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Chemical Compound Review

SeMet     (2S)-2-amino-4-methylselanyl- butanoic acid

Synonyms: Megavite RX, PubChem13834, CHEMBL113178, AG-D-90808, CHEBI:30021, ...
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Disease relevance of Selenomethionine


High impact information on Selenomethionine


Chemical compound and disease context of Selenomethionine


Biological context of Selenomethionine


Anatomical context of Selenomethionine

  • GPx, like selenomethionine, protected against protein 3-nitrotyrosine formation in human fibroblast lysates, shown in Western blots [19].
  • Glial cells contained seven 75Se(2+)-labeled proteins ranging in size from 12 to 62 kDa, none of which corresponded to the type II substrate binding subunit. these data show that, unlike the type I enzyme, the type II enzyme does not contain a selenocysteine or selenomethionine, further emphasizing the differences between these two isozymes [20].
  • Accessible tissues such as red blood cells were highly labeled (20-25%) in the subjects receiving selenomethionine [21].
  • Upon incubation of J-774 A.1 macrophages with selenomethionine (10 ng/ml) for 1 week, cellular GSH content and GPx activity were increased by about twofold compared to control cells, and this effect was associated with a 30% reduction in cell-mediated oxidation of LDL [22].
  • Infants fed human milk from women receiving 0 or 200 micrograms supplemental selenium as selenomethionine or selenium-enriched yeast had plasma selenium that paralleled changes in their selenium intake [23].

Associations of Selenomethionine with other chemical compounds


Gene context of Selenomethionine

  • The crystal structure of Rv1347c was determined by multiwavelength anomalous diffraction phasing from selenomethionine-substituted protein and refined at 2.2 angstrom resolution (r = 0.227, R(free) = 0.257) [28].
  • On the basis of RT-PCR analysis, SM and p-XSC increased p53 gene expression by 2-fold in AR cells but not in AI cells and only SM enhanced epidermal growth factor receptor in AR cells [29].
  • Selenomethionine induces sustained ERK phosphorylation leading to cell-cycle arrest in human colon cancer cells [30].
  • Both p-XSC and p-XMS reduced cell number and total protein concentration compared to control-treated AR and AI cells, while SM and MSC exhibited no effect on growth of AR and AI cells [29].
  • The technique of multiple-wavelength anomalous dispersion (MAD) with the selenomethionine form of IL-1 alpha was utilized in combination with a single mercury derivative to provide the starting phases [31].

Analytical, diagnostic and therapeutic context of Selenomethionine


  1. Effects of dietary selenium supplementation on DNA damage and apoptosis in canine prostate. Waters, D.J., Shen, S., Cooley, D.M., Bostwick, D.G., Qian, J., Combs, G.F., Glickman, L.T., Oteham, C., Schlittler, D., Morris, J.S. J. Natl. Cancer Inst. (2003) [Pubmed]
  2. Screening for pancreatic disease: A comparison of grey-scale ultrasonography and isotope scanning. Berger, L.A., Rhodes, J.M., Agnew, J.E., Horrocks, R.A., Chudleigh, P.M., Elias, E., Summerfield, J.A. Lancet (1979) [Pubmed]
  3. Randomized, placebo-controlled, esophageal squamous cell cancer chemoprevention trial of selenomethionine and celecoxib. Limburg, P.J., Wei, W., Ahnen, D.J., Qiao, Y., Hawk, E.T., Wang, G., Giffen, C.A., Wang, G., Roth, M.J., Lu, N., Korn, E.L., Ma, Y., Caldwell, K.L., Dong, Z., Taylor, P.R., Dawsey, S.M. Gastroenterology (2005) [Pubmed]
  4. Selenomethionyl proteins produced for analysis by multiwavelength anomalous diffraction (MAD): a vehicle for direct determination of three-dimensional structure. Hendrickson, W.A., Horton, J.R., LeMaster, D.M. EMBO J. (1990) [Pubmed]
  5. Differential effect of dietary methionine on the biopotency of selenomethionine and selenite in cancer chemoprevention. Ip, C. J. Natl. Cancer Inst. (1988) [Pubmed]
  6. Vitamin E succinate inhibits the function of androgen receptor and the expression of prostate-specific antigen in prostate cancer cells. Zhang, Y., Ni, J., Messing, E.M., Chang, E., Yang, C.R., Yeh, S. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  7. Selenomethionine regulation of p53 by a ref1-dependent redox mechanism. Seo, Y.R., Kelley, M.R., Smith, M.L. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  8. Adaptive responses and apoptosis in endothelial cells exposed to carbon monoxide. Thom, S.R., Fisher, D., Xu, Y.A., Notarfrancesco, K., Ischiropoulos, H. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  9. A selenomethionine-containing azurin from an auxotroph of Pseudomonas aeruginosa. Frank, P., Licht, A., Tullius, T.D., Hodgson, K.O., Pecht, I. J. Biol. Chem. (1985) [Pubmed]
  10. The crystal structure of E.coli 1-deoxy-D-xylulose-5-phosphate reductoisomerase in a ternary complex with the antimalarial compound fosmidomycin and NADPH reveals a tight-binding closed enzyme conformation. Mac Sweeney, A., Lange, R., Fernandes, R.P., Schulz, H., Dale, G.E., Douangamath, A., Proteau, P.J., Oefner, C. J. Mol. Biol. (2005) [Pubmed]
  11. Crystal structure of NADP(H)-dependent 1,5-anhydro-D-fructose reductase from Sinorhizobium morelense at 2.2 A resolution: construction of a NADH-accepting mutant and its application in rare sugar synthesis. Dambe, T.R., Kühn, A.M., Brossette, T., Giffhorn, F., Scheidig, A.J. Biochemistry (2006) [Pubmed]
  12. X-ray crystal structures of HMG-CoA synthase from Enterococcus faecalis and a complex with its second substrate/inhibitor acetoacetyl-CoA. Steussy, C.N., Vartia, A.A., Burgner, J.W., Sutherlin, A., Rodwell, V.W., Stauffacher, C.V. Biochemistry (2005) [Pubmed]
  13. The high-resolution structure of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase reveals a twist in the plane of bound phosphoenolpyruvate. Shumilin, I.A., Bauerle, R., Kretsinger, R.H. Biochemistry (2003) [Pubmed]
  14. Methionine analogs and cell division regulation in the yeast Saccharomyces cerevisiae. Singer, R.A., Johnston, G.C., Bedard, D. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  15. Methioninase cancer gene therapy with selenomethionine as suicide prodrug substrate. Miki, K., Xu, M., Gupta, A., Ba, Y., Tan, Y., Al-Refaie, W., Bouvet, M., Makuuchi, M., Moossa, A.R., Hoffman, R.M. Cancer Res. (2001) [Pubmed]
  16. Selenomethionine induction of DNA repair response in human fibroblasts. Seo, Y.R., Sweeney, C., Smith, M.L. Oncogene (2002) [Pubmed]
  17. A phase I and pharmacokinetic study of fixed-dose selenomethionine and irinotecan in solid tumors. Fakih, M.G., Pendyala, L., Smith, P.F., Creaven, P.J., Reid, M.E., Badmaev, V., Azrak, R.G., Prey, J.D., Lawrence, D., Rustum, Y.M. Clin. Cancer Res. (2006) [Pubmed]
  18. An essential role of s-adenosyl-L-methionine:L-methionine s-methyltransferase in selenium volatilization by plants. Methylation of selenomethionine to selenium-methyl-L-selenium- methionine, the precursor of volatile selenium. Tagmount, A., Berken, A., Terry, N. Plant Physiol. (2002) [Pubmed]
  19. Glutathione peroxidase protects against peroxynitrite-mediated oxidations. A new function for selenoproteins as peroxynitrite reductase. Sies, H., Sharov, V.S., Klotz, L.O., Briviba, K. J. Biol. Chem. (1997) [Pubmed]
  20. Evidence that type II 5'-deiodinase is not a selenoprotein. Safran, M., Farwell, A.P., Leonard, J.L. J. Biol. Chem. (1991) [Pubmed]
  21. Selenium utilization in humans--a long-term, self-labeling experiment with stable isotopes. Veillon, C., Patterson, K.Y., Button, L.N., Sytkowski, A.J. Am. J. Clin. Nutr. (1990) [Pubmed]
  22. Macrophage glutathione content and glutathione peroxidase activity are inversely related to cell-mediated oxidation of LDL: in vitro and in vivo studies. Rosenblat, M., Aviram, M. Free Radic. Biol. Med. (1998) [Pubmed]
  23. Selenium status of infants is influenced by supplementation of formula or maternal diets. McGuire, M.K., Burgert, S.L., Milner, J.A., Glass, L., Kummer, R., Deering, R., Boucek, R., Picciano, M.F. Am. J. Clin. Nutr. (1993) [Pubmed]
  24. Effect of an inorganic and organic form of dietary selenium on the promotional stage of mammary carcinogenesis in the rat. Thompson, H.J., Meeker, L.D., Kokoska, S. Cancer Res. (1984) [Pubmed]
  25. Gene expression differences in normal esophageal mucosa associated with regression and progression of mild and moderate squamous dysplasia in a high-risk Chinese population. Joshi, N., Johnson, L.L., Wei, W.Q., Abnet, C.C., Dong, Z.W., Taylor, P.R., Limburg, P.J., Dawsey, S.M., Hawk, E.T., Qiao, Y.L., Kirsch, I.R. Cancer Res. (2006) [Pubmed]
  26. Effectiveness of selenium supplements in a low-selenium area of China. Xia, Y., Hill, K.E., Byrne, D.W., Xu, J., Burk, R.F. Am. J. Clin. Nutr. (2005) [Pubmed]
  27. Selenium compounds have disparate abilities to impose oxidative stress and induce apoptosis. Stewart, M.S., Spallholz, J.E., Neldner, K.H., Pence, B.C. Free Radic. Biol. Med. (1999) [Pubmed]
  28. The crystal structure of Rv1347c, a putative antibiotic resistance protein from Mycobacterium tuberculosis, reveals a GCN5-related fold and suggests an alternative function in siderophore biosynthesis. Card, G.L., Peterson, N.A., Smith, C.A., Rupp, B., Schick, B.M., Baker, E.N. J. Biol. Chem. (2005) [Pubmed]
  29. Differential effects of naturally occurring and synthetic organoselenium compounds on biomarkers in androgen responsive and androgen independent human prostate carcinoma cells. Pinto, J.T., Sinha, R., Papp, K., Facompre, N.D., Desai, D., El-Bayoumy, K. Int. J. Cancer (2007) [Pubmed]
  30. Selenomethionine induces sustained ERK phosphorylation leading to cell-cycle arrest in human colon cancer cells. Goulet, A.C., Chigbrow, M., Frisk, P., Nelson, M.A. Carcinogenesis (2005) [Pubmed]
  31. Structure of interleukin 1 alpha at 2.7-A resolution. Graves, B.J., Hatada, M.H., Hendrickson, W.A., Miller, J.K., Madison, V.S., Satow, Y. Biochemistry (1990) [Pubmed]
  32. Protein expression systems for structural genomics and proteomics. Yokoyama, S. Current opinion in chemical biology. (2003) [Pubmed]
  33. Crystal structure of the avilamycin resistance-conferring methyltransferase AviRa from Streptomyces viridochromogenes. Mosbacher, T.G., Bechthold, A., Schulz, G.E. J. Mol. Biol. (2003) [Pubmed]
  34. Structure of the mammalian CoA transferase from pig heart. Bateman, K.S., Brownie, E.R., Wolodko, W.T., Fraser, M.E. Biochemistry (2002) [Pubmed]
  35. Determination of selenomethionine and selenocysteine in human serum using speciated isotope dilution-capillary HPLC-inductively coupled plasma collision cell mass spectrometry. Encinar, J.R., Schaumlöffel, D., Ogra, Y., Lobinski, R. Anal. Chem. (2004) [Pubmed]
  36. Methionine changes in bacteriorhodopsin detected by FTIR and cell-free selenomethionine substitution. Bergo, V., Mamaev, S., Olejnik, J., Rothschild, K.J. Biophys. J. (2003) [Pubmed]
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