Biological and Biochemical Aspects of Selenium Compounds

Organoselenium Chemistry: Synthesis and Reactions

Volumn , Issue , 2011, Pages 361-396

  Bhuyan, Bhaskar J ^a   Mugesh, Govindasamy ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Antioxidant activity; Glutathione peroxidase (GPx); Iodothyronine deiodinase (ID); Organoselenium compounds; Reactive oxygen species (ROS); Selenoenzymes; Thioredoxin reductase (TrxR); Thyroid hormones

Indexed keywords

EID: 84878652784     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527641949.ch9     Document Type: Chapter

References (159)

1. Berzelius, J.J. (1818) Afhandl. Fys. Kemi Mineralog., 6, 42.
2. Hutton, J.G. (1931) J. Am. Chem. Soc., 23, 1076.
3. Franke, K.W. (1934) J. Nutr., 8, 597.
4. Franke, K.W. (1934) J. Nutr., 8, 609.
5. Franke, K.W. and Potter, V.R. (1934) J. Nutr., 8, 615.
6. Franke, K.W. (1935) J. Nutr., 10, 223.
7. Franke, K.W. and Painter, E.P. (1935) J. Nutr., 10, 599.
8. Pinsent, J. (1954) Biochem. J., 57, 10.
9. Andreesen, J.R. and Ljungdahl, L. (1973) J. Bacteriol., 116, 867.
10. Turner, D.C. and Stadtman, T.C. (1973) Arch. Biochem. Biophys., 154, 366.
11. Floh é, L., Günzler, E.A., and Schock, H.H. (1973) FEBS Lett., 32, 132.
12. Rotruck, J.T., Pope, A.L., Ganther, H.E., Swason, A.B., and Hoekstra, D.G. (1973) Science, 179, 588.
13. Böck, A. (1994) Selenium proteins containing selenocysteine, in Encyclopedia of Inorganic Chemistry, vol. 8, (ed. R.B. King), John Wiley Ltd, Chichester, UK, p. 370.
14. Floh é, L., Andreesen, J.R., Brigelius-Floh é, R., Maiorino, M., and Ursini, F. (2000) IUBMB Life, 49, 411.
15. Boyington, J.C., Gladyshev, V.N., Khangulov, S.V., Stadtman, T.C., and Sun, P.D. (1997) Science, 275, 1305.
16. Wilting, R., Schorling, S., Persson, B.C., and Böck, A. (1977) J. Mol. Biol., 266, 637.
17. Garcin, E., Vernede, X., Hatchikian, E.C., Volbeda, A., Frey, M., and Fontecilla-Camps, J.C. (1999) Structure, 7, 557.
18. Pfeiffer, M., Bingemann, R., and Klein, A. (1998) Eur. J. Biochem., 256, 447.
19. Wagner, M., Sonntag, D., Grimm, R., Pich, A., Eckerskorn, C., Söhling, B., and Andreesen, J.R. (1999) Eur. J. Biochem., 260, 38.
20. Böck, A., Forchhammer, K., Heider, J., Leinfelder, W., Sawers, G., Veprek, B., and Zinoni, F. (1991) Mol. Microbiol., 5, 515.
21. Stadtman, T.C. (1996) Annu. Rev. Biochem., 65, 83.
22. Dobbek, H., Gremer, L., Meyer, O., and Huber, R. (1999) Proc. Natl. Acad. Sci. U.S.A., 96, 8884.
23. Behne, D., Kyriakopoulos, A., Meinhold, H., and Köhrle, J. (1990) Biochem. Biophys. Res. Commun., 173, 1143.
24. Arthur, J.R., Nicol, F., and Beckett, G.J. (1990) Biochem. J., 272, 537.
25. Davey, J.C., Becker, K.B., Schneider, M.J., Germain, G.L., and Galton, V.A. (1995) J. Biol. Chem., 270, 26786.
26. Croteau, W., Whittemore, S.K., Schneider, M.J., and Germain, D.L. (1995) J. Biol. Chem., 270, 16569.
27. Lescure, A., Gautheret, D., Carbon, P., and Krol, A. (1999) J. Biol. Chem., 274, 38147.
28. Tamura, T., and Stadtman, T.C. (1996) Proc. Natl. Acad. Sci. U.S.A., 93, 1006.
29. Lee, S.R., Kim, J.R., Kwon, K.S., Yoon, H.W., Leveine, R.L., Ginsburg, A., and Rhee, S.G. (1999) J. Biol. Chem., 274, 4722.
30. Watabe, S., Makino, Y., Ogawa, K., Hiroi, T., Yamamoto, Y., and Takahashi, S.Y. (1999) Eur. J. Biochem., 264, 74.
31. Mustacich, D. and Powis, G. (2000) Biochem. J., 346, 1.
32. Mills, G.C. (1957) J. Biol. Chem., 229, 189.
33. Motsenbocker, M.A. and Tappel, A.L. (1984) J. Nutr., 114, 279.
34. Ursini, F., Maiorino, M., Valente, M., Ferri, L., and Gregolin, C. (1982) Biochim. Biophys. Acta, 710, 197.
35. Takahasi, K., Avissar, N., Whittin, J., and Cohen, H. (1987) Arch. Biochem. Biophys., 256, 677.
36. Chu, F.-F., Doroshow, J.H., and Esworthy, R.S. (1993) J. Biol. Chem., 268, 2571.
37. Gromer, S., Eubel, J.K., Lee, B.L., and Jacob, J. (2005) Cell. Mol. Life Sci., 62, 2414.
38. Dietary Supplement Fact Sheet: Selenium. National Institutes of Health; Office of Dietary Supplements, http:// ods.od.nih.gov/factsheets/selenium/ (accessed 5 January 2009).
39. Combs, G.F. (2000) Biofactors, 12, 39.
40. Zimmerman, M.B., and Kohrle, J. (2002) Thyroid, 12, 867.
41. Cahn, R.S., Ingold, C.K., and Prelog, V. (1966) Angew. Chem. Int. Ed., 5, 385.
42. Prelog, V. and Helmchen, G. (1982) Angew. Chem. Int. Ed., 21, 567.
43. Huber, R.E. and Criddle, R.S. (1967) Arch. Biochem. Biophys., 122, 164.
44. Jacob, C., Giles, G.I., Giles, N.M., and Sies, H. (2003) Angew. Chem. Int. Ed., 42, 4742.
45. Walczak, R., Westhof, E., Carbon, P., and Krol, A. (1996) RNA, 2, 367.
46. Sliwkowski, M.X., and Stadtman, T.C. (1985) J. Biol. Chem., 260, 3140.
47. Young, P.A. and Kaiser, I.I. (1975) Arch. Biochem. Biophys., 171, 483.
48. Leinfelder, W., Zehelein, E., Mandrand-Berthelot, M.A., and Böck, A. (1988) Nature, 331, 723.
49. Gladyshev, V.N. and Hatfield, D.L. (1999) J. Biomed. Sci., 6, 151.
50. Kryukov, G.V., Castellano, S., Novoselov, S.V., Lobanov, A.V., Zehtab, O., Guigo, R., and Gladyshev, V.N. (2003) Science, 300, 1439.
51. Sheppard, K., Yuan, J., Hohn, M.J., Jester, B., Devine, K.M., and Söll, D. (2008) Nucleic Acid Res., 36, 1813.
52. Forchhammer, K., Leinfelder, W., Boesmiller, K., Veprek, B., and Böck, A. (1991) J. Biol. Chem., 266, 6318.
53. Yuan, J., Palioura, S., Salazar, J.C., Su, D., O'Donoghue, P., Hohn, M.J., Cardoso, A.M., Whitman, W.B., and Söll, D. (2006) Proc. Natl. Acad. Sci. U.S.A., 103, 18923.
54. Carlson, B.A., Xu, X.M., Kryukov, G.V., Rao, M., Berry, M.J., Gladyshev, V.N., and Hatfield, D.L. (2004) Proc. Natl. Acad. Sci. U.S.A., 101, 12848.
55. Palioura, S., Sherrer, R.L., Steitz, T.A., Söll, D., and Simonovi ć, M. (2009) Science, 325, 321.
56. Fukunaga, R. and Yokoyama, S. (2007) J. Mol. Biol., 370, 128.
57. Fredga, A. (1936) Svensk Kemisk Tidskrift, 48, 160.
58. Chocat, P., Esaki, N., Tanaka, H., and Soda, K. (1985) Anal. Bioanal. Chem., 148, 485.
59. Tanaka, H. and Soda, K. (1987) Meth. Enzymol., 143, 240.
60. Stocking, E.M., Schwarz, J.N., Senn, H., Salzmann, M., and Silks, L.A. (1997) J. Chem. Soc., Perkin Trans. 1, (25) 2443.
61. Siebum, A.H.G., Woo, W.S., Raap, J., and Lugtenburg, J. (2004) Eur. J. Org. Chem., 13, 2905.
62. Theodoropoulos, D., Schwartz, I.L., and Walter, R. (1967) Biochemistry, 6, 3927.
63. Gieselman, M.D., Xie, L., and van Der Donk, W.A. (2001) Org. Lett., 3, 1331.
64. Muttenthaler, M. and Alewood, P.F. (2008) J. Pept. Sci., 14, 1223.
65. Bhuyan, B.J. and Mugesh, G. (2011) Org. Biomol. Chem., 9, 1356.
66. Wieland, T., Bokelmann, E., Bauer, L., Lang, H.U., and Lau, H. (1953) Liebigs Ann. Chem., 583, 129.
67. Dawson, P.E., Muir, T.W., Clark-Lewis, I., and Kent, S.B. (1994) Science, 266, 776.
68. Dawson, P.E. and Kent, S.B. (2000) Annu. Rev. Biochem., 69, 923.
69. Hondal, R.J., Nilsson, B.L., and Raines, R.T. (2001) J. Am. Chem. Soc., 123, 5140.
70. Roelfes, G. and Hilvert, D. (2003) Angew. Chem. Int. Ed., 42, 2275.
71. Roy, G., Sarma, B.K., Phadnis, P.P., and Mugesh, G. (2005) J. Chem. Sci., 117, 287.
72. Quaderer, R., Sewing, A., and Hilvert, D. (2001) Helv. Chim. Acta, 84, 1197.
73. Maiorino, M., Aumann, K.-D., Brigelius-Floh é, R., Doria, R.D., van den Heuvel, L., McCarthy, J., Rovery, A., Ursini, F., and Floh é, L. (1995) Biol. Chem. Hoppe-Seyler, 376, 651.
74. Rocher, C., Lalanne, J.-L., and Chaudiére, J. (1992) Eur. J. Biochem., 205, 955.
75. Maddipati, K.R. and Marnett, L.J. (1987) J. Biol. Chem., 262, 17398.
76. Brigelius-Floh é, R. (1999) Free Radic. Biol. Med., 27, 951.
77. Maiorino, M., Gregolin, C., and Ursini, F. (1990) Meth. Enzymol., 186, 448.
78. Björnstedt, M., Xue, J., Huang, W., Åkesson, B., and Holmgren, A. (1994) J. Biol. Chem., 269, 29382.
79. Maiorino, M., Roveri, A., Coassin, M., and Ursini, F. (1988) Biochem. Pharmacol., 37, 2267.
80. Floh é, L. (1982) Free Radicals in Biology, vol. 5, (ed. W.A. Pryor), Academic Press, New York, p. 223.
81. Epp, O., Ladenstein, R., and Wendel, A. (1983) Eur. J. Biochem., 133, 51-69.
82. Ursini, F., Maiorino, M., Brigelius-Flohé, R., Aumann, K.-D., Roveri, A., Schomburg, D., and Floh é, L. (1995) Meth. Enzymol., 252, 38.
83. Mugesh, G., and Singh, H.B. (2000) Chem. Soc. Rev., 29, 347.
84. Müller, A., Cadenas, E., Graf, P., and Sies, H. (1984) Biochem. Pharmacol., 33, 3235.
85. Wendel, A., Fausel, M., Safayhi, H., Tiegs, G., and Otter, R. (1984) Biochem. Pharmacol., 33, 3241.
86. Sies, H. (1986) Angew. Chem. Int. Ed., 25, 1058.
87. Mugesh, G., du Mont, W.-W., and Sies, H. (2001) Chem. Rev., 101, 2125.
88. Masumoto, H., Kissner, R., Koppenol, W.H., and Sies, H. (1996) FEBS Lett., 398, 179.
89. Noguchi, N., Yoshida, Y., Kaneda, H., Yamamoto, Y., and Niki, E. (1992) Biochem. Pharmacol., 44, 39.
90. Zembowicz, A., Hatchett, R.J., Radziszewski, W., and Gryglewski, R.J. (1993) J. Pharmacol. Exp. Ther., 267, 1112.
91. Hattori, R., Inoue, R., Sase, K., Eizawa, H., Kosuga, K., Aoyama, T., Masayasu, H., Kawai, C., Sasayama, S., and Yui, Y. (1994) Eur. J. Pharmacol., 267, R1.
92. Nikawa, T., Schuch, G., Wagner, G., and Sies, H. (1994) Biochem. Pharmacol., 47, 1007.
93. Lesser, R. and Weiss, R. (1924) Dtsch. Chem. Ges., 57, 1077.
94. Engman, L. and Hallberg, A. (1989) J. Org. Chem., 54, 2964.
95. Zade, S.S., Panda, S., Tripathi, S.K., Singh, H.B., and Wolmershaeuser, G.E. (2004) Eur. J. Org. Chem., 18, 3857.
96. Galet, V., Bernier, J.-L., Hénichart, J.-P., Lesieur, D., Abadie, C., Rochette, L., Lindenbaum, A., Chalas, J., Renaud de la Faverie, J.-F., Pfeiffer, B., and Renard, P. (1994) J. Med. Chem., 37, 2903.
97. Andersson, C.M., Hallberg, A., Brattsand, R., Cotgreave, I.A., Engman, L., and Persson, J. (1993) Bioorg. Med. Chem. Lett., 3, 2553.
98. Wilson, S.R., Zucker, P.A., Huang, R.-R.C., and Spector, A. (1989) J. Am. Chem. Soc., 111, 5936.
99. Iwaoka, M. and Tomoda, S. (1994) J. Am. Chem. Soc., 116, 2557.
100. Jauslin, M.L., Wirth, T., Meier, T., and Schoumacher, F. (2002) Hum. Mol. Genet., 11, 3055.
101. Wirth, T. (1998) Molecules, 3, 164.
102. Sun, Y., Mu, Y., Ma, S., Gong, P., Yan, G., Liu, J., Shen, J., and Luo, G. (2005) Biochim. Biophys. Acta, 1743, 199.
103. Mugesh, G., Panda, A., Singh, H.B., Punekar, N.S., and Butcher, R.J. (2001) J. Am. Chem. Soc., 123, 839.
104. Sarma, B.K., Manna, D., Minoura, M., and Mugesh, G. (2010) J. Am. Chem. Soc., 132, 5364.
105. Wu, Z.-P. and Hilvert, D. (1989) J. Am. Chem. Soc., 111, 4513.
106. Wu, Z.-P. and Hilvert, D. (1990) J. Am. Chem. Soc., 112, 5647.
107. Engman, L., Stern, D., Cotgreave, I.A., and Andersson, C.M. (1992) J. Am. Chem. Soc., 114, 9737.
108. Bell, I.M. and Hilvert, D. (1993) Biochemistry, 32, 13969.
109. Back, T.G. and Dyck, B.P. (2079) J. Am. Chem. Soc., 1997, 119.
110. Fisher, H. and Dereu, N. (1987) Bull. Soc. Chim. Belg., 96, 757.
111. Kice, J.L. and Purkiss, D.W. (1987) J. Org. Chem., 52, 3448.
112. Sarma, B.K. and Mugesh, G. (2005) J. Am. Chem. Soc., 127, 11477.
113. Bhabak, K.P. and Mugesh, G. (2007) Chem. Eur. J., 13, 4594.
114. Sarma, B.K. and Mugesh, G. (2008) Chem. Eur. J., 14, 10603.
115. Bhabak, K.P. and Mugesh, G. (2009) Chem. Asian J., 4, 974.
116. Bhabak, K.P. and Mugesh, G. (2008) Chem. Eur. J., 14, 8640.
117. Bhabak, K.P. and Mugesh, G. (2010) Acc. Chem. Res., 43, 1408.
118. Sarma, B.K. and Mugesh, G. (2008) Org. Biomol. Chem., 6, 965.
119. Back, T.G. and Moussa, Z. (2002) J. Am. Chem. Soc., 124, 12104.
120. Back, T.G. and Moussa, Z. (2003) J. Am. Chem. Soc., 125, 13455.
121. Zade, S.S., Singh, H.B., and Butcher, R.J. (2004) Angew. Chem. Int. Ed., 43, 4513.
122. Werner, S.C. and Ingbar, S. (1991), The Thyroid: A Fundamental and Clinical Text, (eds L.E. Braverman and R.D. Utiger), Lippincott, Philadelphia.
123. Darras, V.M., Hume, R., and Visser, T.J. (1999) Mol. Cell Endocrinol., 151, 37.
124. Carayon, P., and Ruf, J. (1990) Thyroperoxidase and Thyroid Autoimmunity, John Libbey, London.
125. Dunford, H.B. (1999) Heme Peroxidases, John Wiley & Sons, Inc., New York.
126. Visser, T.J., Leonard, J.L., Kaplan, M.M., and Larsen, P.R. (1982) Proc. Natl. Acad. Sci. U.S.A., 79, 5080.
127. Berry, M.J., Banu, L., and Larsen, P.R. (1991) Nature, 349, 438.
128. Köhrle, J. (2005) Thyroid, 15, 841.
129. Camerman, N. and Camerman, A. (1971) Science, 175, 764.
130. Oppenheimer, J.H., Schwartz, H.L., and Surks, M.I. (1972) J. Clin. Invest., 51, 2493.
131. Bianco, A.C., Salvatore, D., Gereben, B., Berry, M.J., and Larsen, P.R. (2002) Endocr. Rev., 23, 38.
132. Köhrle, J. (1999) Mol. Cell. Endocrinol., 151, 103.
133. Bianco, A.C. and Larsen, P.R. (2005) Thyroid, 15, 777.
134. Leonard, J.L., Visser, T.J., and Leonard, D.M. (2001) J. Biol. Chem., 276, 2600.
135. Callebaut, I., Morelli, C.C., Mornon, J.-P., Gereben, B., Buettner, C., Huang, S., Castro, B., Fonseca, T.L., Harney, J.W., Larsen, P.R., and Bianco, A.C. (2003) J. Biol Chem., 278, 36887.
136. Köhrle, J., Jakob, F., Contempr é, B., and Dumont, J.E. (2005) Endocr. Rev., 26, 944.
137. Bianco, A.C. and Kim, B.W. (2006) J. Clin. Invet., 116, 2571.
138. Dentice, M., Bandyopadhyay, A., Gereben, B., Callebaut, I., Christoffolete, M.A., Kim, B.W., Nissim, S., Mornon, J.-P., Zavacki1, A.M., Zeöld, A., Capelo, L.P., Morelli, C.C., Ribeiro, R., Harney, J.W., Tabin, C.J., and Bianco, A.C. (2005) Nat. Cell Biol., 7, 698.
139. Roy, G., Nethaji, M., and Mugesh, G. (2004) J Am. Chem. Soc., 126, 2712.
140. Roy, G. and Mugesh, G. (2005) J Am. Chem. Soc., 127, 15207.
141. Berry, M.J., Kieffer, J.D., Harney, J.W., and Larsen, P.R. (1991) J. Biol. Chem., 266, 14155.
142. Köhrle, J. (2002) Meth. Enzymol., 347, 125.
143. Beck, C., Jensen, S.B., and Reglinski, J. (1994) Bioorg. Med. Chem. Lett., 4, 1353.
144. Vasil'ev, A.A. and Engman, L. (1998) J. Org. Chem., 63, 3911.
145. Goto, K., Sonoda, D., Shimada, K., Sase, S., and Kawashima, T. (2010) Angew. Chem. Int. Ed., 49, 545-547.
146. Manna, D. and Mugesh, G. (2010) Angew. Chem. Int. Ed., 49, 9246.
147. Sun, B.C., Harney, J.W., Berry, M.J., and Larsen, P.R. (1997) Endocrinology, 138, 5452.
148. Andersen, J.F., Sanders, D.A.R., Gasdaska, J.R., Weichsel, A., Powis, G., and Montfort, W.R. (1997) Biochemistry, 36, 13979.
149. Freemerman, A.J., Gallegos, A., and Powis, G. (1999) Cancer Res., 59, 4090.
150. Oblong, J.E., Berggren, M., Gasdaska, P.Y., and Powis, G. (1994) J. Biol. Chem., 269, 11714.
151. Sarma, B.K. and Mugesh, G. (2006) Inorg. Chem., 45, 5307.
152. Sandalova, T., Zhong, L., Lindqvist, Y., Holmgren, A., and Schneider, G. (2001) Proc. Natl. Acad. Sci. U.S.A., 98, 9533.
153. Cheng, Q., Sandalova, T., Lindqvist, Y., and Arnér, E.S.J. (2009) J. Biol. Chem., 284, 3998.
154. Deponte, M., Urig, S., Arscott, L.D., Fritz-Wolf, K.R.R., Herold-Mende, C., Koncarevic, S., Meyer, M., Davioud-Charvet, E., Ballou, D.P., Williams, C.H., Jr., and Becker, K. (2005) J. Biol. Chem., 280, 20628.
155. Schröder, D., Schwarz, H., Hrušák, J., and Pyykk ö, P. (1998) Inorg. Chem., 37, 624.
156. Filipovska, A., Kelso, G.F., Brown, S.E., Beer, S.M., Smith, R.A., and Murphy, M.P. (2005) J. Biol. Chem., 280, 24113.
157. Isab, A.A., Hormann, A.L., Coffer, M.T., and Shaw, C.F. (1988) J. Am. Chem. Soc., 110, 3278.
158. Coffer, M.T., Shaw, C.F., Hormann, A.L., Mirabelli, C.K., and Crooke, S.T. (1987) J. Inorg. Biochem., 30, 177.
159. Brandt, W. and Wessjohann, L.A. (2005) ChemBioChem, 6, 386.