Amino Acids

, Volume 41, Issue 1, pp 29–41 | Cite as

Chemopreventive mechanisms of α-keto acid metabolites of naturally occurring organoselenium compounds

  • John T. Pinto
  • Jeong-In Lee
  • Raghu Sinha
  • Melanie E. MacEwan
  • Arthur J. L. Cooper
Review Article

Abstract

Previous studies on the chemopreventive mechanisms of dietary selenium have focused on its incorporation into antioxidative selenoproteins, such as glutathione peroxidase and thioredoxin reductase. Several studies, however, have revealed that dietary selenium in the form of l-selenomethionine and the 21st amino acid, selenocysteine, also have intrinsic anti-cancer properties. Biochemical mechanisms previously investigated to contribute to their anticancer effects involve β- and γ-lyase reactions. Some pyridoxal 5′-phosphate (PLP)-containing enzymes can catalyze a β-lyase reaction with Se-methyl-l-selenocysteine (MSC) generating pyruvate and ammonia. Other PLP-enzymes can catalyze a γ-lyase reaction with l-selenomethionine (SM) generating α-ketobutyrate and ammonia. In both cases, a purported third product is methylselenol (CH3SeH). Although not directly quantifiable, as a result of its extreme hydrophobicity and high vapor pressure, CH3SeH has been indirectly observed to act through the alteration of protein-sulfhydryl moieties on redox-responsive signal and transcription factors, thereby maintaining a non-proliferative intracellular environment. We have considered the possibility that α-keto acid analogues of MSC (i.e., methylselenopyruvate; MSP) and SM (i.e., α-keto-γ-methylselenobutyrate; KMSB), generated via a transamination and/or l-amino acid oxidase reaction may also be chemoprotective. Indeed, these compounds were shown to increase the level of histone-H3 acetylation in human prostate and colon cancer cells. MSP and KMSB structurally resemble butyrate, an inhibitor of several histone deacetylases. Thus, the seleno α-keto acid metabolites of MSC and SM, along with CH3SeH derived from β- and γ-lyase reactions, may be potential direct-acting metabolites of organoselenium that lead to de-repression of silenced tumor suppressor proteins and/or regulation of genes and signaling molecules.

Keywords

Prostate cancer Se-Methyl-l-selenocysteine l-Selenomethionine Histone deacetylase Methylselenopyruvate α-Keto-γ-methylselenobutyrate Glutamine transaminase K Glutamine transaminase L l-Amino acid oxidase 

Abbreviations

DMDSe

Dimethyldiselenide

KMSB

α-Keto-γ-methylselenobutyrate

GTK

Glutamine transaminase K

GTL

Glutamine transaminase L

HDAC

Histone deacetylase

LAAO

l-Amino acid oxidase

MSC

Se-Methyl-l-selenocysteine

MSA

Methylseleninic acid

MSP

β-Methylselenopyruvate

NaB

Sodium butyrate

PBS

Phosphate buffered saline

PLP

Pyridoxal 5′-phosphate

PMP

Pyridoxamine 5′-phosphate

SM

l-Selenomethionine

References

  1. Blarzino C, Coccia R, Pensa B, Cini C, De Marco C (1994) Selenomethionine as substrate for glutamine transaminase. Biochem Mol Biol Int 32:79–86PubMedGoogle Scholar
  2. Bolden JE, Peart MJ, Johnstone RW (2006) Anticancer activities of histone deacetylase inhibitors. Nat Rev Drug Discov 5:769–784PubMedCrossRefGoogle Scholar
  3. Boulland ML, Marquet J, Molinier-Frenkel V, Möller P, Guiter C, Lasoudris F, Copie-Bergman C, Baia M, Gaulard P, Leroy K, Castellano F (2007) Human IL4I1 is a secreted l-phenylalanine oxidase expressed by mature dendritic cells that inhibits T-lymphocyte proliferation. Blood 110:220–227PubMedCrossRefGoogle Scholar
  4. Buggy JJ, Sideris ML, Mak P, Lorimer DD, McIntosh B, Clark JM (2000) Cloning and characterization of a novel human histone deacetylase, HDAC8. Biochem J 350:199–205PubMedCrossRefGoogle Scholar
  5. Carbonnelle-Puscian A, Copie-Bergman C, Baia M, Martin-Garcia N, Allory Y, Haioun C, Crémades A, Abd-Alsamad I, Farcet JP, Gaulard P, Castellano F, Molinier-Frenkel V (2009) The novel immunosuppressive enzyme IL4I1 is expressed by neoplastic cells of several B-cell lymphomas and by tumor-associated macrophages. Leukemia 23:952–960PubMedCrossRefGoogle Scholar
  6. Cavallini D, De Marco C, Moldovi B, Mori BG (1960) The cleavage of cystine by cystathionase and the transsulfuration of hypotaurine. Enzymologia 22:161–173PubMedGoogle Scholar
  7. Chen Y, Maret W (2001) Catalytic selenols couple the redox cycles of metallothionein and glutathione. Eur J Biochem 268:3346–3353PubMedCrossRefGoogle Scholar
  8. Chen YC, Sosnoski DM, Gandhi UH, Novinger LJ, Prabhu KS, Mastro AM (2009) Selenium modifies the osteoblast inflammatory stress response to bone metastatic breast cancer. Carcinogenesis 30:1941–1948PubMedCrossRefGoogle Scholar
  9. Clark JP, Cooper CS (2009) ETS gene fusions in prostate cancer. Nat Rev Urol 6:429–439PubMedCrossRefGoogle Scholar
  10. Clark LC, Combs GF Jr, Turnbull BW, Slate EH, Chalker DK, Chow J, Davis LS, Glover RA, Graham GF, Gross EG, Krongrad A, Lesher JL Jr, Park HK, Sanders BB Jr, Smith CL, Taylor JR (1996) Effects of selenium supplementation for cancer prevention in patients with carcinoma of the skin A randomized controlled trial. Nutritional Prevention of Cancer Study Group. JAMA 276:1957–1963PubMedCrossRefGoogle Scholar
  11. Combs GF Jr (2004) Status of selenium in prostate cancer prevention. Br J Cancer 91:195–199PubMedGoogle Scholar
  12. Commandeur JNM, Andreadou I, Rooseboom M, Out M, de Leur LJ, Groot E, Vermeulen NPE (2000) Bioactivation of selenocysteine Se-conjugates by a highly purified rat renal cysteine conjugate β-lyase/glutamine transaminase K. J Pharmacol Exp Ther 294:753–761PubMedGoogle Scholar
  13. Cooper AJL (1988) Glutamine aminotransferases and ω-amidases. In: Kvamme E (ed) Glutamine and glutamate in mammals. CRC Press, Boca Raton, pp 33–52Google Scholar
  14. Cooper AJL (1998) Mechanisms of cysteine S-conjugate β-lyases. Adv Enzymol Relat Areas Mol Biol 72:199–238PubMedGoogle Scholar
  15. Cooper AJL (2004) The role of glutamine transaminase K (GTK) in sulfur and α-keto acid metabolism in the brain, and in the possible bioactivation of neurotoxicants. Neurochem Int 44:557–577PubMedCrossRefGoogle Scholar
  16. Cooper AJL, Anders MW (1990) Glutamine transaminase K and cysteine conjugate β-lyase. Ann N Y Acad Sci 585:118–127PubMedCrossRefGoogle Scholar
  17. Cooper AJL, Meister A (1981) Comparative studies of glutamine transaminases from rat tissues. Comp Biochem Physiol 69B:137–145Google Scholar
  18. Cooper AJL, Pinto JT (2005) Aminotransferase, l-amino acid oxidase and β-lyase reactions involving l-cysteine S-conjugates found in allium extracts. Relevance to biological activity? Biochem Pharmacol 69:209–220PubMedCrossRefGoogle Scholar
  19. Cooper AJL, Pinto JT, Krasnikov BF, Niatsetskaya ZV, Han Q, Li J, Vauzour D, Spencer JPE (2008) Substrate specificity of human glutamine transaminase K as an aminotransferase and as a cysteine S-conjugate β-lyase. Arch Biochem Biophys 474:72–81PubMedCrossRefGoogle Scholar
  20. Dokmanovic M, Clarke C, Marks PA (2007) Histone deacetylase inhibitors: overview and perspectives. Mol Cancer Res 5:981–989PubMedCrossRefGoogle Scholar
  21. Duffield-Lillico AJ, Dalkin BL, Reid ME, Turnbull BW, Slate EH, Jacobs ET, Marshall JR, Clark LC; Nutritional Prevention of Cancer Study Group (2003) Selenium supplementation, baseline plasma selenium status and incidence of prostate cancer: an analysis of the complete treatment period of the Nutritional Prevention of Cancer Trial. BJU Int 91:608–612Google Scholar
  22. Duley JA, Holmes RS (1976) l-α-Hydroxyacid oxidase isozymes. Purification and molecular properties. Eur J Biochem 63:163–173PubMedCrossRefGoogle Scholar
  23. El-Bayoumy K (2009) The negative results of the SELECT study do not necessarily discredit the selenium-cancer prevention hypothesis. Nutr Cancer 61:285–286PubMedCrossRefGoogle Scholar
  24. Frew AJ, Johnstone RW, Bolden JE (2009) Enhancing the apoptotic and therapeutic effects of HDAC inhibitors. Cancer Lett 280:125–133PubMedCrossRefGoogle Scholar
  25. Ganther HE (1999) Selenium metabolism, selenoproteins and mechanisms of cancer prevention: complexities with thioredoxin reductase. Carcinogenesis 20:1657–1666PubMedCrossRefGoogle Scholar
  26. Gasparian AV, Yao YJ, Lü J, Yemelyanov AY, Lyakh LA, Slaga TJ, Budunova IV (2002) Selenium compounds inhibit IκB kinase (IKK) and nuclear factor-κB (NF-κB) in prostate cancer cells. Mol Cancer Ther 1:1079–1087PubMedGoogle Scholar
  27. Giacinti L, Vici P, Lopez M (2008) Epigenome: a new target in cancer therapy. Clin Ter 159:347–360PubMedGoogle Scholar
  28. Hatfield DL, Gladyshev VN (2009) The Outcome of Selenium and Vitamin E Cancer Prevention Trial (SELECT) reveals the need for better understanding of selenium biology. Mol Interv 9:18–21PubMedCrossRefGoogle Scholar
  29. Huang W, Waknitz M (2009) ETS gene fusions and prostate cancer. Am J Transl Res 1:341–351PubMedGoogle Scholar
  30. Huber RE, Criddle RS (1967) Comparison of the chemical properties of selenocysteine and selenocystine with their sulfur analogs. Arch Biochem Biophys 122:164–173PubMedCrossRefGoogle Scholar
  31. Insinga A, Monestiroli S, Ronzoni S, Gelmetti V, Marchesi F, Viale A, Altucci L, Nervi C, Minucci S, Pelicci PG (2005) Inhibitors of histone deacetylases induce tumor-selective apoptosis through activation of the death receptor pathway. Nat Med 11:71–76PubMedCrossRefGoogle Scholar
  32. Ip C (1998) Lessons from basic research in selenium and cancer prevention. J Nutr 128:1845–1854PubMedGoogle Scholar
  33. Ip C, Thompson HJ, Shu Z, Ganther HE (2000) In vitro and in vivo studies of methylseleninic acid: evidence that a monomethylated selenium metabolite is critical for cancer chemoprevention. Cancer Res 60:2882–2886PubMedGoogle Scholar
  34. Jiang C, Wang Z, Ganther H, Lü J (2002) Distinct effects of methylseleninic acid versus selenite on apoptosis, cell cycle, and protein kinase pathways in DU145 human prostate cancer cells. Mol Cancer Ther 1:1059–1066PubMedGoogle Scholar
  35. Keppler BR, Archer TK (2008) Chromatin-modifying enzymes as therapeutic targets—Part 2. Expert Opin Ther Targets 12:1457–1467PubMedCrossRefGoogle Scholar
  36. Klein EA, Thompson IM, Lippman SM, Goodman PJ, Albanes D, Taylor PR, Coltman C (2001) SELECT: the next prostate cancer prevention trial Selenum and Vitamin E Cancer Prevention Trial. J Urol 166:1311–1315PubMedCrossRefGoogle Scholar
  37. Klein EA, Thompson IM, Lippman SM, Goodman PJ, Albanes D, Taylor PR, Coltman C (2003) SELECT: the selenium and vitamin E cancer prevention trial. Urol Oncol 21:59–65PubMedCrossRefGoogle Scholar
  38. Laclaustra M, Navas-Acien A, Stranges S, Ordovas JM, Guallar E (2009) Serum selenium concentrations, diabetes in U.S. adults: National Health, Nutrition Examination Survey (NHANES) 2003–2004. Environ Health Perspect 117:1409–1413PubMedGoogle Scholar
  39. Lane AA, Chabner BA (2009) Histone deacetylase inhibitors in cancer therapy. J Clin Oncol 27:5459–5468PubMedCrossRefGoogle Scholar
  40. Lee JI, Nian H, Cooper AJL, Sinha R, Dai J, Bisson WH, Dashwood RH, Pinto JT (2009) α-Keto acid metabolites of naturally occurring organoselenium compounds as inhibitors of histone deacetylase in human prostate cancer cells. Cancer Prev Res 2:683–693CrossRefGoogle Scholar
  41. Li GX, Lee HJ, Wang Z, Hu H, Liao JD, Watts JC, Combs GF Jr, Lü J (2008) Superior in vivo inhibitory efficacy of methylseleninic acid against human prostate cancer over selenomethionine or selenite. Carcinogenesis 29:1005–1012PubMedCrossRefGoogle Scholar
  42. Lichtenberg LA, Wellner D (1968) A sensitive fluorometric assay for amino acid oxidase. Anal Biochem 26:313–319PubMedCrossRefGoogle Scholar
  43. Lillig CH, Holmgren A (2007) Thioredoxin and related molecules—from biology to health and disease. Antioxid Redox Signal 9:25–47PubMedCrossRefGoogle Scholar
  44. Lippman SM, Goodman PJ, Klein EA, Parnes HL, Thompson IM Jr, Kristal AR, Santella RM, Probstfield JL, Moinpour CM, Albanes D, Taylor PR, Minasian LM, Hoque A, Thomas SM, Crowley JJ, Gaziano JM, Stanford JL, Cook ED, Fleshner NE, Lieber MM, Walther PJ, Khuri FR, Karp DD, Schwartz GG, Ford LG, Coltman CA Jr (2005) Designing the Selenium and Vitamin E Cancer Prevention Trial (SELECT). J Natl Cancer Inst 97:94–102PubMedCrossRefGoogle Scholar
  45. Lippman SM, Klein EA, Goodman PJ, Lucia MS, Thompson IM, Ford LG, Parnes HL, Minasian LM, Gaziano JM, Hartline JA, Parsons JK, Bearden JD 3rd, Crawford ED, Goodman GE, Claudio J, Winquist E, Cook ED, Karp DD, Walther P, Lieber MM, Kristal AR, Darke AK, Arnold KB, Ganz PA, Santella RM, Albanes D, Taylor PR, Probstfield JL, Jagpal TJ, Crowley JJ, Meyskens FL Jr, Baker LH, Coltman CA Jr (2009) Effect of selenium and vitamin E on risk of prostate cancer and other cancers: The Selenium and Vitamin E Cancer Prevention Trial (SELECT). JAMA 301:39–51PubMedCrossRefGoogle Scholar
  46. Liu P, Li S, Gan L, Kao TP, Huang H (2008) A transcription-independent function of FOXO1 in inhibition of androgen-independent activation of the androgen receptor in prostate cancer cells. Cancer Res 68:10290–10299PubMedCrossRefGoogle Scholar
  47. Lu J, Jiang C (2001) Antiangiogenic activity of selenium in cancer chemoprevention: metabolite-specific effects. Nutr Cancer 40:64–73PubMedCrossRefGoogle Scholar
  48. Marks PA, Xu WS (2009) Histone deacetylase inhibitors: Potential in cancer therapy. J Cell Biochem 107:600–608PubMedCrossRefGoogle Scholar
  49. Mason JM, Naidu MD, Barcia M, Porti D, Chavan SS, Chu CC (2004) IL-4-induced gene-1 is a leukocyte l-amino acid oxidase with an unusual acidic pH preference and lysosomal localization. J Immunol 173:4561–4567PubMedGoogle Scholar
  50. Meister A, Sober HA, Tice SV, Fraser PE (1952) Transamination and associated deamidation of asparagine and glutamine. J Biol Chem 197:319–330PubMedGoogle Scholar
  51. Moeller T (1963) Inorganic chemistry: an advanced textbook. Wiley, New York, p 135Google Scholar
  52. Myzak MC, Karplus PA, Chung FL, Dashwood RH (2004) A novel mechanism of chemoprotection by sulforaphane: inhibition of histone deacetylase. Cancer Res 64:5767–5774PubMedCrossRefGoogle Scholar
  53. Nagaoka K, Aoki F, Hayashi M, Muroi Y, Sakurai T, Itoh K, Ikawa M, Okabe M, Imakawa K, Sakai S (2009) l-Amino acid oxidase plays a crucial role in host defense in the mammary glands. FASEB J 23:2514–2520PubMedCrossRefGoogle Scholar
  54. Nian H, Delage B, Pinto JT, Dashwood RH (2008) Allyl mercaptan, a garlic-derived organosulfur compound, inhibits histone deacetylase and enhances Sp3 binding on the P21WAF1 promoter. Carcinogenesis 29:1816–1824PubMedCrossRefGoogle Scholar
  55. Nian H, Delage B, Ho E, Dashwood RH (2009a) Modulation of histone deacetylase activity by dietary isothiocyanates and allyl sulfides: studies with sulforaphane and garlic organosulfur compounds. Environ Mol Mutagen 50:213–221PubMedCrossRefGoogle Scholar
  56. Nian H, Bisson WH, Dashwood W-M, Pinto JT, Dashwood RH (2009b) α-Keto acid metabolites of organoselenium compounds inhibit histone deacetylase activity in human colon cancer cells. Carcinogenesis 30:1416–1423PubMedCrossRefGoogle Scholar
  57. Ohta Y, Kobayashi Y, Konishi S, Hirano S (2009) Speciation analysis of selenium metabolites in urine and breath by HPLC- and GC-inductively coupled plasma-MS after administration of selenomethionine and methylselenocysteine to rats. Chem Res Toxicol 22:1795–1801PubMedCrossRefGoogle Scholar
  58. Okuno T, Motobayashi S, Ueno H, Nakamuro K (2005) Identification of mouse selenomethionine α, γ-elimination enzyme: cystathionine γ-lyase catalyzes its reaction to generate methylselenol. Biol Trace Elem Res 108:245–257PubMedCrossRefGoogle Scholar
  59. Papp LV, Lu J, Holmgren A, Khanna KK (2007) From selenium to selenoproteins: synthesis, identity, and their role in human health. Antioxid Redox Signal 9:775–806PubMedCrossRefGoogle Scholar
  60. Pinto JT, Sinha R, Papp K, Facompre ND, Desai D, El-Bayoumy K (2007) Differential effects of naturally occurring and synthetic organoselenium compounds on biomarkers in androgen responsive and androgen independent human prostate carcinoma cells. Int J Cancer 120:1410–1417PubMedCrossRefGoogle Scholar
  61. Puccetti E, Obradovic D, Beissert T, Bianchini A, Washburn B, Chiaradonna F, Boehrer S, Hoelzer D, Ottmann OG, Pelicci PG, Nervi C, Ruthardt M (2002) AML-associated translocation products block vitamin D3-induced differentiation by sequestering the vitamin D3 receptor. Cancer Res 62:7050–7058PubMedGoogle Scholar
  62. Ravn-Haren G, Krath BN, Overvad K, Cold S, Moesgaard S, Larsen EH, Dragsted LO (2007) Effect of long-term selenium yeast intervention on activity and gene expression of antioxidant and xenobiotic metabolizing enzymes in healthy elderly volunteers from the Danish Prevention of Cancer by Intervention by Selenium (PRECISE) pilot study. Br J Nutr 99:1190–1198PubMedGoogle Scholar
  63. Richon VM, Sandhoff TW, Rifkind RA, Marks PA (2000) Histone deacetylase inhibitor selectively induces p21WAF1 expression and gene-associated histone acetylation. Proc Natl Acad Sci USA 97:10014–10019PubMedCrossRefGoogle Scholar
  64. Rooseboom M, Vermeulen NPE, Durgut F, Commandeur JNM (2002) Comparative study on the bioactivation mechanisms and cytotoxicity of Te-phenyl-l-tellurocysteine, Se-phenyl-l-selenocysteine, and S-phenyl-l-cysteine. Chem Res Toxicol 15:1610–1618PubMedCrossRefGoogle Scholar
  65. Rudolf E, Králová V, Cervinka M (2008) Selenium and colon cancer—from chemoprevention to new treatment modality. Anticancer Agents Med Chem 8:598–602PubMedGoogle Scholar
  66. Sanmartín C, Plano D, Palop JA (2008) Selenium compounds and apoptotic modulation: a new perspective in cancer therapy. Mini Rev Med Chem 8:1020–1031PubMedCrossRefGoogle Scholar
  67. Scher HI, Mazumdar M, Kelly WK (1996) Clinical trials in relapsed prostate cancer: Defining the target. J Natl Canc Inst 88:1623–1634CrossRefGoogle Scholar
  68. Shah RB, Mehra R, Chinnaiyan AM, Shen R, Ghosh D, Zhou M, Macvicar GR, Varambally S, Harwood J, Bismar TA, Kim R, Rubin MA, Pienta KJ (2004) Androgen-independent prostate cancer is a heterogeneous group of diseases: lessons from a rapid autopsy program. Cancer Res 64:9209–9216PubMedCrossRefGoogle Scholar
  69. Shankar S, Srivastava RK (2008) Histone deacetylase inhibitors: mechanisms and clinical significance in cancer: HDAC inhibitor-induced apoptosis. Adv Exp Med Biol 615:261–298PubMedCrossRefGoogle Scholar
  70. Singh U, Null K, Sinha R (2008) In vitro growth inhibition of mouse mammary epithelial tumor cells by methylseleninic acid: involvement of protein kinases. Mol Nutr Food Res 52:1281–1288PubMedCrossRefGoogle Scholar
  71. Sinha R, El-Bayoumy K (2004) Apoptosis is a critical cellular event in cancer chemoprevention and chemotherapy by selenium compounds. Curr Cancer Drug Targets 4:13–28PubMedCrossRefGoogle Scholar
  72. Sinha R, Pinto JT, Facompre N, Kilheffer J, Baatz JE, El-Bayoumy K (2008) Effects of naturally occurring and synthetic organoselenium compounds on protein profiling in androgen responsive and androgen independent human prostate cancer cells. Nutr Cancer 60:267–275PubMedCrossRefGoogle Scholar
  73. Sinha R, Sinha I, Null K, King T, Wolter W, Suckow M (2009) Methylseleninic acid inhibits HIF-1α in hormone refractory prostate cancer. [Abstract]. In: Proceedings of the 100th Annual Meeting of the American Association for Cancer Research; 18–22 April 2009, Denver, CO. AACR, Philadelphia (Abstract # 5583)Google Scholar
  74. Spallholz JE, Shriver BJ, Reid TW (2001) Dimethyldiselenide and methylseleninic acid generate superoxide in an in vitro chemiluminescence assay in the presence of glutathione: implications for the anticarcinogenic activity of l-selenomethionine and l-Se-methylselenocysteine. Nutr Cancer 40:34–41PubMedCrossRefGoogle Scholar
  75. Stevens JL, Robbins JD, Byrd RA (1986) A purified cysteine conjugate β-lyase from rat kidney cytosol Requirement for an α-keto acid or an amino acid oxidase for activity and identity with soluble glutamine transaminase K. J Biol Chem 261:15529–15537PubMedGoogle Scholar
  76. Sun Y, Nonobe E, Kobayashi Y, Kuraishi T, Aoki F, Yamamoto K, Sakai S (2002) Characterization and expression of l-amino acid oxidase of mouse milk. J Biol Chem 277:19080–19086PubMedCrossRefGoogle Scholar
  77. Suzana S, Cham BG, Ahmad Rohi G, Mohd Rizal R, Fairulnizal MN, Normah H, Fatimah A (2009) Relationship between selenium and breast cancer: a case-control study in the Klang Valley. Singapore Med J 50:265–269PubMedGoogle Scholar
  78. Suzuki KT, Tsuji Y, Ohta Y, Suzuki N (2008) Preferential organ distribution of methylselenol source Se-methylselenocysteine relative to methylseleninic acid. Toxicol Appl Pharmacol 227:76–83PubMedCrossRefGoogle Scholar
  79. Tsuji Y, Suzuki N, T Suzuki K, Ogra Y (2009) Selenium metabolism in rats with long-term ingestion of Se-methylselenocysteine using enriched stable isotopes. J Toxicol Sci 34:191–200Google Scholar
  80. Ungerstedt JS, Sowa Y, Xu WS, Shao Y, Dokmanovic M, Perez G, Ngo L, Holmgren A, Jiang X, Marks PA (2005) Role of thioredoxin in the response of normal and transformed cells to histone deacetylase inhibitors. Proc Natl Acad Sci USA 102:673–678PubMedCrossRefGoogle Scholar
  81. Unni E, Koul D, Yung W-K, Sinha R (2005) Se-methylselenocysteine inhibits phosphatidylinositol 3-kinase activity of mouse mammary epithelial tumor cells in vitro. Breast Cancer Res 7:R699–R707PubMedCrossRefGoogle Scholar
  82. Vanommeslaeghe K, Loverix S, Geerlings P, Tourwé D (2005) DFT-based ranking of zinc-binding groups in histone deacetylase inhibitors. Bioorg Med Chem 13:6070–6082PubMedCrossRefGoogle Scholar
  83. Venkateswaran V, Klotz LH, Fleshner NE (2002) Selenium modulation of cell proliferation and cell cycle biomarkers in human prostate carcinoma cell lines. Cancer Res 62:2540–2545PubMedGoogle Scholar
  84. Vigushin DM, Coombes RC (2004) Targeted histone deacetylase inhibition for cancer therapy. Curr Cancer Drug Targets 4:205–218PubMedCrossRefGoogle Scholar
  85. Wang Z, Jiang C, Lu J (2002) Induction of caspase-mediated apoptosis and cell-cycle G1 arrest by selenium metabolite methylselenol. Mol Carcinog 34:113–120PubMedCrossRefGoogle Scholar
  86. Wang LG, Liu XM, Fang Y, Dai W, Chiao FB, Puccio GM, Feng J, Liu D, Chiao JW (2008) De-repression of the p21 promoter in prostate cancer cells by an isothiocyanate via inhibition of HDACs and c-Myc. Int J Oncol 33:375–380PubMedGoogle Scholar
  87. Wang L, Zou X, Berger AD, Twiss C, Peng Y, Li Y, Chiu J, Guo H, Satagopan J, Wilton A, Gerald W, Basch R, Wang Z, Osman I, Lee P (2009) Increased expression of histone deacetylases (HDACs) and inhibition of prostate cancer growth and invasion by HDAC inhibitor SAHA. Am J Transl Res 1:62–71PubMedGoogle Scholar
  88. Welsbie DS, Xu J, Chen Y, Borsu L, Scher HI, Rosen N, Sawyers CL (2009) Histone deacetylases are required for androgen receptor function in hormone-sensitive and castrate-resistant prostate cancer. Cancer Res 69:958–966PubMedCrossRefGoogle Scholar
  89. Wessjohann LA, Schneider A, Abbas M, Brandt W (2007) Selenium in chemistry and biochemistry in comparison to sulfur. Biol Chem 388:997–1006PubMedCrossRefGoogle Scholar
  90. Whanger PD (2004) Selenium and its relationship to cancer: an update. Br J Nutr 91:11–28PubMedCrossRefGoogle Scholar
  91. Xiong SD, Yu K, Liu XH, Yin LH, Kirschenbaum A, Yao S, Narla G, DiFeo A, Wu JB, Yuan Y, Ho SM, Lam YW, Levine AC (2009) Ribosome-inactivating proteins isolated from dietary bitter melon induce apoptosis and inhibit histone deacetylase-1 selectively in premalignant and malignant prostate cancer cells. Int J Cancer 125:774–782 (Erratum in: Int J Cancer (2009) 125:1995)Google Scholar
  92. Xu WS, Parmigiani RB, Marks PA (2007) Histone deacetylase inhibitors: molecular mechanisms of action. Oncogene 26:5541–5552PubMedCrossRefGoogle Scholar
  93. Yang Y, Hou H, Haller EM, Nicosia SV, Bai W (2005) Suppression of FOXO1 activity by FHL2 through SIRT1-mediated deacetylation. EMBO J 24:1021–1032PubMedCrossRefGoogle Scholar
  94. Zeng H, Wu M, Botnen JH (2009) Methylselenol, a selenium metabolite, induces cell cycle arrest in G1 phase and apoptosis via the extracellular-regulated kinase 1/2 pathway and other cancer signaling genes. J Nutr 139:1613–1618PubMedCrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  • John T. Pinto
    • 1
  • Jeong-In Lee
    • 1
  • Raghu Sinha
    • 2
  • Melanie E. MacEwan
    • 1
  • Arthur J. L. Cooper
    • 1
  1. 1.Department of Biochemistry and Molecular BiologyNew York Medical CollegeValhallaUSA
  2. 2.Department of Biochemistry and Molecular BiologyPenn State College of MedicineHersheyUSA

Personalised recommendations