α-Keto acid metabolites of naturally occurring organoselenium compounds as inhibitors of histone deacetylase in human prostate cancer cells

Cancer Prevention Research

Volumn 2, Issue 7, 2009, Pages 683-693

  Lee, Jeong In ^a   Nian, Hui ^b   Cooper, Arthur J L ^a   Sinha, Raghu ^c   Dai, Jenny ^c   Bisson, William H ^b   Dashwood, Roderick H ^b   Pinto, John Thomas ^a  

^a NEW YORK MEDICAL COLLEGE   (United States)

^b OREGON STATE UNIVERSITY   (United States)

^c PENN STATE COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXOACID; ALPHA KETO GAMMA METHYLSELENOBUTYRIC ACID; AMINO ACID OXIDASE; BETA METHYLSELENOPYRUVIC ACID; BUTYRIC ACID; GLUTAMINE PHENYLPYRUVATE AMINOTRANSFERASE; HISTONE DEACETYLASE INHIBITOR; HISTONE H3; METHIONINE; SELENIUM DERIVATIVE; SELENOCYSTEINE; SELENOMETHIONINE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CANCER CELL; CONTROLLED STUDY; DRUG METABOLISM; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SUBSTRATE; HUMAN; HUMAN CELL; MALE; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; PRIORITY JOURNAL; PROSTATE CANCER; PROTEIN EXPRESSION; RAT; STRUCTURAL HOMOLOGY;

CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HISTONE DEACETYLASES; HISTONES; HUMANS; INHIBITORY CONCENTRATION 50; KETO ACIDS; L-AMINO ACID OXIDASE; LYASES; MALE; MASS SPECTROMETRY; METHIONINE; PROSTATIC NEOPLASMS; PROTEIN PROCESSING, POST-TRANSLATIONAL; SELENIUM; TRANSAMINASES;

EID: 69249166677     PISSN: 19406207     EISSN: None     Source Type: Journal    
DOI: 10.1158/1940-6207.CAPR-09-0047     Document Type: Article

References (60)

1. ACS, Cancer facts and figures 2009.
2. Willett WC, Polk BF, Morris JS, et al. Prediagnostic serum selenium and risk of cancer. Lancet 1983;2:130-134
3. Clark LC, Alberts DS. Selenium and cancer: risk or protection? J Natl Cancer Inst 1995;87:497-505.
4. Nyman DW, Suzanne Stratton M, Kopplin MJ, Dalkin BL, Nagle RB, Jay Gandolfi A. Selenium and selenomethionine levels in prostate cancer patients. Cancer Detect Prev 2004;28:8-16. (Pubitemid 39403828)
5. Brooks JD, Metter EJ, Chan DW, et al. Plasma selenium level before diagnosis and the risk of prostate cancer development. J Urol 2001;166:2034-2038
6. Clark LC, Combs GF, Jr., Turnbull BW, et al. 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 1996;276:1957-1963
7. Duffield-Lillico AJ, Reid ME, Turnbull BW, et al. Baseline characteristics and the effect of selenium supplementation on cancer incidence in a randomized clinical trial: a summary report of the Nutritional Prevention of Cancer Trial. Cancer Epidemiol Biomarkers Prev 2002;11:630-639
8. Lippman SM, Klein EA, Goodman PJ, et al. Effect of selenium and vitamin E on risk of prostate cancer and other cancers: the Selenium and Vitamin E Cancer Prevention Trial (SELECT). JAMA 2009;301:39-51.
9. Tsavachidou D, McDonnell TJ, Wen S, et al. Selenium and vitamin E: cell type- and intervention-specific tissue effects in prostate cancer. J Natl Cancer Inst 2009;101:306-320
10. Pinto JT, Sinha R, Papp K, Facompre ND, Desai D, El-Bayoumy K. Differential effects of naturally occurring and synthetic organoselenium compounds on biomarkers in androgen responsive and androgen independent human prostate carcinoma cells. Int J Cancer 2007;120:1410-1417 (Pubitemid 46355374)
11. Dong Y, Lisk D, Block E, Ip C. Characterization of the biological activity of γ-glutamyl-Se-methylselenocysteine: a novel, naturally occurring anticancer agent from garlic. Cancer Res 2001;61:2923-2928 (Pubitemid 32691936)
12. Lyi SM, Heller LI, Rutzke M, Welch RM, Kochian LV, Li L. Molecular and biochemical characterization of the selenocysteine Se-methyltransferase gene and Se-methylselenocysteine synthesis in broccoli. Plant Physiol 2005;138:409-420 (Pubitemid 43138139)
13. Johnson WD, Morrissey RL, Kapetanovic I, Crowell JA, McCormick DL. Subchronic oral toxicity studies of Se-methylselenocysteine, an organoselenium compound for breast cancer prevention. Food Chem Toxicol 2008;46:1068-1078
14. El-Bayoumy K, Sinha R. Mechanisms of mammary cancer chemoprevention by organoselenium compounds. Mutat Res 2004;551:181-197
15. Medina D, Thompson H, Ganther H, Ip C. Semethylselenocysteine: a new compound for chemoprevention of breast cancer. Nutr Cancer 2001;40:12-17 (Pubitemid 34037509)
16. Ip C, Dong Y. Methylselenocysteine modulates proliferation and apoptosis biomarkers in premalignant lesions of the rat mammary gland. Anticancer Res 2001;21:863-867 (Pubitemid 32494181)
17. Unni E, Koul D, Yung WK, Sinha R. Se-methylselenocysteine inhibits phosphatidylinositol 3-kinase activity of mouse mammary epithelial tumor cells in vitro. Breast Cancer Res 2005;7:R699-707.
18. Sinha R, Kiley SC, Lu JX, et al. Effects of methylselenocysteine on PKC activity, cdk2 phosphorylation and gad gene expression in synchronized mouse mammary epithelial tumor cells. Cancer Lett 1999;146:135-145 (Pubitemid 29492882)
19. Ip C, Ganther HE. Comparison of selenium and sulfur analogs in cancer prevention. Carcinogenesis 1992;13:1167-1170
20. Lee SO, Yeon Chun J, Nadiminty N, et al. Monomethylated selenium inhibits growth of LNCaP human prostate cancer xenograft accompanied by a decrease in the expression of androgen receptor and prostate-specific antigen (PSA). Prostate 2006;66:1070-1075 (Pubitemid 43939210)
21. Spallholz JE, Shriver BJ, Reid TW. 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 2001;40:34-41.
22. Cooper AJL, Pinto JT. Aminotransferase, L-amino acid oxidase and β-lyase reactions involving L-cysteine S-conjugates found in allium extracts. Relevance to biological activity? Biochem Pharmacol 2005;69:209-220
23. Stevens JL, Robbins JD, Byrd RA. 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 1986;261:15529-15537
24. Cooper AJL. Mechanisms of cysteine S-conjugate β-lyases. Adv Enzymol Relat Areas Mol Biol 1998;72:199-238.
25. Commandeur JNM, Andreadou I, Rooseboom M, et al. Bioactivation of selenocysteine Se-conjugates by a highly purified rat renal cysteine conjugate β-lyase/glutamine transaminase K. J Pharmacol Exp Ther 2000;294:753-761 (Pubitemid 30490854)
26. Cooper AJL. 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 2004;44:557-577
27. Cooper AJL, Pinto JT, Krasnikov BF, et al. Substrate specificity of human glutamine transaminase K as an aminotransferase and as a cysteine S-conjugate β-lyase. Arch Biochem Biophys 2008;474:72-81.
28. Rooseboom M, Vermeulen NPE, Durgut F, Commandeur JNM. 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 2002;15:1610-1618
29. Butler KV, Kozikowski AP. Chemical origins of isoform selectivity in histone deacetylase inhibitors. Curr Pharm Des 2008;14:505-528
30. Insinga A, Monestiroli S, Ronzoni S, et al. Inhibitors of histone deacetylases induce tumor-selective apoptosis through activation of the death receptor pathway. Nat Med 2005;11:71-76 (Pubitemid 40215840)
31. Xu WS, Parmigiani RB, Marks PA. Histone deacetylase inhibitors: molecular mechanisms of action. Oncogene 2007;26:5541-5552
32. Ungerstedt JS, Sowa Y, Xu WS, et al. Role of thioredoxin in the response of normal and transformed cells to histone deacetylase inhibitors. Proc Natl Acad Sci U S A 2005;102:673-678 (Pubitemid 40282724)
33. Buggy JJ, Sideris ML, Mak P, Lorimer DD, Mcintosh B, Clark JM. Cloning and characterization of a novel human histone deacetylase, HDAC8. Biochem J 2000;350:199-205. (Pubitemid 30681331)
34. Vanommeslaeghe K, Loverix S, Geerlings P, Tourwé D. DFT-based ranking of zinc-binding groups in histone deacetylase inhibitors. Bioorg Med Chem 2005;13:6070-6082 (Pubitemid 41399918)
35. El-Bayoumy K, Narayanan BA, Desai DH, et al. Elucidation of molecular targets of mammary cancer chemoprevention in the rat by organoselenium compounds using cDNA microarray. Carcinogenesis 2003;24:1505-1514 (Pubitemid 37160841)
36. El-Bayoumy K, Chae YH, Upadhyaya P, Meschter C, Cohen LA, Reddy BS. Inhibition of 7,12-dimethylbenz(a)anthracene-induced tumors and DNA adduct formation in the mammary glands of female Sprague-Dawley rats by the synthetic organoselenium compound 1,4-phenylenebis(methylene)selenocyanate. Cancer Res 1992;52:2402-2407
37. Ip C, Lisk DJ, Ganther HE. Activities of structurally-related lipophilic selenium compounds as cancer chemopreventive agents. Anticancer Res 1998;18:4019-4025
38. Han Q, Li J, Li J. pH dependence, substrate specificity and inhibition of human kynurenine aminotransferase I. Eur J Biochem 2004;271:4804-4814 (Pubitemid 40065583)
39. Somoza JR, Skene RJ, Katz BA, et al. Structural snapshots of human HDAC8 provide insights into the class I histone deacetylases. Structure 2004;12:1325-1334
40. Finnin MS, Donigian JR, Cohen A, et al. Structures of a histone deacetylase homologue bound to the TSA and SAHA inhibitors. Nature 1999;401:188-193 (Pubitemid 29436325)
41. Nemethy G, Gibson KD, Palmer KA, Yoon CN, Paterlini MG, Zagari A. Energy parameters in polypeptides. 10. Improved geometrical parameters and non bonded interactions for use in the ECEPP/3 algorithm, with application to proline-containing peptides. J Phys Chem 1992;96:6472-6484
42. Abagyan R, Totrov M, Kuznetsov D. ICM - a new method for protein modeling and design-applications to docking and structure prediction from the distorted native conformation. J Comput Chem 1994;15:488-506.
43. Abagyan R, Totrov M. Biased probability MonteCarlo conformational searches and electrostatic calculations for peptides and proteins. J Mol Biol 2003;235:983-1002.
44. Abagyan R, Totrov M. Ab-initio folding of peptides by the optimal-bias Monte Carlo minimization procedure. J Comput Phys 1999;151:402-421
45. Metropolis N, Rosenbluth AW, Rosenbluth MN, Teller AH, Teller E. Equation of state calculations by fast computing machines. J Chem Phys 1953;21:1087-1092
46. Totrov M, Abagyan R. Protein-ligand docking as an energy optimization problem. In: Raffa RB, editor. Drug-receptor thermodynamics: introduction and experimental application. New York: John Wiley & Sons; 2001, p. 603-624
47. Rossi F, Han Q, Li J, Li J, Rizzi M. Crystal structure of human kynurenine aminotransferase I. J Biol Chem 2004;279:50214-50220 (Pubitemid 39577835)
48. Berman HM, Westbrook J, Feng Z, lype L, Schneider B, Zardecki C. The Protein Data Bank. Nucleic Acids Res 2000;28:235-242
49. Myzak MC, Karplus PA, Chung F-L, Dashwood RH. A novel mechanism of chemoprotection by sulforaphane: inhibition of histone deacetylase. Cancer Res 2004;64:5767-5774 (Pubitemid 39095576)
50. Dashwood RH, Myzak MC, Ho E. Dietary HDAC inhibitors: time to rethink weak ligands in cancer chemoprevention? Carcinogenesis 2006;27:344-349
51. Dashwood RH, Ho E. Dietary histone deacetylase inhibitors: from cells to mice to man. Semin Cancer Biol 2007;17:363-369 (Pubitemid 47369168)
52. Rooseboom M, Commandeur JNM, Floor GC, Rettie AE, Vermeulen NPE. Selenoxidation by flavin-containing monooxygenases as a novel pathway for β-elimination of selenocysteine Seconjugates. Chem Res Toxicol 2001;14:127-134 (Pubitemid 32064381)
53. Hatfield DL, Gladyshev VN. How selenium has altered our understanding of the genetic code. Mol Cell Biol 2002;11:3565-3576
54. Suzuki KT, Tsuji Y, Ohta Y, Suzuki N. Preferential organ distribution of methylselenol source Semethylselenocysteine relative to methylseleninic acid. Toxicol Appl Pharmacol 2008;227:76-83. (Pubitemid 351179845)
55. Medina D, Thompson H, Ganther H, Ip C. SeMethylselenocysteine: a new compound for chemoprevention of breast cancer. Nutr Cancer 2001;40:12-17
56. Ganther HE. Selenium metabolism, selenoproteins and mechanisms of cancer prevention: complexities with thioredoxin reductase. Carcinogenesis 1999;20:1657-1666
57. Cooper AJL, Pinto JT. Role of cysteine S-conjugate β-lyases in the bioactivation of renal toxicants. Biotechnology: pharmaceutical aspects. In: Elfarra AA, editor. Advances in bioactivation research. Springer: New York, NY; 2008, p. 323-346
58. Nian H, Bisson WH, Dashwood W-M, Pinto JT, Dashwood RH. α-Keto acid metabolites of organoselenium compounds inhibit histone deacetylase activity in human colon cancer. Carcinogenesis. In Press, 2009.
59. Esteller M, Almouzni G. How epigenetics integrates nuclear functions. Workshop on epigenetics and chromatin: transcriptional regulation and beyond. EMBO Rep 2005;6:624-628
60. Nian H, Delage B, Pinto JT, Dashwood RH. Allyl mercaptan, a garlic-derived organosulfur compound, inhibits histone deacetylase and enhances Sp3 binding on the P21WAF1 promoter. Carcinogenesis 2008;29:1816-1824