Comparison of Thioethers and Sulfoxides as Axial Ligands for N-Acetylmicroperoxidase-8: Implications for Oxidation of Methionine-80 in Cytochrome c

Inorganic Chemistry

Volumn 42, Issue 23, 2003, Pages 7550-7559

  Lushington, Gerald H ^a   Cowley, Aaron B ^a   Silchenko, Svetlana ^a   Lukat Rodgers, Gudrun S ^b   Rodgers, Kenton R ^b   Benson, David R ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (METHYLTHIO)ETHANOL; CYTOCHROME C; DIMETHYL SULFOXIDE; HEME; IRON; IRON COMPLEX; METHIONINE; N ACETYLMICROPEROXIDASE 8; PEROXIDASE; REACTIVE OXYGEN METABOLITE; SULFIDE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CALCULATION; COMPARATIVE STUDY; COMPLEX FORMATION; ENTHALPY; MOLECULAR INTERACTION; MOLECULAR STABILITY; OXIDATION; QUANTUM CHEMISTRY; RAMAN SPECTROMETRY; STEREOSPECIFICITY;

ANIMALS; CHOLINE; CYTOCHROMES C; DIMETHYL SULFOXIDE; FERRIC COMPOUNDS; FERROUS COMPOUNDS; HEMEPROTEINS; HORSES; LIGANDS; METHIONINE; MODELS, MOLECULAR; MYOCARDIUM; OXIDATION-REDUCTION; PEPTIDE FRAGMENTS; SPECTROPHOTOMETRY; SPECTRUM ANALYSIS, RAMAN; THERMODYNAMICS;

EID: 0242693440     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic034689v     Document Type: Article

References (77)

1. Gilbert, D. L., Colton, C. A., Eds. Reactive Oxygen Species in Biological Systems; Kluwer Academic/Plenum: New York, 1999.
2. Stadtman, E. R. Annu. Rev. Biochem. 1993, 62, 797-821.
3. Berlett, B. S.; Stadtman, E. R. J. Biol. Chem. 1997, 272, 20313-20316.
4. Brot, N.; Weissbach, H. Arch. Biochem. Biophys. 1983, 223, 271-281.
5. Vogt, W. Free Radical Biol. Med. 1995, 18, 93-105.
6. Moore, G. R.; Pettigrew, G. W. Cytochromes c. Evolutionary, structural and physicochemical aspects; Springer-Verlag: Berlin, 1990.
7. Pettigrew, G. W.; Moore, G. R. Cytochromes c. Biological aspects; Springer-Verlag: Berlin, 1987.
8. Finkel, T.; Holbrook, N. J. Nature 2000, 408, 239-247.
9. Sbarra, A. J., Strauss, R. R., Eds. The Respiratory Burst and its Physiological Relevance; Plenum Press: New York, 1988.
10. Zgliczynski, J. M.; Stelmaszynska, T. In The Respiratory Burst and Its Physiological Mechanism: Sbarra, A. J., Strauss, R. R., Eds.; Plenum: New York, 1988; pp 315-347.
11. Dunford, H. B. Heme Peroxidases; Wiley-VCH: New York, 1999; pp 349-378.
12. Albrich, J. M.; McCarthy, C. A.; Hurst, J. K. Proc. Natl. Acad. Sci., U.S.A. 1981. 78, 210-214.
13. Bernofsky, C. FASEB J. 1991, 5, 295-300.
14. Hurst, J. K., Jr.; Barrette, W. C., Jr. Crit. Rev. Biochem. Mol. Biol. 1989, 24, 271-328.
15. Prütz, W. A.; Kissner, R.; Nauser, T.; Koppenol, W. H. Arch. Biochem. Biophys. 2001, 389, 110-122.
16. Heinecke, J. W. FASEB J. 1999, 13, 1113-1120.
17. Chen, Y.-R.; Deterdling, L. J.; Sturgeon, B. E.; Tomer, K. B.; Mason, R. P. J. Biol. Chem. 2002, 277, 0000.
18. Ivanetich, K. M.; Bradshaw, J. J.; Kaminsky, J. S. Biochemistry 1976, 15, 1144-1153.
19. Ivanetich, K. M.; Bradshaw, J. J.; Fazakerley, G. V. Biochem. Biophys. Res. Commun. 1976, 72, 433-439.
20. Brittain, T.; Greenwood, C. Biochem. J. 1976, 159, 621-626.
21. Feinberg, B. A.; Bedore, J. E., Jr.; Ferguson-Miller, S. Biochim. Biophys. Acta 1986, 851, 157-165.
22. Pande, J.; Kinnally, K.; Thallum, K. K.; Verma, B. C.; Myer, Y. P.; Rechsteiner, L.; Bosshard, H. R. J. Protein Chem. 1987, 6, 295-319.
23. Myer, Y. P.; Kumar, S.; Kinnally, K.; Pande, J. J. Protein Chem. 1987, 6, 321-342.
24. Wallace, C. J. A.; Clark-Lewis, I. J. Biol. Chem. 1992, 267, 3852-3861.
25. Larsen, R. W. Biochim. Biophys. Acta 2003, 1619, 15-22.
26. George, P.; Schejter, A. J. Biol. Chem. 1964, 239, 1504-1508.
27. Babul, J.; Stellwagen, E. Biochemistry 1972, 11, 1195-1200.
28. Harbury, H. A.; Loach, P. A. J. Biol. Chem. 1960, 235, 3640-3645.
29. Adams, P. A.; Baldwin, D. A.; Marques, H. M. In Cytochrome c. A Multidisciplinary Approach; Scott, R. A., Mauk, A. G., Eds.; University Science Books: Sausalito, CA, 1996; Chapter 20.
30. Yang, E. K.; Sauer, K. In Electron Transport and Oxygen Utilization; Ho, C., Ed.; Elsevier: Amsterdam, The Netherlands, 1982; p 82.
31. Wang, J.-S.; Van Wart, H. E. J. Phys. Chem. 1989, 93, 7925-7931.
32. Low, D. P.; Winkler, J. R.; Gray, H. B. J. Am. Chem. Soc. 1996, 118, 117-120.
33. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S., Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. V.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 1998.
34. Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724-728.
35. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261.
36. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654-3665.
37. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
38. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
39. Sharma, C. V. K.; Broker, G. A.; Huddleston, J. G.; Baldwin, J. W.; Metzger, R. M.; Rogers, R. D. J. Am. Chem. Soc. 1999, 121, 1137-1144.
40. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
41. Boys, S. F. Rev. Mod. Phys. 1960, 32, 296-299.
42. Perdoncin, G.; Scorranto, G. J. Am. Chem. Soc. 1977, 99, 6983-6986.
43. Pearson, R. G. J. Chem. Educ. 1968, 45, 581-643.
44. Harbury, H. A.; Cronin, J. R.; Fanger, M. W.; Hettinger, T. P.; Murphy, A. J.; Myer, Y. P.; Vinogradov, S. N. Proc. Natl. Acad. Sci. U.S.A. 1965, 54, 1658-1664.
45. Margoliash, E.; Schejter, A. Adv. Protein Chem. 1966, 21, 113-283.
46. Schejter, A. In Cytochrome c: A multidisciplinary approach: Scott, R. A., Mauk, A. G., Eds.; University Science Books: Sausalito, CA, 1996; Chapter 8.
47. Tezcan, F. A.; Winkler, J. R.; Gray, H. B. J. Am. Chem. Soc. 1998, 120, 13383-13388.
48. Xu, Y.; Mayne, L.; Englander, S. W. Nature Struct. Biol. 1998, 5, 774-778.
49. Davies, J. A. Adv. Inorg. Chem. Radiochem. 1981, 24, 115-187.
50. Calligaris, M.; Carugo, O. Coord. Chem. Rev. 1996, 153, 83-154.
51. Aron, J.; Baldwin, D. A.; Marques, H. M.; Pratt, J. M.; Adams, P. A. J. Inorg. Biochem. 1986, 27, 227-243.
52. Othman, S.; Le Lirzin, A.; Desbois, A. Biochemistry 1994, 33, 15437-15448.
53. Munro, O. Q.; Marques, H. M. Inorg. Chem. 1996, 35, 3752-3767.
54. Lu, Y.; Casimiro, D. R.; Bren, K. L.; Richards, J. H.; Gray, H. B. Proc. Natl. Acad. Sci., U.S.A. 1993, 90, 11456-11459.
55. Banci, L.; Bertini, I.; Bren, K. L.; Gray, H. B.; Turano, P. Chem. Biol. 1995, 2, 377-383.
56. Othman, S.; Le Lirzin, A.; Desbois, A. Biochemistry 1993, 32, 9781-9791.
57. Turucek, F. J. Phys. Chem. A 1998, 102, 4703-4713.
58. Rasul, G.; Prakash, G. K. S.; Olah, G. A. J. Org. Chem. 2000, 65, 8786-8789.
59. Mashiko, T.; Kastner, M. E.; Spartalian, K.; Scheidt, W. R.; Reed, C. A. J. Am. Chem. Soc. 1978, 100, 6354-6362.
60. Mylrajan, M.; Andersson, L. A.; Sun, J.; Loehr, T. M.; Thomas, C. S.; Sullivan, E. P.; Thomson, M. A.; Long, K. M.; Anderson, O. P.; Strauss, S. H. Inorg. Chem. 1995, 34, 3953-3963.
61. Kadish, K. M.; Cornillon, J.-L.; Mitaine, P.; Deng, Y. J.; Korp, D. J. Inorg. Chem. 1989, 28, 2534-2542.
62. Pacheco, A.; James, B. R.; Rettig, S. J. Inorg. Chem. 1999, 38, 5579-5587.
63. Calderazzo, F.; Pampaloni, G.; Vitali, D.; Collamati, I.; Dessy, G.; Fares, V. J. Chem. Soc., Dalton Trans. 1980, 1965-1969.
64. Küppers, J.-J.; Wieghardt, K.; Nuber, B.; Weiss, J.; Bill, E.; Trautwein, A. X. Inorg. Chem. 1987, 26, 3762-3769.
65. Carini, C.; Pelizzi, C.; Pelizzi, G.; Predieri, G.; Tarasconi, P.; Vitali, F. J. Chem. Soc., Chem. Commun. 1990, 613-614.
66. Rovira, C.; Carloni, P.; Parrinello, M. J. Phys. Chem. B 1999, 103, 7031-7035.
67. Mashiko, T.; Reed, C. A.; Haller, K. A.; Kastner, M. E.; Scheidt, W. R. J. Am. Chem. Soc. 1981, 103, 5758-5767.
68. Schejter, A.; Plotkin, B. Biochem. J. 1988, 255, 353-356.
69. Rack, J. J.; Gray, H. B. Inorg. Chem. 1999, 38, 2-3.
70. Pacheco, A.; James, B. R.; Rettig, S. J. Inorg. Chem. 1995, 34, 3477-3484.
71. Spiro, T. G.; Strekas, T. C. J. Am. Chem. Soc. 1974, 96, 338-345.
72. Cartling, B. Biophys. J. 1983, 43, 191-205.
73. Spiro, T. G.; Burke, J. M. J. Am. Chem. Soc. 1976, 98, 5482-5489.
74. Larsen, R. W.; Murphy, J.; Findsen, E. W. Inorg. Chem. 1996, 35, 6254-6260.
75. Rablen, P. R.; Lockman, J. W.; Jorgensen, W. L. J. Phys. Chem. A 1998, 102, 3782-3797.
76. Lowther, W. T.; Brot, N.; Weissbach, H.; Matthews, B. W. Biochemistry 2000, 39, 13307-13312.
77. Grimaud, R.; Ezraty, B.; Mitchell, J. K.; Lafitte, D.; Briand, C.; Derrick, P. J.; Barras, F. J. Biol. Chem. 2001, 276, 48915-48920.