A synthetic model for the inhibition of glutathione peroxidase by antiarthritic gold compounds

Inorganic Chemistry

Volumn 48, Issue 6, 2009, Pages 2449-2455

  Bhabak, Krishna P ^a   Mugesh, Govindasamy ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

GLUTATHIONE PEROXIDASE; GOLD DERIVATIVE; ORGANOSELENIUM DERIVATIVE;

ARTHRITIS; ARTICLE; BIOLOGICAL MODEL; BIOMIMETICS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; HUMAN; METABOLISM; SYNTHESIS;

ARTHRITIS; BIOMIMETICS; GLUTATHIONE PEROXIDASE; GOLD COMPOUNDS; HUMANS; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; ORGANOSELENIUM COMPOUNDS;

EID: 64349106780     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic8019183     Document Type: Article

References (48)

1. (a) Brown, D. H.; Smith, W. E. Chem. Soc. Rev. 1980, 9, 217-240.
2. (b) Flicker, S. P. Gold Bull. 1996, 29, 53-59.
3. (c) Shaw, C. F., III. Chem. Rev. 1999, 99, 2589-2600.
4. (d) Tiekink, E. R. T. Crit. Rev. Oncol/Hematol. 2002, 42, 225-248.
5. (a) Hashimoto, K.; Whitehurst, C. E.; Matsubara, T.; Hirohata, K.; Lipsky, P. E. J. Clin. Invest. 1992, 89, 1839-1848, and references cited therein.
6. (b) McKeage, M. I.; Maharaj, L.; Berners-Price, S. I. Coord. Chem. Rev. 2002, 232, 127-135.
7. (a) Chaudiere, I.; Tappel, A. L. J. Inorg. Biochem. 1984, 20, 313-325.
8. (b) Baker, M. A.; Tappel, A. L. Biochem. Pharmacol. 1986, 35, 2417-2422.
9. (c) Roberts, I. R.; Shaw, C. F., III. Biochem. Pharmacol. 1998, 55, 1291-1299.
10. (d) Ren, B.; Huang, W.; Åkesson, B.; Laden-stein, R. J. Mol. Biol. 1997, 268, 869-885.
11. Berry, M. J.; Kieffer, J. D.; Harney, J. W.; Larsen, P. R. J. Biol. Chem. 1991, 266, 14155-14158.
12. (a) Smith, A. D.; Guidry, C. A.; Morris, V. C; Levander, O. A. Nutr. Requir. Interact. 1998, 194-198.
13. (b) Gromer, S.; Arscott, L. D.; Williams, C. H., Jr.; Schirmer, R. H.; Becker, K. J. Biol. Chem. 1998. 273, 20096-20101.
14. (a) Flohé, L.; Günzler, E. A.; Schock, H. H. FEBS Lett. 1973, 32. 132-134.
15. (b) Rotruck, J. T.; Pope, A. L.; Ganther, H. E.; Swanson. A. B.; Hafeman, D. G.; Hoekstra, W. G. Science 1973, 179, 588-590.
16. (c) Mugesh, G.; Singh, H. B. Chem. Soc. Rev. 2000, 29, 347-357.
17. (a) Wilson, S. R.; Zucker, P. A.; Huang, R.-R. C; Spector, A. J. Am. Chem. Soc. 1989, 111, 5936-5939.
18. (b) Mugesh, G.; du Mont, W.-W. Chem-Eur. J. 2001, 7, 1365-1370.
19. (c) Jacob, C; Giles, G. I.; Giles. N. M.; Sies, H. Angew. Chem., Int. Ed. 2003, 42, 4742-4758.
20. (d) Roy. G.; Sarma, B. K.; Phadnis, P. P.; Mugesh, G. J. Chem. Sci. 2005, 117, 287-303.
21. (e) Prabhakar, R.; Vreven, T.; Morokuma, K.; Musaev. D. G. Biochemistry 2005, 44, 11864-11871.
22. (f) Prabhakar, R.; Morokuma, K.; Musaev, D. G. Biochemistry 2006, 45, 6967-6977.
23. (a) Deponte, M.; Urig, S.; Arscott, L. D.; Fritz-Wolf, K.; Réau, R.; Herold-Mende, C; Koncarevic, S.; Meyer, M.; Davioud-Charvet, E.: Ballon, D. P.; Williams, C. H., Jr.; Becker, K. J. Biol. Chem. 2005. 280, 20625-20637.
24. (b) Urig, S.; Fritz-Wolf, K.; Réau, R.; Herold-Mende, C; Tóth, K.; Davioud-Charvet, E.; Becker, K. Angew. Chem., Int. Ed. 2006, 45, 1881-1886.
25. (a) Iwaoka, M.; Tomoda, S. J. Am. Chem. Soc. 1994, 116, 2557-2561.
26. (b) Mugesh, G.; Panda, A.; Singh, H. B.; Punekar, N. S.: Butcher, R. J. J. Am. Chem. Soc. 2001, 123, 839-850.
27. (c) Bhabak. K. P.; Mugesh, G. Chem.-Eur. J. 2008, 14, 8640-8651.
28. (a) Back, T. G.; Moussa, Z. J. Am. Chem. Soc. 2002, 124, 12104-12105.
29. (b) Back, T. G.; Moussa, Z.; Parvez, M. Angew. Chem., Int. Ed. 2004, 43, 1268-1270.
30. (c) Sarma, B. K.; Mugesh, G. J. Am. Chem. Soc. 2005, 127, 11477-11485.
31. (d) Bhabak, K. P.; Mugesh, G. Chem-Eur. J. 2007, 13, 4594-4601.
32. (a) Kaur, R.; Singh, H. B.; Patel, R. P. J. Chem. Soc, Dalton Trans. 1996, 2719-2726.
33. (b) Panda, A.; Mugesh, G.; Singh, H. B.; Butcher, R. J. Organometallics 1999, 18, 1986-1993.
34. 31P NMR chemical shifts observed for trialkyl/ arylphosphinegold selenolate complexes 11-13 are comparable with that of the triph-enylphosphinegold(I) complex (36.8 ppm) derived from o-carborane. Canales, S.; Crespo, O.; Gimeno, M. C; Jones, P. G.; Laguna, A.: Romero, P. Dalton Trans. 2003, 4525-4528.
35. N-Boc-L-selenocysteine methyl ester was synthesized by the following literature method. (a) Bhat, R. G.; Porhiel, E.; Saravanan, V.; Chandrasekaran, S. Tetrahedron Lett. 2003, 44, 5251-5253.
36. (b) Phadnis, P. P.; Mugesh, G. Org. Biomol. Chem. 2005, 3, 2476-2481.
37. (a) Coffer, M. T.; Shaw, C. F., III.; Hormann, A. L.; Mirabelli, C. K.: Crooke, S. T. J. Inorg. Biochem. 1987, 30, 177-187.
38. (b) Shaw, C. F., III.; Isab, A. A.; Hoeschele, J. D.; Starich, M.; Locke, J.; Schulteis. P.; Xiao, J. J. Am. Chem. Soc. 1994, 116, 2254-2260.
39. (c) Roberts, J. R.; Xiao, J.; Schliesman, B.; Parsons, D. J.; Shaw, C. F., III. Inorg. Chem. 1996, 35, 424-433.
40. 3 was unchanged upon the addition of even a large excess (10 equiv) of PhSH. Similar results were obtained when the experiments were carried out in MeOH. Furthermore, the phosphine ligand displacement by PhSH was not observed after the formation of gold selenolate complexes (11-13), suggesting that the gold selenolate complexes having a Se-Au-P moiety can be obtained in the presence of thiols. Ahhmad, S.; Isab, A. A. J. Inorg. Biochem. 2002, 88, 44-52.
41. (a) Jones, P. G.; Thöne, C. Inorg. Chim. Acta 1991, 181, 291-294.
42. (b) Baker, M. V.; Barnard, P. J.; Berners-Price, S. J.; Brayshaw, S. K.: Hickey, J. L.; Skelton, B. W.; White, A. H. Dalton Trans. 2006, 3708-3715.
43. (c) Hickey, J. M.; Ruhayel, R. A.; Barnerd, P. J.; Baker, M. V.; Berners-Price, S. J.; Filipovska, A. J. Am. Chem. Soc. 2008, 130. 12570-12571.
44. Bowmaker, G. A.; Dyason, J. C; Healy, P. C; Engelhardt, L. M.; Pakawatchai, C; White, A. H. J. Chem. Soc, Dalton Trans. 1987. 1089-1097.
45. (a) Guy, J. J.; Jones, P. G.; Sheldrick, G. M. Acta Crystallogr. 1976. B32, 1937-1938.
46. (b) Mays, M. J.; Vergnano, P. A. J. Chem. Soc, Dalton Trans. 1979, 1112-1115.
47. (c) Staples, R. J.; King, C; Khan, M. N. I.; Winpenny, R. E. P.; Fackler, J. P., Jr. Acta Crystallogr. 1993, C49, 472-475.
48. (d) Wang, J.-C. Acta Crystallogr. 1996, C52. 611-613.