Functional mimics of glutathione peroxidase: Bioinspired synthetic antioxidants

Accounts of Chemical Research

Volumn 43, Issue 11, 2010, Pages 1408-1419

  Bhabak, Krishna P ^a   Mugesh, Govindasamy ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE; ANTIOXIDANT; GLUTATHIONE PEROXIDASE; ORGANOSELENIUM DERIVATIVE;

ARTICLE; BIOCATALYSIS; CHEMISTRY; ENZYME ACTIVE SITE; METABOLISM; MOLECULAR MIMICRY; SYNTHESIS;

AMIDES; AMINES; ANTIOXIDANTS; BIOCATALYSIS; CATALYTIC DOMAIN; GLUTATHIONE PEROXIDASE; MOLECULAR MIMICRY; ORGANOSELENIUM COMPOUNDS;

EID: 78649287952     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar100059g     Document Type: Article

References (65)

1. Flohé, L.; Günzler, E. A.; Schock, H. H. Glutathione peroxidase- selenoenzyme FEBS Lett. 1973, 32, 132-134
2. Rotruck, J. T.; Pope, A. L.; Ganther, H. E.; Swanson, A. B.; Hafeman, D. G.; Hoekstra, W. G. Selenium-biochemical roles as a component of glutathione peroxidase Science 1973, 179, 588-590
3. Behne, D.; Kyriakopoulos, A.; Meinhold, H.; Köhrle, J. Identification of type-I iodothyronine 5′-deiodinase as a selenoenzyme Biochem. Biophys. Res. Commun. 1990, 173, 1143-1149
4. Köhrle, J. Iodothyronine deiodinases Methods Enzymol. 2002, 347, 125-167
5. Tamura, T.; Stadtman, T. C. A new selenoprotein from human lung adenocarcinoma cells: purification, properties, and thioredoxin reductase activity Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 1006-1011
6. Flohé, L. Glutathione peroxidase brought into focus. In Free radicals in biology; Pryor, W. A., Ed.; Academic Press: New York, 1982, Vol. 5; pp 223 - 253.
7. Arnér, E. S. J.; Holmgren, A. Physiological functions of thioredoxin and thioredoxin reductase Eur. J. Biochem. 2000, 267, 6102-6109
8. For a review, see
9. Sarma, B. K.; Mugesh, G. Thiol cofactors for selenoenzymes and their synthetic mimics Org. Biomol. Chem. 2008, 6, 965-974
10. Brandt, W.; Wessjohann, L. A. The functional role of selenocysteine (Sec) in the catalysis mechanism of large thioredoxin reductases: proposition of a swapping catalytic triad including a Sec-His-Glu state ChemBioChem 2005, 6, 386-394
11. Gromer, S.; Wessjohann, L. A.; Eubel, J.; Brandt, W. Mutational studies confirm the catalytic triad in the human selenoenzyme thioredoxin reductase predicted by molecular modeling ChemBioChem 2006, 7, 1649-1652
12. Wessjohann, L. A.; Schneider, A.; Abbas, M.; Brandt, W. Selenium in chemistry and biochemistry in comparison to sulfur Biol. Chem. 2007, 388, 997-1006
13. Lacey, B. M.; Eckenroth, B. E.; Flemer, S, Jr.; Hondal, R. J. Selenium in thioredoxin reductase: a mechanistic perspective Biochemistry 2008, 47, 12810-12821
14. Wessjohann, L. A.; Schneider, A. Synthesis of selenocysteine and its derivatives with an emphasis on selenenylsulfide (-Se-S-) formation Chem. Biodiversity 2008, 5, 375-388
15. Ursini, F.; Maiorino, M.; Brigelius-Flohé, R.; Aumann, K.-D.; Roveri, A.; Schomburg, D.; Flohé, L. Diversity of glutathione peroxidases Methods Enzymol. 1995, 252, 38-53
16. Epp, O.; Ladenstein, R.; Wendel, A. The refined structure of the selenoenzyme glutathione peroxidase at 0.2-nm resolution Eur. J. Biochem. 1983, 133, 51-69
17. Ren, B.; Huang, W.; Åkesson, B.; Ladenstein, R. The crystal structure of seleno-glutathione peroxidase from human plasma at 2.9 Å resolution J. Mol. Biol. 1997, 268, 869-885
18. Syed, R.; Wu, Z.-P.; Hogle, J. M.; Hilvert, D. Crystal structure of selenosubtilisin at 2.0 Å Resolution Biochemistry 1993, 32, 6157-6164
19. Mugesh, G.; Singh, H. B. Synthetic organoselenium compounds as antioxidants: glutathione peroxidase activity Chem. Soc. Rev. 2000, 29, 347-357
20. Mugesh, G.; du Mont, W.-W.; Sies, H. The chemistry of biologically important synthetic organoselenium compounds Chem. Rev. 2001, 101, 2125-2179
21. Müller, A.; Cadenas, E.; Graf, P.; Sies, H. A novel biologically active seleno-organic compound-1: glutathione peroxidase-like activity in vitro and antioxidant capacity of PZ-51 (Ebselen) Biochem. Pharmacol. 1984, 33, 3235-3239
22. Wendel, A.; Fausel, M.; Safayhi, H.; Tiegs, G.; Otter, R. A novel biologically active seleno-organic compound-II: activity of PZ-51 in relation to glutathione peroxidase Biochem. Pharmacol. 1984, 33, 3241-3245
23. Schewe, T. Molecular actions of Ebselen-an antiinflammatory antioxidant Gen. Pharmacol. 1995, 26, 1153-1169
24. Back, T. G.; Dyck, B. P. A novel camphor-derived selenenamide that acts as a glutathione peroxidase mimetic J. Am. Chem. Soc. 1997, 119, 2079-2083
25. Wilson, S. R.; Zucker, P. A.; Huang, R.-R. C.; Spector, A. Development of synthetic compounds with glutathione peroxidase activity J. Am. Chem. Soc. 1989, 111, 5936-5939
26. Iwaoka, M.; Tomoda, S. A model study on the effect of an amino group on the antioxidant activity of glutathione peroxidase J. Am. Chem. Soc. 1994, 116, 2557-2561
27. Alberto, E. E.; Soares, L. C.; Sudati, J. H.; Borges, A. C. A.; Rocha, J. B. T.; Braga, A. L. Efficient synthesis of modular amino acid derivatives containing selenium with pronounced GPx-like activity Eur. J. Org. Chem. 2009, 4211-4214
28. Mishra, B.; Priyadarsini, K. I.; Mohan, H.; Mugesh, G. Horseradish peroxidase inhibition and antioxidant activity of ebselen and related organoselenium compounds Bioorg. Med. Chem. Lett. 2006, 16, 5334-5338
29. Mugesh, G.; Panda, A.; Singh, H. B.; Punekar, N. S.; Butcher, R. J. Glutathione peroxidase-like antioxidant activity of diaryl diselenides- a mechanistic study J. Am. Chem. Soc. 2001, 123, 839-850
30. Wirth, T. Glutathione peroxidase-like activities of oxygen-containing diselenides Molecules 1998, 3, 164-166
31. Jauslin, M. L.; Wirth, T.; Meier, T.; Schoumacher, F. A cellular model for friedreich ataxia reveals an impaired selenium homeostasis that can be overcome by small-molecule GPx-mimetics Hum. Mol. Genet. 2002, 11, 3055-3063
32. Sun, Y.; Mu, Y.; Ma, S.; Gong, P.; Yan, G.; Liu, J.; Shen, J.; Luo, G. The molecular mechanism of protecting cells against oxidative stress by 2-selenium-bridged β-cyclodextrin with glutathione peroxidase activity Biochim. Biophys. Acta 2005, 1743, 199-204
33. Back, T. G.; Moussa, Z. Remarkable activity of a novel cyclic seleninate ester as a glutathione peroxidase mimetic and its facile in situ generation from allyl-3-hydroxypropyl selenide J. Am. Chem. Soc. 2002, 124, 12104-12105
34. Phadnis, P. P.; Mugesh, G. Internally stabilized selenocysteine derivatives: syntheses, 77Se NMR and biomimetic studies Org. Biomol. Chem. 2005, 3, 2476-2481
35. Zade, S. S.; Singh, H. B.; Butcher, R. J. The isolation and crystal structure of a cyclic selenenate ester derived from bis(2,6-diformyl-4- tert -butylphenyl)diselenide and its glutathione peroxidase-like activity Angew. Chem., Int. Ed. 2004, 43, 4513-4515
36. Andersson, C.-M.; Hallberg, A.; Brattsand, R.; Cotgreave, I. A.; Engman, L.; Persson, J. Glutathione peroxidase-like activity of diaryl tellurides Bioorg. Med. Chem. Lett. 1993, 3, 2553-2558
37. Sarma, B. K.; Manna, D.; Minoura, M.; Mugesh, G. Synthesis, structure, spirocyclization mechanism and glutathione peroxidase-like antioxidant activity of stable spirodiazaselenurane and spirodiazatellurane J. Am. Chem. Soc. 2010, 132, 5364-5374
38. Malmstro, J.; Jonsson, M.; Cotgreave, I. A.; Hammarström, L.; Sjödin, M.; Engman, L. The antioxidant profile of 2,3-dihydrobenzo[b]furan- 5-ol and its 1-thio, 1-seleno, and 1-telluro analogues J. Am. Chem. Soc. 2001, 123, 3434-3440
39. Giles, G. I.; Fry, F. H.; Tasker, K. M.; Holme, A. L.; Peers, C.; Green, K. N.; Klotz, L.-O.; Sies, H.; Jacob, C. Evaluation of sulfur, selenium and tellurium catalysts with antioxidant potential Org. Biomol. Chem. 2003, 1, 4317-4322
40. Nogueira, C. W.; Zeni, G.; Rocha, J. B. T. Organoselenium and Organotellurium Compounds: Toxicology and Pharmacology Chem. Rev. 2004, 104, 6255-6285
41. Braga, A. L.; Alberto, E. E.; Soares, L. C.; Rocha, J. B. T.; Sudati, J. H.; Roos, D. H. Synthesis of telluroamino acid derivatives with remarkable GPx like activity Org. Biomol. Chem. 2009, 7, 43-45
42. Shabaan, S.; Ba, L. A.; Abbas, M.; Burkholz, T.; Denkert, A.; Gohr, A.; Wessjohann, L. A.; Sasse, F.; Weber, W.; Jacob, C. Multicomponent reactions for the synthesis of multifunctional agents with activity against cancer cells Chem. Commun. 2009, 4702-4704
43. Tabuchi, Y.; Sugiyama, N.; Horiuchi, T.; Furusawa, M.; Furuhama, K. Ebselen, a seleno-organic compound, protects against ethanol-induced murine gastric mucosal injury in both in vivo and in vitro systems Eur. J. Pharmacol. 1995, 272, 195-201
44. Pritsos, C. A.; Sokoloff, M.; Gustafson, D. L. PZ-51 (Ebselen) in vivo protection against adriamycin-induced mouse cardiac and hepatic lipid peroxidation and toxicity Biochem. Pharmacol. 1992, 44, 839-841
45. Sies, H. Ebselen, a selenoorganic compound as glutathione peroxidase mimic Free Radical Biol. Med. 1993, 14, 313-323
46. Sarma, B. K.; Mugesh, G. Glutathione peroxidase (GPx)-like antioxidant activity of the organoselenium drug ebselen: unexpected complications with thiol exchange reactions J. Am. Chem. Soc. 2005, 127, 11477-11485
47. Bhabak, K. P.; Mugesh, G. Synthesis, characterization and antioxidant activity of some ebselen analogues Chem.-Eur. J. 2007, 13, 4594-4601
48. Sarma, B. K.; Mugesh, G. Antioxidant activity of the anti-inflammatory compound ebselen: a reversible cyclization pathway via selenenic and seleninic acid intermediates Chem.-Eur. J. 2008, 14, 10603-10614
49. For recent articles about Se···O/N interactions, see
50. Bayse, C. A.; Bakera, R. A.; Ortwinea, K. N. Relative strengths of Se···N, O interactions: implications for glutathione peroxidase activity Inorg. Chim. Acta 2005, 358, 3849-3854
51. Sarma, B. K.; Mugesh, G. Theoretical investigations on the effect of different nitrogen donors on Se···N intramolecular interactions ChemPhysChem 2009, 10, 3013-3020
52. Fischer, H.; Dereu, N. Mechanism of the catalytic reduction of hydroperoxides by ebselen- a 77Se NMR Study Bull. Soc. Chim. Belg. 1987, 96, 757-768
53. Bhabak, K. P.; Mugesh, G. Amide-based glutathione peroxidase mimics: effect of secondary and tertiary amide substituents on antioxidant activity Chem.-Asian J. 2009, 4, 974-983
54. Haenen, G. R. M. M.; Derooij, B. M.; Vermeulen, N. P. E.; Bast, A. Mechanism of the reaction of ebselen with endogenous thiols -dihydrolipoate is a better cofactor than glutathione in the glutathione peroxidase-activity of ebselen Mol. Pharmacol. 1990, 37, 412-422
55. Sarma, B. K.; Mugesh, G. Biomimetic studies on selenoenzymes: modeling the role of proximal histidines in thioredoxin reductases Inorg. Chem. 2006, 45, 5307-5314
56. Mauri, P.; Benazzi, L.; Flohé, L.; Mairorino, M.; Pietta, P. G.; Pilawa, S.; Rovari, A.; Ursini, F. Versatility of selenium catalysis in PHGPx unraveled by LC/ESI-MS/MS Biol. Chem. 2003, 384, 575-588
57. Flohé, L. In Sulfur and selenium catalysis as paradigms for redox regulations, signal transduction by reactive oxygen and nitrogen species: pathways and chemical principles; Forman, H. J.; Fukuto, J.; Torres, M., Eds.; Kluwer Academic Publishers: The Netherlands, 2003.
58. Salmeen, A.; Andersen, J. N.; Myers, M. P.; Meng, T.-C.; Hinks, J. A.; Tonks, N. K.; Barford, D. Redox regulation of protein tyrosine phosphatase 1B involves a sulfenyl-amide intermediate Nature 2003, 423, 769-773
59. van Montfort, R. L. M.; Congreve, M.; Tisi, D.; Carr, R.; Jhoti, H. Oxidation state of the active-site cysteine in protein tyrosine phosphatase 1B Nature 2003, 423, 773-777
60. Sarma, B. K.; Mugesh, G. Redox regulation of protein tyrosine phosphatase 1B (PTP1B): a biomimetic study on the unexpected formation of a sulfenyl amide intermediate J. Am. Chem. Soc. 2007, 129, 8872-8881
61. Sivaramakrishnan, S.; Cummings, A. H.; Gates, K. S. Protection of a single-cysteine redox switch from oxidative destruction: on the functional role of sulfenyl amide formation in the redox-regulated enzyme PTP1B Bioorg. Med. Chem. Lett. 2010, 20, 444-447
62. Mugesh, G.; du Mont, W.-W. Structure-activity correlation between natural glutathione peroxidase(GPx) and mimics: A biomimetic concept for the design and synthesis of more efficient GPx mimics Chem.-Eur. J. 2001, 7, 1365-1370
63. Bhabak, K. P.; Mugesh, G. A synthetic model for the inhibition of glutathione peroxidase by antiarthritic gold compounds Inorg. Chem. 2009, 48, 2449-2455
64. Bhabak, K. P.; Mugesh, G. A simple and efficient strategy to enhance the antioxidant activities of amino-substituted glutathione peroxidase mimics Chem.-Eur. J. 2008, 14, 8640-8651
65. Bhabak, K. P.; Mugesh, G. Synthesis and structure-activity correlation studies of secondary and tertiary amine-based glutathione peroxidase mimics Chem.-Eur. J. 2009, 15, 9846-9854