Polyamine analogues targeting epigenetic gene regulation

Essays in Biochemistry

Volumn 46, Issue 1, 2009, Pages 95-110

  Huang, Yi ^a   Marton, Laurence J ^b   Woster, Patrick M ^c   Casero Jr , Robert A ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b Progen Pharmaceuticals   (United States)

^c WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; HISTONE DEACETYLASE; POLYAMINE; RNA;

AMINO ACID SEQUENCE; ANIMAL; BIOLOGICAL MODEL; CHEMICAL MODEL; CHEMISTRY; GENE EXPRESSION REGULATION; GENE SILENCING; GENETIC EPIGENESIS; HUMAN; METABOLISM; MOLECULAR GENETICS; NEOPLASM; REVIEW; SEQUENCE HOMOLOGY;

AMINO ACID SEQUENCE; ANIMALS; DNA; EPIGENESIS, GENETIC; GENE EXPRESSION REGULATION; GENE SILENCING; HISTONE DEACETYLASES; HUMANS; MODELS, BIOLOGICAL; MODELS, CHEMICAL; MOLECULAR SEQUENCE DATA; NEOPLASMS; POLYAMINES; RNA; SEQUENCE HOMOLOGY, AMINO ACID;

EID: 77449090884     PISSN: 00711365     EISSN: None     Source Type: Journal    
DOI: 10.1042/BSE0460007     Document Type: Article

References (43)

1. Casero, Jr, R.A. and Marton, L.J. (2007) Targeting polyamine metabolism and function in cancer and other hyperproliferative diseases. Nat. Rev. Drug Discov. 6, 373-390
2. Wallace, H.M., Fraser, A.V. and Hughes, A. (2003) A perspective of polyamine metabolism. Biochem. J. 376, 1-14
3. Pegg, A.E. (2006) Regulation of ornithine decarboxylase. J. Biol. Chem. 281, 14529-14532
4. Gerner, E.W. and Meyskens, Jr, F.L. (2009) Combination chemoprevention for colon cancer targeting polyamine synthesis and inflammation. Clin. Cancer Res. 15, 758-761
5. Seiler, N. (2005) Pharmacological aspects of cytotoxic polyamine analogs and derivatives for cancer therapy. Pharmacol. Ther. 107, 99-119
6. Basu, H.S., Smirnov, I.V., Peng, H.F., Tiffany, K. and Jackson, V. (1997) Effects of spermine and its cytotoxic analogs on nucleosome formation on topologically stressed DNA in vitro. Eur. J. Biochem. 243, 247-258
7. Basu, H.S., Sturkenboom, M.C., Delcros, J.G., Csokan, P.P., Szollosi, J., Feuerstein, B.G. and Marton, L.J. (1992) Effect of polyamine depletion on chromatin structure in U-87 MG human brain tumour cells. Biochem. J. 282, 723-727
8. Sato, N., Ohtake, Y., Kato, H., Abe, S., Kohno, H. and Ohkubo, Y. (2003) Effects of polyamines on histone polymerization. J. Protein Chem. 22, 303-307
9. Jones, P.A. and Baylin, S.B. (2007) The epigenomics of cancer. Cell 128, 683-692
10. Coffino, P. (2001) Regulation of cellular polyamines by antizyme. Nat. Rev. Mol. Cell Biol. 2, 188-194
11. Pegg, A.E. (2008) Spermidine/spermine-N1-acetyltransferase: a key metabolic regulator. Am. J. Physiol. Endocrinol. Metab. 294, E995-E1010
12. Wang, Y., Devereux, W., Woster, P., Stewart, T., Hacker, A. and Casero, Jr, R. (2001) Cloning and characterization of a human polyamine oxidase that is inducible by polyamine analogue exposure. Cancer Res. 61, 5370-5373
13. Vujcic, S., Diegelman, P., Bacchi, C.J., Kramer, D.L. and Porter, C.W. (2002) Identification and characterization of a novel flavin-containing spermine oxidase of mammalian cell origin. Biochem. J. 367, 665-675
14. Murray-Stewart, T., Wang, Y., Goodwin, A., Hacker, A., Meeker, A. and Casero, Jr, R.A. (2008) Nuclear localization of human spermine oxidase isoforms: possible implications in drug response and disease etiology. FEBS J. 275, 2795-2806
15. Wang, Y., Murray-Stewart, T., Devereux, W., Hacker, A., Frydman, B., Woster, P. and Casero, Jr, R. (2003) Properties of purified recombinant human polyamine oxidase, PAOh1/SMO. Biochem. Biophys. Res. Commun. 304, 605-611
16. Jenuwein, T. and Allis, C.D. (2001) Translating the histone code. Science 293, 1074-1080
17. Kuo, M.H. and Allis, C.D. (1998) Roles of histone acetyltransferases and deacetylases in gene regulation. BioEssays 20, 615-626
18. Shi, Y., Lan, F., Matson, C., Mulligan, P., Whetstine, J., Cole, P., Casero, R. and Shi, Y. (2004) Histone demethylation mediated by the nuclear amine oxidase homolog LSD1. Cell 119, 941-953
19. Klose, R.J., Kallin, E.M. and Zhang, Y. (2006) JmjC-domain-containing proteins and histone demethylation. Nat. Rev. Genet. 7, 715-727
20. Shi, Y. (2007) Histone lysine demethylases: emerging roles in development, physiology and disease. Nat. Rev. Genet. 8, 829-833
21. Holley, J.L., Mather, A., Wheelhouse, R.T., Cullis, P.M., Hartley, J.A., Bingham, J.P. and Cohen, G.M. (1992) Targeting of tumor cells and DNA by a chlorambucil-spermidine conjugate. Cancer Res. 52, 4190-4195
22. Phanstiel, O.I., Price, H.L., Wang, L., Juusola, J., Kline, M. and Shah, S.M. (2000) The effect of polyamine homologation on the transport and cytotoxicity properties of polyamine-(DNAintercalator) conjugates. J. Org. Chem. 65, 5590-5599
23. Delcros, J.G., Tomasi, S., Duhieu, S., Foucault, M., Martin, B., Le Roch, M., Eifler-Lima, V., Renault, J. and Uriac, P. (2006) Effect of polyamine homologation on the transport and biological properties of heterocyclic amidines. J. Med. Chem. 49, 232-245
24. Bolden, J.E., Peart, M.J. and Johnstone, R.W. (2006) Anticancer activities of histone deacetylase inhibitors. Nat. Rev. Drug Discov. 5, 769-784
25. Varghese, S., Gupta, D., Baran, T., Jiemjit, A., Gore, S.D., Casero, Jr, R.A. and Woster, P.M. (2005) Alkyl-substituted polyaminohydroxamic acids: a novel class of targeted histone deacetylase inhibitors. J. Med. Chem. 48, 6350-6365
26. Varghese, S., Senanayake, T., Murray-Stewart, T., Doering, K., Fraser, A., Casero, Jr, R.A. and Woster, P.M. (2008) Polyaminohydroxamic acids and polyaminobenzamides as isoform selective histone deacetylase inhibitors. J. Med. Chem. 51, 2447-2456
27. Lee, M., Wynder, C., Schmidt, D., McCafferty, D. and Shiekhattar, R. (2006) Histone H3 lysine 4 demethylation is a target of nonselective antidepressive medications. Chem. Biol. 13, 563-567
28. Binda, C., Mattevi, A. and Edmondson, D.E. (2002) Structure-function relationships in flavoenzyme-dependent amine oxidations: a comparison of polyamine oxidase and monoamine oxidase. J. Biol. Chem. 277, 23973-23976
29. Wang, J., Hevi, S., Kurash, J.K., Lei, H., Gay, F., Bajko, J., Su, H., Sun, W., Chang, H., Xu, G. et al. (2009) The lysine demethylase LSD1 (KDM1) is required for maintenance of global DNA methylation. Nat. Genet. 41, 125-129
30. Baylin, S.B. and Ohm, J.E. (2006) Epigenetic gene silencing in cancer: a mechanism for early oncogenic pathway addiction? Nat. Rev. Cancer 6, 107-116
31. Kahl, P., Gullotti, L., Heukamp, L.C., Wolf, S., Friedrichs, N., Vorreuther, R., Solleder, G., Bastian, P.J., Ellinger, J., Metzger, E. et al. (2006) Androgen receptor coactivators lysine-specific histone demethylase 1 and four and a half LIM domain protein 2 predict risk of prostate cancer recurrence. Cancer Res. 66, 11341-11347
32. Scoumanne, A. and Chen, X. (2007) The lysine-specific demethylase 1 is required for cell proliferation in both p53-dependent and -independent manners. J. Biol. Chem. 282, 15471-15475
33. Bradley, C., van der Meer, R., Roodi, N., Yan, H., Chandrasekharan, M.B., Sun, Z.W., Mernaugh, R.L. and Parl, F.F. (2007) Carcinogen-induced histone alteration in normal human mammary epithelial cells. Carcinogenesis 28, 2184-2192
34. Schulte, J.H., Lim, S., Schramm, A., Friedrichs, N., Koster, J., Versteeg, R., Ora, I., Pajtler, K., Klein-Hitpass, L., Kuhfittig-Kulle, S. et al. (2009) Lysine-specific demethylase 1 is strongly expressed in poorly differentiated neuroblastoma: implications for therapy. Cancer Res. 69, 2065-2071
35. Wang, Y., Hacker, A., Murray-Stewart, T., Frydman, B., Valasinas, A., Fraser, A.V., Woster, P.M. and Casero, Jr, R.A. (2005) Properties of recombinant human N1-acetylpolyamine oxidase (hPAO): potential role in determining drug sensitivity. Cancer Chemother. Pharmacol. 56, 83-90
36. Huang, Y., Greene, E., Murray-Stewart, T., Goodwin, A., Baylin, S., Woster, P. and Casero, Jr, R. (2007) Inhibition of lysine-specific demethylase 1 by polyamine analogues results in reexpression of aberrantly silenced genes. Proc. Natl. Acad. Sci. U.S.A. 104, 8023-8028
37. Stavropoulos, P. and Hoelz, A. (2007) Lysine-specific demethylase 1 as a potential therapeutic target. Expert Opin. Ther. Targets 11, 809-820
38. Huang, Y., Murray Stewart, T., Wu, Y., Marton, L., Woster, P. and Casero, R. (2009) Novel oligoamine/polyamine analogues inhibit lysine-specific demethylase 1 (LSD1), induce re-expression of epigenetically silenced genes, and inhibit the growth of established human tumors in vivo. AACR 100th Annual Meeting, Denver, CO, U.S.A., 18-22 April 2009, Abstract LB-173
39. Murray-Stewart, T., Huang, Y., Woster, P. and Casero, R. (2008) Polyamine analogue inhibition of lysine-specific demethylase 1 in human acute myeloid leukemia cell lines. Proc. Am. Assoc. Cancer Res. 49, 2605
40. McGarvey, K., Fahrner, J., Greene, E., Martens, J., Jenuwein, T. and Baylin, S. (2006) Silenced tumor suppressor genes reactivated by DNA demethylation do not return to a fully euchromatic chromatin state. Cancer Res. 66, 3541-3549
41. Pruitt, K., Zinn, R.L., Ohm, J.E., McGarvey, K.M., Kang, S.H., Watkins, D.N., Herman, J.G. and Baylin, S.B. (2006) Inhibition of SIRT1 reactivates silenced cancer genes without loss of promoter DNA hypermethylation. PLoS Genet. 2, e40
42. Cameron, E., Bachman, K., Myohanen, S., Herman, J. and Baylin, S. (1999) Synergy of demethylation and histone deacetylase inhibition in the re-expression of genes silenced in cancer. Nat. Genet. 21, 103-107
43. Gore, S.D., Baylin, S., Sugar, E., Carraway, H., Miller, C.B., Carducci, M., Grever, M., Galm, O., Dauses, T., Karp, J.E. et al. (2006) Combined DNA methyltransferase and histone deacetylase inhibition in the treatment of myeloid neoplasms. Cancer Res. 66, 6361-6369