Modeling the reduction of hydrogen peroxide by glutathione peroxidase mimics

Journal of Physical Chemistry A

Volumn 110, Issue 28, 2006, Pages 8979-8985

  Pearson, Jason K ^a   Boyd, Russell J ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIOXIDANTS; CHEMICAL REACTIONS; MATHEMATICAL MODELS; QUANTUM THEORY; REDOX REACTIONS; SULFUR;

EBSELEN DISELENIDE MODELS; EBSELEN SELENOL; GLUTATHIONE PEROXIDASE MIMICS;

HYDROGEN PEROXIDE;

2 SELENYLBENZANILIDE; 2-SELENYLBENZANILIDE; ANILIDE; BENZAMIDE DERIVATIVE; BIS(2 (N PHENYLCARBOXAMIDO)PHENYL)DISELENIDE; BIS(2-(N-PHENYLCARBOXAMIDO)PHENYL)DISELENIDE; EBSELEN; GLUTATHIONE PEROXIDASE; HYDROGEN PEROXIDE; ORGANOSELENIUM DERIVATIVE; PYRROLE DERIVATIVE; SULFUR;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; OXIDATION REDUCTION REACTION;

ANILIDES; AZOLES; BENZAMIDES; GLUTATHIONE PEROXIDASE; HYDROGEN PEROXIDE; KINETICS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORGANOSELENIUM COMPOUNDS; OXIDATION-REDUCTION; SULFUR;

EID: 33747015364     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0615196     Document Type: Article

References (65)

1. Flohé, L.; Loschen, G.; Günzler, W. A.; Eichele, E. Hoppe-Seyler's Z. Physiol. Chem. 1972, 353, 987.
2. Selenium in Biology and Human Health; Burk, R. F., Ed.; Springer-Verlag: New York, 1994.
3. Flohé, L. Curr. Top. Cell. Regul. 1985, 27, 473.
4. Tappel, A. L. Curr. Top. Cell. Regul. 1984, 24, 87.
5. Epp, O.; Ladenstein, R.; Wendel, A. Eur. J. Biochem. 1983, 133, 51.
6. Free Radicals in Biology; Pryor, W. A., Ed.; Academic Press: New York, 1976-1982; Vols. 1-5.
7. Free Radicals in Molecular Biology, Aging and Disease; Armstrong, D., Sohal, R. S., Cutler, R. G., Slater, T. F., Eds.; Raven Press: New York, 1984.
8. Ganther, H. E. Chem. Scr. 1975, 8a, 79.
9. Ganther, H. E.; Kraus, R. J. In Methods in Enzymology; Colowick, S. P., Kaplan, N. O., Eds.; Academic Press: New York, 1984; Vol. 107, pp 593-602.
10. Stadtman, T. C. J. Biol. Chem. 1991, 266, 16257.
11. Aumann, K. D.; Bedorf, N.; Brigelius-Flohé, R.; Schomburg, D.; Folhé, L. BES 1997, 10, 136.
12. Flohé, L. In Glutathione: Chemical, Biochemical and Medical Aspects; Dolphin, D., Poulson, R., Avramovic, O., Eds.; John Wiley & Sons: New York, 1989; pp 643-731.
13. Benkova, Z.; Kóňa, J.; Gann, G.; Fabian, W. M. F. Int. J. Quantum Chem. 2002, 90, 555.
14. Mugesh, G.; Panda, A.; Singh, H. B.; Punekar, N. S.; Butcher, R. J. J. Am. Chem. Soc. 2001, 123, 839.
15. Bailly, F.; Azaroual, N.; Bernier, J. L. Bioorg. Med. Chem. 2003, 11, 4623.
16. Back, T. G.; Moussa, Z. J. Am. Chem. Soc. 2003, 125, 13455-13460.
17. Mugesh, G.; Du Mont, W. W. Chem.-Eur. J. 2001, 7, 1365.
18. Mugesh, G.; Singh, H. B. Chem. Soc. Rev. 2000, 29, 347.
19. Wirth, T. Molecules 1998, 3, 164.
20. Wilson, S. R.; Zucker, P. A.; Huang, R.-R. C.; Spector, A. J. Am. Chem. Soc. 1989, 111, 5936.
21. Reich, H. J.; Jasperse, C. P. J. Am. Chem. Soc. 1987, 109, 5549.
22. Iwaoka, M.; Tomoda, S. J. Am. Chem. Soc. 1996, 118, 8077.
23. Mugesh, G.; Panda, A.; Singh, H. B.; Punekar, N. S.; Butcher, R. J. J. Chem. Soc., Chem. Commun. 1998, 2227.
24. Galet, V.; Bernier, J. L.; Heniehart, J. P.; Lesieur, D.; Abadie, C.; Rochelte, L.; Lindenbaum, A.; Chalas, J.; Renaud de la Faverie, J. F.; Pfeiffer, B.; Renard, P. J. Med. Chem. 1994, 37, 2903.
25. Iwaoka, M.; Tomoda, S. J. Am. Chem. Soc. 1994, 116, 2557.
26. Müller, A.; Cadenas, E.; Graf, P.; Sies, H. Biochem. Pharmacol. 1984, 33, 3235.
27. Wendel, A.; Fausel, M.; Safayhi, H.; Tiegs, G.; Otter, R. Biochem. Pharmacol. 1984, 33, 3241.
28. Parnham, M. J.; Kindt, S. Biochem. Pharmacol. 1984, 33, 3247.
29. Müller, A.; Gabriel, H.; Sies, H. Biochem. Pharmacol. 1985, 34, 1185.
30. Safayhi, H.; Tiegs, G.; Wendel, A. Biochem. Pharmacol. 1985, 34, 2691.
31. Wendel, A.; Tiegs, G. Biochem. Pharmacol. 1986, 35, 2115.
32. Zhao, R.; Masayasu, H.; Holmgren, A. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 8579.
33. Wendel, A.; Fausel, M.; Safayhi, H.; Tiegs, G.; Otter, R. Biochem. Pharmacol. 1984, 33, 3241.
34. Müller, A.; Cadenas, E.; Graf, P.; Sies, H. Biochem. Pharmacol. 1984, 33, 3235.
35. Parnham, M. J.; Kindt, S. Biochem. Pharmacol. 1984, 33, 3247.
36. Fong, M. C.; Schiesser, C. H. Tetrahedron Lett. 1995, 36, 7329.
37. Sies, H. Free Radical Biol. Med. 1993, 14, 313.
38. Sies, H. Methods Enzymol. 1994, 234, 476.
39. Schewe, T. Gen. Pharmacol. 1995, 26, 1153.
40. Nakamura, Y.; Feng, Q.; Kumagi, T.; Torikai, K.; Ohigashi, H.; Osawa, T.; Noguchi, N.; Niki, E.; Uchida, K. J. Biol. Chem. 2002, 277, 2687.
41. Zhang, M.; Nomura, A.; Uchida, Y.; Iijima, H.; Sakamoto, T.; Iishii, Y.; Morishima, Y.; Mochizuki, M.; Masuyama, K.; Hirano, K.; Sekizawa, K. Free Radical Biol. 2002, 32, 454.
42. Fischer, H.; Terlinden, R.; Lohr, J. P.; Romer, A. Xenobiotica 1988, 18, 1347.
43. Müller, A.; Gabriel, H.; Sies, H.; Terlinden, R.; Fischer, H.; Romer, A. Biochem. Pharmacol. 1988, 37, 1103.
44. Sies, H. In Selenium in Biology and Medicine; Wendel, A., Ed.; Springer-Verlag: Heidelberg, 1989; pp 153-162.
45. Zhao, R.; Holmgren, A. J. Biol Chem. 2002, 277, 39456.
46. Engman, L.; Stern, D.; Cotgreave, I. A.; Andersson, C. M. J. Am. Chem. Soc. 1992, 114, 9737.
47. Fischer, H.; Dereu, N. Bull. Soc. Chim. Belg. 1987, 96, 757.
48. Haenen, G. R. M. M.; De Rooij, B. M.; Vermeulen, N. P. E.; Bast, E. Mol. Pharmacol. 1990, 37, 412.
49. Glass, R. S.; Farooqui, F.; Sabahi, M.; Ehler, K. W. J. Org. Chem. 1989, 54, 1092.
50. Back, T. G.; Moussa, Z. J. Am. Chem. Soc. 2003, 125, 13455.
51. Pearson, J. K.; Ban, F.; Boyd, R. J. J. Phys. Chem. 2005, 109, 10373.
52. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Kiene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.
53. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
54. Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 45, 13244.
55. Peng, C.; Schlegel, H. B. Isr. J. Chem. 1993, 33, 449.
56. Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49.
57. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
58. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.
59. Biegler-König, F. W.; Schönbohm, J.; Bayles, D. J. Comput. Chem. 2001, 22, 545.
60. Biegler-König, F. W.; Schönbohm, J.; Bayles, D. The AIM2000 program can be downloaded from the Internet at http://gauss.fh-bielefeld.de/ aim2000.
61. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: Oxford, U.K., 1990.
62. Castillo, N.; Matta, C. F.; Boyd, R. J. Chem. Phys. Lett. 2005, 409, 265.
63. Sarma, B. K.; Mugesh, G. J. Am. Chem. Soc. 2005, 127, 11477.
64. Kice, J. L.; Chiou, S. J. Org. Chem. 1986, 51, 290.
65. Zhang, X.; Xu, H.; Dong, Z.; Wang, Y.; Liu, J.; Shen, J. J. Am. Chem. Soc. 2004, 126, 10556.