Disproportionation and nuclease activity of bis[2-ethyl-2-hydroxybutanoato(2-)]oxochromate(V) in neutral aqueous solutions

Inorganic Chemistry

Volumn 39, Issue 3, 2000, Pages 385-395

  Levina, Aviva ^a   Lay, Peter A ^a   Dixon, Nicholas E ^b  

^a UNIVERSITY OF SYDNEY   (Australia)

^b AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BIS(2 HYDROXY 2 ETHYLBUTANOATO)OXOCHROMATE(V); BIS(2-HYDROXY-2-ETHYLBUTANOATO)OXOCHROMATE(V); BIS[2 ETHYL 2 HYDROXYBUTANOATE]OXOCHROMATE; CARCINOGEN; CHROMIUM; CHROMIUM DERIVATIVE; CIRCULAR DNA; DNA; MANGANESE; NUCLEASE; ORGANOMETALLIC COMPOUND; PHOSPHATE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DNA CLEAVAGE; DNA DAMAGE; DNA SUPERCOILING; DRUG ACTIVITY; ENZYME ACTIVITY; KINETICS; MODEL; MOLECULAR MODEL; PH; PLASMID; REACTION ANALYSIS; SOLUTION AND SOLUBILITY; SPECTROSCOPY; STOICHIOMETRY; ULTRAVIOLET SPECTROPHOTOMETRY;

CARCINOGENS; CHROMIUM COMPOUNDS; DNA DAMAGE; DNA, CIRCULAR; DNA, SUPERHELICAL; HYDROGEN-ION CONCENTRATION; KINETICS; MANGANESE; MODELS, CHEMICAL; ORGANOMETALLIC COMPOUNDS; PLASMIDS; SOLUTIONS; SPECTROPHOTOMETRY, ULTRAVIOLET; SUPPORT, NON-U.S. GOV'T; WATER;

EID: 0034614852     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic990729c     Document Type: Article

References (66)

1. Abbreviations: DMSO = dimethyl sulfoxide; ehba = 2-ethyl-2-hydroxybutanoate(2-); HEPES = 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid; SSB = single strand breaks; SVD = singular value decomposition; Tris = tris(hydroxymethyl)aminomethane; bis-Tris = [bis(hydroxyethyl)amino]tris(hydroxymethyl)methane.
2. Krumpolc, M.; Roček, J. J. Am. Chem. Soc. 1979, 101, 3206-3209.
3. Judd, R. J.; Hambley, T. W.; Lay, P. A. J. Chem. Soc., Dalton Trans. 1989, 2205-2210.
4. Farrell, R. P.; Lay, P. A. Comments Inorg. Chem. 1992, 13, 133-175 and references therein.
5. Bose, R. N.; Fonkeng, B.; Barr-David, G.; Farrell, R. P.; Judd, R. J.; Lay, P. A.; Sangster, D. F. J. Am. Chem. Soc. 1996, 118, 7139-7144.
6. Krumpolc, M.; Roček, J. Inorg. Chem. 1985, 24, 617-621.
7. 6
8. Rajasekar, N.; Gould, E. S. Inorg. Chem. 1983, 22, 3798-3801.
9. Connett, P. H.; Wetterhahn, K. E. Struct. Bonding (Berlin) 1983, 54, 93-124.
10. For recent reviews of the problem, see: (a) Cieślak-Golonka, M. Polyhedron 1996, 15, 3667-3689.
11. (b) Kortenkamp, A.; Casadevall, M.; Da Cruz Fresco, P.; Shayer, R. O. J. NATO ASI Ser., Ser. 2 1997, 26, 15-34.
12. (c) Stearns, D. M.; Wetterhahn, K. E. NATO ASI Ser., Ser. 2 1997, 26, 55-72, and references therein.
13. Farrell, R. P.; Judd, R. J.; Lay, P. A.; Dixon, N. E.; Baker, R. S. U.; Bonin, A. M. Chem. Res. Toxicol. 1989, 2, 227-229.
14. Sugden, K. D.; Wetterhahn, K. E. J. Am. Chem. Soc. 1996, 118, 10811-10818.
15. Sugden, K. D.; Wetterhahn, K. E. Chem. Res. Toxicol. 1997, 10, 1397-1406.
16. Bose, R. N.; Fonkeng, B. S.; Moghaddas, S.; Stroup, D. Nucleic Acids Res. 1998, 26, 1588-1596.
17. Levina, A.; Barr-David, G.; Codd, R.; Lay, P. A.; Dixon, N. E.; Hammershøi, A.; Hendry, P. Chem. Res. Toxicol. 1999, 12, 371-381.
18. (a) Pratviel, G.; Bernadou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746-769.
19. (b) Neyhart, G. A.; Kalsbeck, W. A.; Welch, T. W.; Grover, N.; Thorp, H. H. In Mechanistic Bioinorganic Chemistry; Thorp, H. H., Pecoraro, V. L., Eds.; American Chemical Society: Washington, DC, 1995; pp 405-429 and references therein.
20. Ghosh, M. C.; Gelerinter, E.; Gould, E. S. Inorg. Chem. 1992, 31, 702-705.
21. Stearns, D. M.; Wetterhahn, K. E. Chem. Res. Toxicol. 1994, 7, 219-230.
22. Kortenkamp, A.; Casadevall, M.; Faux, S. P.; Jenner, A.; Shayer, R. O. J.; Woodbridge, N.; O'Brien, P. Arch. Biochem. Biophys. 1996, 329, 199-207.
23. Zhang, L. Ph.D. Thesis, University of Sydney, 1998.
24. Stearns, D. M.; Wetterhahn, K. E. Chem. Res. Toxicol. 1997, 10, 271-278.
25. IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Vol. 49. Chromium, Nickel and Welding; International Agency on the Research of Cancer: Lyon, France, 1990.
26. Leonard, A.; Lauwerys, R. R. Mutat. Res. 1980, 75, 49-62.
27. Dillon, C. T.; Lay, P. A.; Bonin, A. M.; Cholewa, M.; Legge, G. J. F.; Collins, T. J.; Kostka, K. L. Chem. Res. Toxicol 1998, 11, 119-129.
28. Barr-David, G.; Charara, M.; Codd, R.; Farrell, R. P.; Irwin, J. A.; Lay, P. A.; Bramley, R.; Brumby, S., Ji, J.-Y.; Hanson, G. R. J. Chem. Soc., Faraday Trans. 1995, 91, 1207-1216.
29. Ghosh, M. C.; Gould, E. S. Inorg. Chem. 1991, 30, 491-494.
30. Codd, R.; Lay, P. A.; Levina, A. Inorg. Chem. 1997, 36, 5440-5448.
31. Buettner, G. R. Methods Enzymol. 1990, 186, 125-127.
32. 15 Therefore, stock solutions of 1 in DMSO were not used in DNA cleavage studies.
33. 4] were within the experimental error (20%).
34. Pro-Kineticist, Version 4.10; Applied Photophysics: Leatherhead, U.K., 1996.
35. Lay, P. A.; Levina, A. Inorg. Chem. 1996, 35, 7709-7717.
36. Chandler, W. D.; Lee, E. J.; Lee, D. G. J. Chem. Educ. 1987, 64, 878-881.
37. Origin. Technical Graphics and Data Analysis for Windows, Version 4.1; Microcal Software: Northampton, MA, 1996.
38. Chemical Kinetics Simulator, Version 1.01; IBM Almaden Research Center: New York, 1996.
39. Mitewa, M.; Bontchev, P. R. Coord. Chem. Rev. 1985, 61, 241-272.
40. 6
41. WIN-EPR, Version 921201; Bruker-Franzen Analytic: Bremen, Germany, 1996.
42. Adobe Photoshop, Version 2.5; Adobe Systems: Mountain View, CA, 1993.
43. Epe, B.; Hegler, J. Methods Enzyol. 1994, 234, 122-131.
44. Brasch, N. E.; Buckingham, D. A.; Evans, A. B.; Clark, C. R. J. Am. Chem. Soc. 1996, 118, 7969-7980.
45. The formation of Cr(VI) phosphate esters has been observed in acidic media (pH ≤ 5): Frennesson, S.-A.; Beattie, J. K.; Haight, G. P. J. Am. Chem. Soc. 1968, 90, 6018-6022.
46. Electrochemical studies have shown that the ligand exchange reactions of Cr(V) complexes are fast (millisecond to second time scale): Bramley, R.; Farrell, R. P.; Ji, J.-Y.; Lay, P. A. Aust. J. Chem. 1990, 43, 263-279. See also refs 3-5.
47. Experimental evidence for the existence of significant amounts of monochelated Cr(V)-ehba complexes in equilibrium with 1 in acidic media (pH 0-4) has been obtained: Farrell, R. P.; Lay, P. A.; Levina, A.; Maxwell, I. A.; Bramley, R.; Brumby, S.; Ji. J.-Y. Inorg. Chem. 1998, 37, 3159-3166. See also refs 4 and 5.
48. Sugden, K. D.; Wetterhahn, K. E. Inorg. Chem. 1996, 35, 3727-3728.
49. Goodgame, D. L. M.; Joy, A. M. Inorg. Chim. Acta 1987, 135, 115-118.
50. Fonkeng, B. S.; Gelerinter, E.; Bose, R. N. J. Chem. Soc., Dalton Trans. 1995, 4129-4130.
51. Lay, P. A.; Levina, A. J. Am. Chem. Soc. 1998, 120, 6704-6714.
52. The solution structure of 2 has been recently determined by EXAFS spectroscopy: Levina, A.; Foran, G. J.; Lay, P. A. J. Chem. Soc., Chem. Commun. 1999, 2339-2340.
53. At λ < 420 nm, the absorbance changes due to the formation of Cr-(IV) intermediates and Cr(III) products were small in comparison to the absorbances of Cr(V) and Cr(VI). Therefore, no reliable spectra of the Cr(IV) and Cr(III) species in this region could be obtained.
54. -1).
55. Such studies could not be performed in phosphate buffers, as concentrations of the buffers would change significantly due to the formation of phosphate-containing Cr(III) products (Figure S3).
56. Henry, E. R.; Hofrichter, J. Methods Enzymol. 1992, 210, 129-192.
57. 15
58. max were estimated by the summation of modeled kinetic curves of [9] and [10].
59. 45 However, phosphate could also bind as a polydentate or bridging ligand (Hathaway, B. J. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, U.K., 1987; Vol. 2, pp 413-434).
60. Espenson, J. H. In Investigation of Rates and Mechanisms of Reactions; Bernasconi, C. F., Ed.; Wiley: New York, 1986; pp 487-563.
61. Hambley, T. W.; Judd, R. J.; Lay, P. A. Inorg. Chem. 1992, 31, 345-351.
62. 27,48
63. Giese, B.; Dussy, A.; Meggers, E.; Petretta, M.; Schwitter, U. J. Am. Chem. Soc. 1997, 119, 11130-11131.
64. ox] is the concentration (M) of DNA oxidation products (found from the kinetic model).
65. Cabelli, D.; Bielski, B. H. J. Methods Enzymol. 1990, 186, 116-120.
66. 25,44