Effects of methoxy substituents on the glutathione peroxidase-like activity of cyclic seleninate esters

Journal of Organic Chemistry

Volumn 79, Issue 19, 2014, Pages 9394-9401

  Press, David J ^a   McNeil, Nicole M R ^a   Hambrook, Miranda ^a   Back, Thomas G ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERIFICATION; ESTERS; PEPTIDES;

ANTIOXIDANT ENZYME; GLUTATHIONE PEROXIDASE; MESOMERIC; METHOXY GROUP; O-METHOXY; SELENINATE ESTERS; SINGLE ELECTRON; STERIC EFFECT;

CATALYST ACTIVITY;

ALUMINUM LITHIUM HYDRIDE; CARBONYL DERIVATIVE; CYCLIC SELENINATE ESTER; DISULFIDE; ESTER; GLUTATHIONE PEROXIDASE; SELENIUM DERIVATIVE; THIOL; UNCLASSIFIED DRUG; ANTIOXIDANT; HYDROGEN PEROXIDE; ORGANOSELENIUM DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHROMATOGRAPHY; COMPARATIVE STUDY; CYCLIZATION; ELECTROSPRAY; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; IN VITRO STUDY; METHANOLYSIS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; SYNTHESIS; CATALYSIS; CHEMISTRY; METABOLISM; MOLECULAR MIMICRY;

ANTIOXIDANTS; CATALYSIS; ESTERS; GLUTATHIONE PEROXIDASE; HYDROGEN PEROXIDE; MOLECULAR MIMICRY; ORGANOSELENIUM COMPOUNDS; SULFHYDRYL COMPOUNDS;

EID: 84907790134     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo501689h     Document Type: Article

References (81)

1. Rotruck, J. T.; Pope, A. L.; Ganther, H. E.; Swanson, A. B.; Hafeman, D. G.; Hoekstra, W. G. Science 1973, 179, 588-590
2. Flohé, L.; Günzler, W. A.; Schock, H. H. FEBS Lett. 1973, 32, 132-134
3. Arthur, J. R. Cell. Mol. Life Sci. 2000, 57, 1825-1835
4. Brigelius-Flohé, R.; Maiorino, M. Biochim. Biophys. Acta 2013, 1830, 3289-3303
5. Brigelius-Flohé, R.; Kipp, A. P. Ann. N. Y. Acad. Sci. 2012, 1259, 19-25
6. Stadtman, T. C. J. Biol. Chem. 1991, 266, 16257-16260
7. Tappel, A. L. Curr. Top. Cell Regul. 1984, 24, 87-97
8. Flohé, L. Curr. Top. Cell Regul. 1985, 27, 473-478
9. Ganther, H. E. Chem. Scr. 1975, 8a, 79-84
10. Epp, O.; Ladenstein, R.; Wendel, A. Eur. J. Biochem. 1983, 133, 51-69
11. Nogueira, C. W.; Rocha, J. B. T. In Organic Selenium and Tellurium Compounds; Rappoport, Z., Ed.; Wiley: Chichester, U.K., 2012; Vol. 3, Part II, Chapter 21.
12. Masukawa, T. In The Chemistry of Organoselenium and Tellurium Compounds; Patai, S., Ed.; Wiley: Chichester, U.K., 1987; Vol. 2, Chapter 9.
13. Brenneisen, P.; Steinbrenner, H.; Sies, H. Mol. Aspects Med. 2005, 26, 256-267
14. Sies, H., Ed. Oxidative Stress; Academic Press: London, 1985.
15. Rice-Evans, C.; Halliwell, B.; Lunt, G. G., Eds. Free Radicals and Oxidative Stress: Environment, Drugs and Food Additives; Portland Press: London, 1995.
16. Paoletti, R.; Samuelsson, B.; Catapano, A. L.; Poli, A.; Rinetti, M., Eds. Oxidative Processes and Antioxidants; Raven Press: New York, 1994.
17. Burk, R. F., Ed. Selenium in Biology and Human Health; Springer-Verlag: New York, 1994.
18. Crack, P. J.; Taylor, J. M.; de Haan, J. B.; Kola, I.; Hertzog, P.; Iannello, R. C. J. Cereb. Blood Flow Metab. 2003, 23, 19-22
19. Wong, C. H. Y.; Bozinovski, S.; Hertzog, P. J.; Hickey, M. J.; Crack, P. J. J. Neurochem. 2008, 107, 241-252
20. Dhalla, N. S.; Elmoselhi, A. B.; Hata, T.; Makino, N. Cardiovasc. Res. 2000, 47, 446-456
21. Lim, C. C.; Bryan, N. S.; Jain, M.; Garcia-Saura, M. F.; Fernandez, B. O.; Sawyer, D. B.; Handy, D. E.; Loscalzo, J.; Feelisch, M.; Liao, R. Am. J. Physiol. Heart Circ. Physiol. 2009, 297, H2144-H2153
22. Maulik, N.; Yoshida, T.; Das, D. K. Mol. Cell. Biochem. 1999, 196, 13-21
23. Mužáková, V.; Kandár, R.; Vojtíšek, P.; Skalický, J.; Vaňková, R.; Čegan, A.; Červinková, Z. Physiol. Res. 2001, 50, 389-396
24. Moutet, M.; D'Alessio, P.; Malette, P.; Devaux, V.; Chaudière, J. Free Radical Biol. Med. 1998, 25, 270-281
25. Ganther, H. E.; Kraus, R. J. In Methods in Enzymology; Colowick, S. P.; Kaplan, N. O., Eds.; Academic Press: Orlando, FL, 1984; Vol. 107, pp 593-602.
26. Day, B. J. Biochem. Pharmacol. 2009, 77, 285-296
27. Bhabak, K. P.; Mugesh, G. Acc. Chem. Res. 2010, 43, 1408-1419
28. Mugesh, G.; Singh, H. B. Chem. Soc. Rev. 2000, 29, 347-357
29. Mugesh, G.; du Mont, W.-W.; Sies, H. Chem. Rev. 2001, 101, 2125-2179
30. Müller, A.; Cadenas, E.; Graf, P.; Sies, H. Biochem. Pharmacol. 1984, 33, 3235-3239
31. Wendel, A.; Fausel, M.; Safayhi, H.; Tiegs, G.; Otter, R. Biochem. Pharmacol. 1984, 33, 3241-3245
32. Parnham, M. J.; Kindt, S. Biochem. Pharmacol. 1984, 33, 3247-3250
33. Müller, A.; Gabriel, H.; Sies, H. Biochem. Pharmacol. 1985, 34, 1185-1189
34. Safayhi, H.; Tiegs, G.; Wendel, A. Biochem. Pharmacol. 1985, 34, 2691-2694
35. Wendel, A.; Tiegs, G. Biochem. Pharmacol. 1986, 35, 2115-2118
36. Fischer, H.; Dereu, N. Bull. Soc. Chim. Belg. 1987, 96, 757-768
37. Haenen, G. R. M. M.; De Rooij, B. M.; Vermeulen, N. P. E.; Bast, A. Mol. Pharmacol. 1990, 37, 412-422
38. Glass, R. S.; Farooqui, F.; Sabahi, M.; Ehler, K. W. J. Org. Chem. 1989, 54, 1092-1097
39. Bhabak, K. P.; Mugesh, G. Chem.-Eur. J. 2007, 13, 4594-4601
40. Sarma, B. K.; Mugesh, G. Chem.-Eur. J. 2008, 14, 10603-10614
41. Bhabak, K. P.; Vernekar, A. A.; Jakka, S. R.; Roy, G.; Mugesh, G. Org. Biomol. Chem. 2011, 9, 5193-5200
42. Selvakumar, K.; Shah, P.; Singh, H. B.; Butcher, R. J. Chem.-Eur. J. 2011, 17, 12741-12755
43. Sarma, B. K.; Mugesh, G. J. Am. Chem. Soc. 2005, 127, 11477-11485
44. Jacquemin, P. V.; Christiaens, L. E.; Renson, M.; Evers, M. J.; Dereu, N. Tetrahedron Lett. 1992, 33, 3863-3866
45. Asaf, R.; Blum, S.; Miller-Lotan, R.; Levy, A. P. Lett. Drug Des. Discovery 2007, 4, 160-162
46. Castagné, V.; Clarke, P. G. H. J. Neurosci. Res. 2000, 59, 497-503
47. Back, T. G.; Moussa, Z. J. Am. Chem. Soc. 2002, 124, 12104-12105
48. Back, T. G.; Moussa, Z. J. Am. Chem. Soc. 2003, 125, 13455-13460
49. Back, T. G.; Kuzma, D.; Parvez, M. J. Org. Chem. 2005, 70, 9230-9236
50. Press, D. J.; Mercier, E. A.; Kuzma, D.; Back, T. G. J. Org. Chem. 2008, 73, 4252-4255
51. McNeil, N. M. R.; Matz, M. C.; Back, T. G. J. Org. Chem. 2013, 78, 10369-10382
52. Tripathi, S. K.; Patel, U.; Roy, D.; Sunoj, R. B.; Singh, H. B.; Wolmershäuser, G.; Butcher, R. J. J. Org. Chem. 2005, 70, 9237-9247
53. Tripathi, S. K.; Sharma, S.; Singh, H. B.; Butcher, R. J. Org. Biomol. Chem. 2011, 9, 581-587
54. Singh, V. P.; Singh, H. B.; Butcher, R. J. Chem.-Asian J. 2011, 6, 1431-1442
55. Bayse, C. A.; Ortwine, K. N. Eur. J. Inorg. Chem. 2013, 3680-3688
56. For a discussion of these effects, see: Sykes, P. A Guidebook to Mechanism in Organic Chemistry, 6th ed.; Pearson Prentice-Hall: Harlow, U.K., 1986; Chapter 13.
57. Bhabak, K. P.; Mugesh, G. Chem.-Eur. J. 2008, 14, 8640-8651
58. Bhowmick, D.; Mugesh, G. Tetrahedron 2012, 68, 10550-10560
59. Wirth, T. Molecules 1998, 3, 164-166
60. Mukherjee, A. J.; Zade, S. S.; Singh, H. B.; Sunoj, R. B. Chem. Rev. 2010, 110, 4357-4416
61. Mugesh, G.; Panda, A.; Singh, H. B.; Punekar, N. S.; Butcher, R. J. J. Am. Chem. Soc. 2001, 123, 839-850
62. Iwaoka, M.; Komatsu, H.; Katsuda, T.; Tomoda, S. J. Am. Chem. Soc. 2004, 126, 5309-5317
63. Iwaoka, M.; Tomoda, S. J. Am. Chem. Soc. 1994, 116, 2557-2561
64. Comins, D. L.; Brown, J. D. J. Org. Chem. 1984, 49, 1078-1083
65. Back, T. G.; Moussa, Z.; Parvez, M. Angew. Chem., Int. Ed. 2004, 43, 1268-1270
66. Press, D. J.; McNeil, N. M. R.; Rauk, A.; Back, T. G. J. Org. Chem. 2012, 77, 9268-9276
67. Back, T. G.; Dyck, B. P. J. Am. Chem. Soc. 1997, 119, 2079-2083
68. Mercier, E. A.; Smith, C. D.; Parvez, M.; Back, T. G. J. Org. Chem. 2012, 77, 3508-3517
69. Freeman, F.; Angeletakis, C. N. J. Am. Chem. Soc. 1983, 105, 4039-4049
70. For a review of sulfines, see: Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1982, 101, 1-27
71. Strating, J.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1967, 86, 641-650
72. Snyder, J. P. J. Am. Chem. Soc. 1974, 96, 5005-5007
73. Hydrogen peroxide was titrated by the procedure described in: Jeffery, G. H.; Bassett, J.; Mendham, J.; Denney, R. C., Eds. Vogel's Textbook of Quantitative Chemical Analysis, 5th ed.; Wiley: New York, 1989; pp 372-373.
74. Lynett, P. T.; Butts, K.; Vaidya, V.; Garrett, G. E.; Pratt, D. A. Org. Biomol. Chem. 2011, 9, 3320-3330
75. Freeman, F.; Angeletakis, C. N.; Maricich, T. J. Org. Magn. Reson. 1981, 17, 53-58
76. Stensaas, K. L.; Brownell, A. S.; Ahuja, S.; Harriss, J. K.; Herman, S. R. J. Sulfur Chem. 2008, 29, 433-443
77. Bretschneider, H.; Klotzer, W. Monatsh. Chem. 1950, 81, 589-597
78. Hayashi, S.; Furukawa, M.; Yamamoto, J.; Hamamura, K. Chem. Pharm. Bull. 1967, 15, 1310-1314
79. Bravo, A.; Dordi, B.; Fontana, F.; Minisci, F. J. Org. Chem. 2001, 66, 3232-3234
80. Brownbridge, P.; Jowett, I. C. Synthesis 1988, 252-254
81. Duddeck, H. Prog. Nucl. Magn. Reson. Spectrosc. 1995, 27, 1-323