Amide-based glutathione peroxidase mimics: Effect of secondary and amide substituents on antioxidant activity

Chemistry - An Asian Journal

Volumn 4, Issue 6, 2009, Pages 974-983

  Bhabak, Krishna P ^a   Mugesh, Govindasamy ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Antioxidants; Catalysis; Redox chemistry; Selenium; Thiol exchange

Indexed keywords

AMIDE MOIETIES; ANTIOXIDANT ACTIVITIES; ANTIOXIDANTS; CATALYTIC ACTIVITY; CATALYTIC CYCLES; CO-SUBSTRATE; DISELENIDES; DISPROPORTIONATION; EFFECT OF SUBSTITUTION; GLUTATHIONE PEROXIDASE; NH GROUPS; NONBONDED INTERACTION; REDOX CHEMISTRY; SELENINIC ACIDS; TERTIARY AMIDES; THIOL EXCHANGE; THIOL EXCHANGE REACTIONS;

CATALYSIS; SELENIUM; SELENIUM COMPOUNDS; SUBSTRATES; SULFUR COMPOUNDS;

AMIDES;

AMIDE; ANTIOXIDANT; CARBOXYLIC ACID; GLUTATHIONE PEROXIDASE; HYDROGEN PEROXIDE; ORGANOSELENIUM DERIVATIVE; SELENINIC ACID;

ARTICLE; BIOMIMETICS; CATALYSIS; CHEMISTRY; KINETICS; METABOLISM;

AMIDES; ANTIOXIDANTS; BIOMIMETICS; CARBOXYLIC ACIDS; CATALYSIS; GLUTATHIONE PEROXIDASE; HYDROGEN PEROXIDE; KINETICS; ORGANOSELENIUM COMPOUNDS;

EID: 67650666166     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200800483     Document Type: Article

References (62)

1. L. Flohe, E. A. Günzler, H. H. Schock, FEBS Lett. 1973, 32, 132-134;
2. J. T. Rotruck, A. L. Pope, H. E. Ganther, A. B. Swanson, D. G. Hafeman, W. G. Hoekstra, Science 1973, 179, 588-590;
3. O. Epp, R. Ladenstein, A. Wendel, Eur. J. Biochem. 1983, 133, 51-69;
4. Selenium in Biology and Human Health (Ed.: R. F. Burk), Springer, NewYork, 1994;
5. G. Mugesh, W. W. du Mont, Chem. Eur. J. 2001, 7, 1365-1370;
6. C. Jacob, G. I. Giles, N. M. Giles, H. Sies, Angew. Chem. 2003, 115, 4890-4907; Angew. Chem. Int. Ed. 2003, 42, 4742-4758;
7. G. Roy, B. K. Sarma, P. P. Phadnis, G. Mugesh, J. Chem. Sci. 2005, 117, 28-303
8. H. Sies, Oxidative Stress: Introductory Remarks, in Oxidative Stress (Ed.: H. Sies), Academic Press, London, 1985, pp. 1-8;
9. H. Sies, Angew. Chem. 1986, 98, 1061-1075; Angew. Chem. Int. Ed. Engl. 1986, 25, 1058-1071.
10. A. Müller, E. Cadenas, P. Graf, H. Sies, Biochem. Pharmacol. 1984, 33, 3235-3240;
11. A. Wendel, M. Fausel, H. Safayhi, G. Tiegs, R. Otter, Biochem. Pharmacol. 1984, 33, 3241-3246;
12. G. Mugesh, H. B. Singh, Chem. Soc. Rev. 2000, 29, 347-357;
13. G. Mugesh, W. W. du Mont, H. Sies, Chem. Rev. 2001, 101, 2125-2179.
14. P. V. Jacquemin, L. E. Christiaens, M. J. Renson, M. J. Evers, N. Dereu, Tetrahedron Lett. 1992, 33, 3863-3866;
15. T. G. Back, B. P. Dyck, J. Am. Chem. Soc. 1997, 119, 2079-2083
16. H. J. Reich, C. P. Jasperse, J. Am. Chem. Soc. 1987, 109, 5549-5551;
17. L. Engman, A. Hallberg, J. Org. Chem. 1989, 54, 2964-2966;
18. M. Iwaoka, S. Tomoda, J. Am. Chem. Soc. 1994, 116, 2557-2561;
19. T. Wirth, Molecules 1998, 3, 164-166;
20. G. Mugesh, A. Panda, H. B. Singh, N. S. Punekar, R. J. Butcher, J. Am. Chem. Soc. 2001, 123, 839-850;
21. M. L. Jauslin, T. Wirth, T. Meier, F. Schoumacher, Hum. Mol. Genet. 2002, 11, 3055-3063;
22. Y. Sun, Y. Mu, S. Ma, P. Gong, G. Yan, J. Liu, J. Shen, G. Luo, Biochim. Biophys. Acta Mol. Cell Res. 2005, 1743, 199-204;
23. K. P. Bhabak, G. Mugesh, Chem. Eur. J. 2008, 14, 8640-8651.
24. T. G. Back, Z. Moussa, J. Am. Chem. Soc. 2002, 124, 12104-12105;
25. T. G. Back, Z. Moussa, J. Am. Chem. Soc. 2003, 125, 13455-13460.
26. B. Ren, W. Huang, B. Åkesson, R. Ladenstein, J. Mol. Biol. 1997, 268, 869-885.
27. S. Benkova, J. Kóň a, G. Gann, W. M. F. Fabian, Int. J. Quantum Chem. 2002, 90, 555-565;
28. S. M. Bachrach, D. W. Demoin, M. Luk, J. V., Jr. Miller, J. Phys. Chem. A 2004, 108, 4040-4046;
29. C. A. Bayse, J. Phys. Chem. A 2007, 111, 9070-9075.
30. M. Iwaoka, S. Tomoda, J. Am. Chem. Soc. 1996, 118, 8077-8084;
31. W. Nakanishi S. Hayashi, S. Toyota, Chem. Commun. 1996, 371-372;
32. T. Wirth, G. Fragale, M. Spichty, J. Am. Chem. Soc. 1998, 120, 3376-3381;
33. W. Nakanishi, S. Hayashi, A. Sakaue, G. Ono, Y. Kawada, J. Am. Chem. Soc. 1998, 120, 3635-3640;
34. H. Komatsu, M. Iwaoka, S. Tomoda, Chem. Commun. 1999, 205-206;
35. M. Spichty, G. Fragale, T. Wirth, J. Am. Chem. Soc. 2000, 122, 10914-10916;
36. M. Iwaoka, H. Komatsu, T. Katsuda, S. Tomoda, J. Am. Chem. Soc. 2002, 124, 1902-1909;
37. M. Iwaoka, H. Komatsu, T. Katsuda, S. Tomoda, J. Am. Chem. Soc. 2004, 126, 5309-5317
38. M. Iwaoka, T. Katsuda, H. Komatsu, S. Tomoda, J. Org. Chem. 2005, 70, 321-327;
39. C. A. Bayse, R. A. Baker, K. N. Ortwine, Inorg. Chim. Acta 2005, 358, 3849-3854.
40. B. K. Sarma, G. Mugesh, J. Am. Chem. Soc. 2005, 127, 11477-11485;
41. K. P. Bhabak, G. Mugesh, Chem. Eur. J. 2007, 13, 4594-4601;
42. B. K. Sarma, G. Mugesh, Org. Biomol. Chem. 2008, 6, 965-974;
43. B. K. Sarma, G. Mugesh, Chem. Eur. J. 2008, 14, 10603-10614.
44. 2. In this particular example, the structure of selenonic acid was unambiguously confirmed by single crystal Xray diffraction studies.
45. C. Little, R. Olinescu, K. G. Reid, P. J. O'Brien, J. Biol. Chem. 1970, 245, 3632-3636;
46. L. Flohé, I. Brand, Biochim. Biophys. Acta Enzymol 1969, 191, 529-541;
47. F. M. Maiorino, R. Brigelius-Flohé, K. D. Aumann, A. Roveri, D. Schomburg, L. Flohé, Methods Enzymol. 1995, 252, 38- 48.
48. H. Fischer, N. Dereu, P. Kuhl, E. Graf, A. Wendel, Ger. Offen. 1986, 23 pp. CODEN: GWXXBX DE 3513071A1 19861023 CAN 106:32613 AN 1987:32613.
49. M. Osajda, K. Kloc, J. Mlochowski, E. Piasecki, K. Rybka, Pol. J. Chem. 2001, 75, 823-830.
50. A. Welter, H. Fischer, L. Christiaens, A. Wendel, E. Etschenberg, Ger. Offen. 1986, 26 pp. CODEN: GWXXBX DE 3513070A1 19861030 CAN 106:84181 AN 1987:84181;
51. M. Piatek, B. Oleksyn, J. Sliwinski, Acta Crystallogr. Sect. C, Cryst. Str. Commun. 1995, C51, 298-301.
52. Gaussian 98, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Al-. Keith, M. A. Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. J. Replogle, A. J. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
53. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789;
54. A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
55. A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899-926;
56. E. D. Glendening, J. E. Reed, J. E. Carpenter, F. Weinhold, Natural Bond Orbital (NBO) Version 3.1.
57. J. B. Foresman, T. A. Keith, K. B. Wiberg, J. Snoonian, M. J. Frisch, J. Phys. Chem. 1996, 100, 16098-16104.
58. SMART, Version 5.05, Bruker AXS, Madison, WI, 1998
59. A. Altomare, G. Cascarano, C. Giacovazzo, A. Gualardi, J. Appl. Crystallogr. J. Appl. Cryst. 1993, 26, 343-350.
60. G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473;
61. G. M. Sheldrick, SHELX-97, Program for the Refinement of Crystal Structures, University of Gçttingen, Gçttingen, Germany, 1997.
62. CCDC 714684 (17) CCDC 616458 (20), CCDC 713847 (48), CCDC 713848 (52) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre at www.ccdc.cam.ac.uk/data-request/cif.