLUORESCENCE SPECTROSCOPY; GENOTOXICITY; METAL BINDING; MOLECULAR INTERACTION; OXIDATION REDUCTION REACTION; STRUCTURE ACTIVITY RELATION;

EID: 0031765155     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v98-088     Document Type: Article

References (57)

1. K.J. van der Merwe, P.S. Steyn, L. Fourie, D.B. Scott, and J.J. Theron. Nature (London), 205, 1112 (1965).
2. (a) T. Kuiper-Goodman and P.M. Scott. Biomed. Environ. Sci. 2, 179 (1989)
3. (b) A.E. Pohland, S. Nesheim, and L. Friedman. Pure Appl. Chem. 64, 1029 (1992).
4. (a) A.M. Bendele, W.W. Carlton, P. Krogh, and E.B. Lillehoj. J. Natl. Cancer Inst. 75, 733 (1985)
5. (b) M. Castegnaro, R. Plestina, G. Dirheimer, I.N. Chernozemsky, and H. Bartsch. Mycotoxins, Endem. Nephropathy Urinary Tract Tumours. Vol. 115. IARC Sci. Publ., Oxford Univ. Press, Oxford, U.K. 1991
6. (c) R.R. Marquardt and A.A. Frohlich. J. Anim. Sci. 70, 3968 (1992).
7. (a) Y. Grosse, I. Baudrimont, M. Castegnaro, A.-M. Betbeder, E.E. Creppy, G. Dirheimer, and L.A. Pfohl. Chem. Biol. Interact. 95, 175 (1995)
8. (b) P.S. Obrecht, Y. Grosse, L.A. Pfohl, and G. Dirheimer. Arch. Toxicol. 70, 244 (1996).
9. (a) E.E. Creppy, A. Kane, G. Dirheimer, C. Lafarge-Frayssinet, S. Mousset, and C. Frayssinet. Toxicol. Lett. 28, 29 (1985)
10. (b) J.C. Seegers, L.H. Bohmer, M.C. Kruger, M.L. Lottering, and K.M. de A. Toxicol. Appl. Pharmacol. 129, 1 (1994).
11. C. Malaveille, G. Brun, and H. Bartsch. Mutat. Res. 307, 141 (1994).
12. H. Xiao, S. Madhyastha, R.R. Marquardt, S. Li, J.K. Vodela, A.A. Frohlich, and B.W. Kemppainen. Toxicol. Appl. Pharmacol. 137, 182 (1996).
13. (a) G.E. de Groene, I.G. Hassing, M.J. Blom, W. Seinen, G.J. Fink, and G.J. Horbach. Cancer Res. 56, 299 (1996)
14. (b) R.F. Omar, H.V. Gelboin, and A.D. Rahimtula. Biochem. Pharmacol. 51, 207 (1996).
15. I. Baudrimont, A.-M. Betbeder, A. Gharbi, L.A. Pfohl, G. Dirheimer, and E.E. Creppy. Toxicology, 89, 101 (1994).
16. B.B. Hasinoff, A.D. Rahimtula, and R.F. Omar. Biochim. Biophys. Acta, 1036, 78 (1990).
17. (a) D. Hoehler, R.R. Marquardt, A.R. McIntosh, and H. Xiao. J. Biol. Chem. 271, 27 388 (1996)
18. (b) D. Hoehler, R.R. Marquardt, A.R. McIntosh, and G.M. Hatch. Biochim. Biophys. Acta, 1357, 225 (1997).
19. (a) A.D. Rahimtula, J.C. Bereziat, V. Bussacchini-Griot, and H. Bartsch. Bioehem. Pharmacol. 37, 4469 (1988)
20. (b) R.F. Omar, A.D. Rahimtula, and H. Bartsh. J. Biochem. Toxicol. 6, 203 (1991).
21. (a) R.T. Scannell, J.R. Barr, V.S. Murty, K.S. Reddy, and S.M. Hecht. J. Am. Chem. Soc. 110, 3650 (1988)
22. (b) U.S. Singh, R.T. Scannell, H. An, B.J. Carter, and S.M. Hecht. J. Am. Chem. Soc. 117, 12691 (1995).
23. (a) Y. Li and M.A. Trush. Carcinogenesis, 14, 1303 (1993)
24. (b) Cancer Res. 54, 1895s (1994).
25. (a) D.S. Sigman. Acc. Chem. Res. 19,180 (1986)
26. (b) T.B. Thederahn, M.D. Kuwabara, T.A. Larsen, and D.S. Sigman. J. Am. Chem. Soc. 111, 4941 (1989).
27. J. Blair and G.T. Newbold. J. Chem. Soc. 2871 (1955).
28. (a) M. Watanabe, M. Sahara, M. Kubo, S. Furukawa, R.J. Billedeau, and V. Snieckus. J. Org. Chem. 49, 742 (1984)
29. (b) M.P. Sibi, S. Chattopadyyay, J.W. Dankwardt, and V. Snieckus. J. Am. Chem. Soc. 107, 6312 (1985).
30. S. Terao, M. Shiraishi, K. Kato, S. Ohkawa, Y. Ashida, and Y. Maki. J. Chem. Soc. Perkin Trans, 1, 2909 (1982).
31. H. Xiao, R.R. Marquart, A.A. Frohlich, and Y.Z. Ling. J. Agric. Food Chem. 43, 524 (1995).
32. (a) C. Scatchard. Ann. N.Y. Acad. Sci. 51, 660 (1949)
33. (b) K.A. Conners. Binding constants. The measurement of molecular complex stability. John Wiley & Sons, New York. 1987. pp. 339-343.
34. F.A. Cotton and G. Wilkinson. Advanced inorganic chemistry. A comprehensive text. 4th ed. John Wiley & Sons, New York. 1980.
35. F.S. Chu. Arch. Biochem. Biophys. 147, 359 (1971).
36. F.S. Chu. CRC Crit. Rev. Toxicol. 2, 499 (1974).
37. A. Albert and E.P. Sergeant. The determination of ionization constants. Chapman & Hall, London. 1962.
38. W. Knapp Pogozelski, T.J. McNeese, and T.D. Tullius. J. Am. Chem. Soc. 117, 6428 (1995).
39. I.M.C.M. Rietjens, C. den Besten, R.P. Hanzlik, and P.J. van Bladeren. Chem. Res. Toxicol. 10, 629 (1997).
40. M.W. Bredenkamp, J.L.M. Dillen, P.M. van Rooyen, and P.S. Steyn. J. Chem. Soc. Perkin Trans. 2, 1835 (1989).
41. H. Sigel and R.B. Martin. Chem. Rev. 82, 385 (1982).
42. (a) J. Balla, P.V. Bernhardt, P. Buglyo, P. Comba, T.W. Hambley, R. Schmidlin, S. Stebler, and K. Varnagy. J. Chem. Soc. Dalton Trans. 277 (1991)
43. (b) F.V Pamatong, C.A. Detmer III, and J.B. Bocarsly. J. Am. Chem. Soc. 118, 5339 (1996).
44. A. Stassinopoulos, G. Schulte, G.C. Papaefthymiou, and J.P. Caradonna. J. Am. Chem. Soc. 113, 8686 (1991).
45. (a) D.P. Mack, B.L. Iverson, and P.B. Dervan. J. Am. Chem. Soc. 110, 7572 (1988)
46. (b) C. Harford and B. Sarkar. Acc. Chem. Res. 30, 123 (1997).
47. H. Lund and M.M Baizer (Editors). Organic electrochemistry, an introduction and a guide. 3rd ed. Revised and expanded. Marcel Dekker, Inc., New York. 1991. pp. 615-635.
48. (a) K. Takehira, M. Shimiza, Y. Watanabe, H. Orita, and T. Hayakawa. J. Chem. Soc. Chem. Commun. 1705 (1989)
49. (b) Y. Takizawa, T. Munakata, Y. Iwasa, and T. Mitsuhashi. J. Org. Chem. 50, 4383 (1985).
50. (a) T. Ohe, T. Mashino, and M. Hirobe. Tetrahedron Lett. 36, 7681 (1995)
51. (b) V.M. Samokyszyn, J.P. Freeman, K.R. Maddipati, and R. Lloyd. Chem. Res. Toxicol. 9, 1368 (1996).
52. (a) Y.J. Abul-Hajj, K. Tabakovic, and I. Tabakovic. J. Am. Chem. Soc. 117, 6144 (1995)
53. (b) M.A. Lewis, D.G Yoerg, J.L. Bolton, and J.A. Thompson. Chem. Res. Toxicol. 9, 1368 (1996).
54. D. Parsonage, H. Miller, R.P. Ross, and A. Claiborne. J. Biol. Chem. 268, 3161 (1993).
55. S.O. de Silva, M. Watanabe, and V. Snieckus. J. Org. Chem. 44, 4802 (1979).
56. H. Benesi and J.H. Hildebrand. J. Am. Chem. Soc. 71, 2703 (1949).
57. C.K. Mirabelli, C.H. Huang, and S.T. Crooke. Cancer Res. 40, 4173 (1980).