Nickel-dependent oxidative cross-linking of a protein

Chemical Research in Toxicology

Volumn 10, Issue 3, 1997, Pages 302-309

  Gill, Gurpreet ^a   Richter Rusli, Angelika A ^a   Ghosh, Madhushree ^a,b   Burrows, Cynthia J ^a,c   Rokita, Steven E ^a,b  

^a STONY BROOK UNIVERSITY   (United States)

^b Bldg 142   (United States)

^c UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYL RADICAL; MANNITOL; NICKEL; RIBONUCLEASE A; SCAVENGER;

AMINO ACID ANALYSIS; ARTICLE; OLIGOMERIZATION; OXIDATION; PROTEIN CROSS LINKING; REACTION ANALYSIS;

AMINO ACIDS; ANIMALS; CATTLE; CROSS-LINKING REAGENTS; ELECTROPHORESIS, POLYACRYLAMIDE GEL; NICKEL; OXIDATION-REDUCTION; PROTEINS; RIBONUCLEASE, PANCREATIC; TYROSINE;

EID: 0030975553     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx960170i     Document Type: Article

References (70)

1. Costa, M. (1991) Molecular mechanisms of nickel carcinogenesis. Annu. Rev. Pharmacol. Toxicol. 31, 321-327.
2. Kasprzak, K. S. (1991) The role of oxidative damage in metal carcinogenicity. Chem. Res. Toxicol. 4, 604-615.
3. Wetterhahn, K. E., and Dudek, E. J. (1996) Environmental metal carcinogens: genotoxicity and altered gene expression by direct metal-mediated and indirect oxidative pathways. New J. Chem. 20, 199-203.
4. Glennon, J. D., and Sarkar, B. (1982) Nickel(II) transport in human blood serum. Biochem. J. 203, 15-23.
5. Sigel, H., and Martin, R. B. (1982) Coordinating properties of the amide bond. Stability and structure of metal ion complexes of peptides and related ligands. Chem. Rev. 82, 385-426.
6. Hausinger, R. P. (1993) Biochemistry of Nickel, Plenum Press, New York, NY.
7. Bossu, F. P., Chellappa, K. L., and Margerum, D. W. (1977) Ligand effects on the thermodynamic stabilization of copper(III)-peptide complexes. J. Am. Chem. Soc. 99, 2195-2203.
8. Bossu, F. P., Paniago, E. B., Margerum, D. W., and Kirksey, S. T., Jr. (1978) Trivalent nickel catalysis of the autoxidation of nickel(II) tetraglycine. Inorg. Chem. 17, 1034-1042.
9. 2+ in the presence of oligopeptides. Arch. Biochem. Biophys. 299, 154-162.
10. Torreilles, J., and Guerin, M-C. (1990) Nickel(II) as a temporary catalyst for hydroxyl radical generation. FEBS Lett. 272, 58-60.
11. Kasprzak, K. S., and Bare, R. M. (1989) In vitro polymerization of histones by carcinogenic nickel compounds. Carcinogenesis 10, 621-624.
12. Datta, A. K., Misra, M., North, S. L., and Kasprzak, K. S. (1992) Enhancement by nickel II) and L-histidine of 2′-deoxyguanosine oxidation with hydrogen peroxide. Carcinogenesis 13, 283-287.
13. phe and Tetrahymena group I intron. Biochemistry 32, 7610-7616.
14. Burrows, C. J., and Rokita, S. E. (1994) Probing guanine structure in nucleic acid folding using nickel complexes. Acc. Chem. Res. 27, 295-301.
15. Muller, J. G., Paikoff, S. J., Rokita, S. E., and Burrows, C. J. (1994) DNA modification promoted by water-soluble nickel(II) salen complexes: A switch to DNA alkylation. J. Inorg. Biochem. 54, 199-206.
16. Cheng, C.-C., Rokita, S. E., and Burrows, C. J. (1993) Nickel-(III)-promoted DNA scission using ambient dioxygen. Angew. Chem., Int. Ed. Engl. 32, 277-278.
17. phe with Ni(III) and Co(III) complexes of bleomycin. Biochem. Biophys. Res. Commun. 191, 1338-1346.
18. Guan, L. L., Kuwahara, J., and Sugiura, Y. (1993) Guanine-specific binding by bleomycin-nickel(III) complex and its reactivity for guanine-quartet telomeric DNA. Biochemistry 32, 6141-6145.
19. Mack, D. P., and Dervan, P. B. (1990) Nickel-mediated sequence-specific oxidative cleavage of DNA by a designed metalloprotein. J. Am. Chem. Soc. 112, 4604-4606.
20. Mack, D. P., and Dervan, P. B. (1992) Sequence-specific oxidative cleavage of DNA by a designed metalloprotein, Ni(II)-GGH-(Hin139-190). Biochemistry 31, 9399-9405.
21. Shullenberger, D. F., Eason, P. D., and Long, E. C. (1993) Design and synthesis of a versatile DNA-cleaving metallopeptide structural domain. J. Am. Chem. Soc. 115, 11038-11039.
22. Liang, Q., Eason, P. D., and Long, E. C. (1995) Metallopeptide-DNA interactions: Site-selectivity based on amino acid composition and chirality. J. Am. Chem. Soc. 117, 9625-9631.
23. Cuenoud, B., Tarasow, T. M., and Schepartz, A. (1992) A new strategy for directed protein cleavage. Tetrahedron Lett. 33, 895-898.
24. Brown, K. C., Yang, S.-H., and Kodadek, T. (1995) Highly specific oxidative cross-linking of proteins mediated by a nickel-peptide complex. Biochemistry 34, 4733-4739.
25. Heyduk, E., and Heyduk, T. (1994) Mapping protein domains involved in macromolecular interactions: a novel protein foot-printing approach. Biochemistry 33, 9643-9650.
26. Rana, T. M., and Meares, C. F. (1990) Specific cleavage of a protein by an attached iron chelate. J. Am. Chem. Soc. 112, 2457-2458.
27. Rana, T. M., and Meares, C. F. (1991) Transfer of oxygen from an artificial protease to peptide carbon during proteolysis. Proc. Natl. Acad. Sci. U.S.A. 88, 10578-10582.
28. Schepartz, A., and Cuenoud, B. (1990) Site-specific cleavage of the protein calmodulin using a trifluoperazine-based affinity reagent. J. Am. Chem. Soc. 112, 3247-3249.
29. Platis, I. E., Ermácora, M. R., and Fox, R. O. (1993) Oxidative polypeptide cleavage mediated by EDTA-Fe covalently linked to cysteine residues. Biochemistry 32, 12761-12767.
30. Hoyer, D., Cho, H., and Schultz, P. G. (1990) A new strategy for selective protein cleavage. J. Am. Chem. Soc. 112, 3249-3250.
31. Ettner, N., Metzger, J. W., Lederer, T., Hulmers, J. D., Kisker, C., Hinrichs, W., Ellestad, G. A., and Hillen, W. (1995) Proximity mapping of the Tet repressor-tetracycline-Fe1 complex by hydrogen peroxide-mediated protein cleavage. Biochemistry 34, 22-31.
32. Parac, T. N., and Kostić, N. M. (1996) New selectivity and turnover in peptide hydrolysis by metal complexes. A palladium-(II) aqua complex catalyzes cleavage of peptides next to the histidine residue. J. Am. Chem. Soc. 118, 51-58.
33. Barefield, E. K. (1973) A new synthesis of 1,4,8,11-tetraazacy-clotetradecane (cyclam) via the Ni(II) complex. Inorg. Chem. 11, 2273-2274.
34. Schägger, H., and von Jagow, G. (1987) Tricine-sodium dodecyl sulfate-polyacrylamide gel electrophoresis for the separation of proteins in the range from 1 to 100 kDa. Anal. Biochem. 166, 368-379.
35. Aeschhach, R., Amadò, R., and Neukom, H. (1976) Formation of dityrosine cross-links in proteins by oxidation of tyrosine. Bio-chim. Biophys. Acta 439, 292-301.
36. Giulivi, C., and Davies, K. J. A. (1994) Dityrosine: a marker for oxidatively modified proteins and selective proteolysis. Methods Enzymol. 223, 363-371.
37. Malencik, D. A., and Anderson, S. R. (1991) Fluorometric characterization of dityrosine: Complex formation with boric acid and borate ion. Biophys. Biochem. Res. Commun. 178, 60-67.
38. Amadò, R., Aeschbach, R., and Neukom, H. (1984) Dityrosine: in vitro production and characterization. Methods Enzymol. 107, 377-388.
39. Stadtman, E. R. (1992) Protein oxidation and aging. Science 257, 1220-1224.
40. Stadtman, E. R. (1993) Oxidation of free amino acids and amino acid residues in proteins by radiolysis and by metal-catalyzed reactions. Annu. Rev. Biochem. 62, 797-821.
41. Marfey, P. S., Uziel, M., and Little, J. (1965) Reaction of bovine pancreatic ribonuclease A with 1,5-difluoro-2,4-dinitrobenzene. J. Biol. Chem. 240, 3270-3275.
42. Fry, S. C. (1984) Isodityrosine, a diphenyl ether cross-link in plant cell wall glycoprotein: identification, assay and chemical synthesis. Methods Enzymol. 107, 388-397.
43. Lee, J. E., Ciccarelli, R. B., and Jennette, K. W. (1982) Solubilization of the carcinogen nickel subsulfide and its interaction with deoxyribonucleic acid and protein. Biochemistry 21, 771-778.
44. Misra, M., Olinski, R., Dizdaroglu, M., and Kasprzak, K. S. (1993) Enhancement by L-histidine of nickel(II)-induced DNA-protein cross-linking and oxidative DNA base damage in the rat kidney. Chem. Res. Toxicol. 6, 33-37.
45. Zhuang, Z., Huang, X., and Costa, M. (1994) Protein oxidation and amino acid-DNA crosslinking by nickel compounds in intact cultured cells. Toxicol. Appl. Pharm. 126, 319-325.
46. Egan, W., Shindo, H., and Cohen, J. S. (1978) On the tyrosine residues of ribonuclease A. J. Biol. Chem. 253, 16-17.
47. Lenstra, J. A., Bolscher, B. G. J. M., Stob, S., Beintema, J. J., and Kaptein, R. ( 1979) The aromatic residues of bovine pancreatic ribonuclease studied by 1H nuclear magnetic resonance. Eur. J. Biochem. 98, 385-397.
48. Butler, J., Land, E. J., Priltz, W. A., and Swallow, A. J. (1986) Reversibility of charge transfer between tryptophan and tyrosine. J. Chem. Soc., Chem. Commun., 348-349.
49. Boguta, G., and Dancewicz, A. M. (1983) Radiolytic and enzymatic dimerization of tyrosyl residues in insulin, ribonuclease, papain and collagen. Int. J. Radiat. Biol. 43, 249-265.
50. Muller, J. G., Chen, X., Dadiz, A. C., Rokita, S. E., and Burrows, C. J. (1992) Ligand effects associated with the intrinsic selectivity of DNA oxidation promoted by nickel(II) macrocyclic complexes. J. Am. Chem. Soc. 114, 6407-6411.
51. Davies, K. J., and Delsignore, M. E. (1987) Protein damage and degradation by oxygen radicals. J. Biol. Chem. 262, 9908-9913.
52. Minisci, F., Citterio, A., and Giordano, C. (1983) Electron-transfer processes: Peroxydisulfate, a useful and versatile reagent in organic chemistry. Acc. Chem. Res. 16, 27-32.
53. Muller, J. G., Chen, X., Dadiz, A. C., Rokita, S. E., and Burrows, C. J. (1993) Macrocyclic nickel complexes in DNA recognition and oxidation. Pure Appl. Chem. 65, 545-550.
54. Bossu, F. P., and Margerum, D. W. (1977) Electrode potentials of nickel(III,II)-peptide complexes. Inorg. Chem. 16, 1210-1214.
55. Ball, D. L., and Edwards, J. O. (1958) The catalysis of the decomposition of Caro's Acid. J. Phys. Chem. 62, 343-345.
56. 2: Probing temperature-dependent conformations. J. Am. Chem. Soc. 118, 2320-232.
57. 2: Role of sulfate radical. Biochem. Biophys. Res. Commun. 176, 1306-1312.
58. Meunier, B. (1992) Potassium monopersulfate: Just another primary oxidant or a highly versatile oxygen atom donor in metalloporphyrin-mediated oxygenation and oxidation reactions. New J. Chem. 16, 203-211.
59. Coichev, N., and van Eldik, R. (1991) Kinetics and mechanism of the sulfite-induced autoxidation of cobalt(II) in aqueous azide medium. Inorg. Chem. 30, 2375-2380.
60. Brandt, C., and van Eldik, R. (1995) Transition metal-catalyzed oxidation of sulfur(IV) oxides. Atmospheric-relevant processes and mechanisms. Chem. Rev. 95, 119-190.
61. Muller, J. G., Hickerson, R. P., Perez, R. J., and Burrows, C. J. (1997) DNA damage from sulfite autoxidation catalyzed by a nickel(II) peptide. J. Am. Chem. Soc. 119, 1501-1506.
62. Predki, P. F., Harford, C., Brar, P., and Sarkar, B. ( 1992) Further characterization of the N-terminal copper(II)- and nickeK (II)-binding motifs of proteins. Biochem. J. 287, 211-215.
63. 2, a putative metal binding sequence of histone H3. Chem. Res. Toxicol. 8, 683-692.
64. Breslow, E., and Girottie, A. W. (1966) The interaction of ribonuclease with metal ions, I. J. Biol. Chem. 241, 5651-5660.
65. Girotti, A. W., and Breslow, E. (1968) The interaction of ribonuclease with metal ions, II. J. Biol. Chem. 243, 216-218.
66. Walters, D. E., and Allerhand, A. (1980) Tautomeric states of the histidine residues of bovine pancreatic ribonuclease A. J. Biol. Chem. 255, 6200-6204.
67. Howarth, O. W., and Lian, L. Y. (1984) Ribonuclease A: Carbon-13 nuclear magnetic resonance assignments, binding sites, and conformational flexibility. Biochemistry 23, 3515-3521.
68. Blackburn, P., and Moore, S. (1982) Pancreatic ribonuclease. Enzymes 15, 317-433.
69. Sosnick, T. R., and Trewhella, J. (1992) Denatured states of ribonuclease A have compact dimensions and residual secondary structure. Biochemistry 31, 8329-8335.
70. Tilton, R. F., Jr., Dewan, J. C., and Petsko, G. A. (1992) Effects of temperature on protein structure and dynamics: X-ray crystal-lographic studies of the protein ribonuclease A at nine different temperatures from 98 to 320 K. Biochemistry 31, 2469-2481.