The promise and failures of epigenetic therapies for cancer treatment

Cancer Treatment Reviews

Volumn 40, Issue 1, 2014, Pages 153-169

  Bojang, Pasano ^a   Ramos, Kenneth S ^a  

^a UNIVERSITY OF LOUISVILLE   (United States)

Author keywords

DNA methyltransferases (DNMTs); Epigenetic; Epigenome; Histone acetyltransferases (HATs); Histone deacetylases (HDACs); Histone demetylases (HDMs); Histone methyltransferases (HMTs)

Indexed keywords

2 CYCLOHEXYL N (1 ISOPROPYL 4 PIPERIDINYL) 6 METHOXY 7 [3 (1 PYRROLIDINYL)PROPOXY] 4 QUINAZOLINAMINE; 4 PHENYLBUTYRIC ACID; 5 AZA 2' DEOXYCYTIDINE; ANTINEOPLASTIC AGENT; ARYLBUTYRIC ACID DERIVATIVE; AZACITIDINE; CYTARABINE; DACINOSTAT; DNA METHYLTRANSFERASE INHIBITOR; FLUCYTOSINE DEOXYRIBOSIDE; HISTONE ACETYLTRANSFERASE INHIBITOR; HISTONE DEACETYLASE INHIBITOR; HISTONE DEMETHYLASE INHIBITOR; HISTONE METHYLTRANSFERASE INHIBITOR; HYDRALAZINE; IMATINIB; LENALIDOMIDE; N (1 BENZYL 4 PIPERIDINYL) 2 (HEXAHYDRO 4 METHYL 1H 1,4 DIAZEPIN 1 YL) 6,7 DIMETHOXY 4 QUINAZOLINAMINE; N PHTHALOYLTRYPTOPHAN; PANOBINOSTAT; PROCAINE; RETINOIC ACID; ROMIDEPSIN; SINEFUNGIN; TACEDINALINE; TRANYLCYPROMINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VALPROIC ACID; VORINOSTAT; ZEBULARINE;

ACUTE GRANULOCYTIC LEUKEMIA; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; BLADDER CANCER; CANCER GENE THERAPY; CANCER GROWTH; CANCER INHIBITION; CANCER REGRESSION; COLORECTAL CANCER; CUTANEOUS T CELL LYMPHOMA; DRUG APPROVAL; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENTIATION; DRUG SENSITIVITY; DRUG SPECIFICITY; DRUG TARGETING; EPIGENETICS; ESOPHAGUS CANCER; GENE TARGETING; HUMAN; IC 50; LOW DRUG DOSE; LUNG NON SMALL CELL CANCER; MYELODYSPLASTIC SYNDROME; NONHUMAN; PHASE 1 CLINICAL TRIAL (TOPIC); PHASE 2 CLINICAL TRIAL (TOPIC); PHASE 3 CLINICAL TRIAL (TOPIC); REVIEW; SEQUENCE HOMOLOGY; TREATMENT FAILURE;

DNA METHYLTRANSFERASES (DNMTS); EPIGENETIC; EPIGENOME; HISTONE ACETYLTRANSFERASES (HATS); HISTONE DEACETYLASES (HDACS); HISTONE DEMETYLASES (HDMS); HISTONE METHYLTRANSFERASES (HMTS);

ANIMALS; DNA METHYLATION; EPIGENESIS, GENETIC; GENE EXPRESSION REGULATION, NEOPLASTIC; HISTONE DEACETYLASE INHIBITORS; HISTONES; HUMANS; MOLECULAR TARGETED THERAPY; NEOPLASMS; PROTEIN PROCESSING, POST-TRANSLATIONAL;

EID: 84887057701     PISSN: 03057372     EISSN: 15321967     Source Type: Journal    
DOI: 10.1016/j.ctrv.2013.05.009     Document Type: Review

References (215)

1. Waddington C.H. Selection of the genetic basis for an acquired character. Nature 1952, 169:625-626.
2. Berger S.L., Kouzarides T., Shiekhattar R., Shilatifard A. An operational definition of epigenetics. Genes Dev 2009, 23:781-783.
3. Fraga M.F., Ballestar E., Paz M.F., Ropero S., Setien F., Ballestar M.L., et al. Epigenetic differences arise during the lifetime of monozygotic twins. Proc Natl Acad Sci USA 2005, 102:10604-10609.
4. Esteller M. Epigenetics in cancer. N Engl J Med 2008, 358:1148-1159.
5. Dawson M.A., Kouzarides T. Cancer epigenetics: from mechanism to therapy Cell 2012, 150:12-27.
6. Santos-Rosa H., Schneider R., Bannister A.J., Sherriff J., Bernstein B.E., Emre N.C., et al. Active genes are tri-methylated at K4 of histone H3. Nature 2002, 419:407-411.
7. Heintzman N.D., Stuart R.K., Hon G., Fu Y., Ching C.W., Hawkins R.D., et al. Distinct and predictive chromatin signatures of transcriptional promoters and enhancers in the human genome. Nat Genet 2007, 39:311-318.
8. Ooi S.K., Qiu C., Bernstein E., Li K., Jia D., Yang Z., et al. DNMT3L connects unmethylated lysine 4 of histone H3 to de novo methylation of DNA. Nature 2007, 448:714-717.
9. Rosenfeld J.A., Wang Z., Schones D.E., Zhao K., DeSalle R., Zhang M.Q. Determination of enriched histone modifications in non-genic portions of the human genome. BMC Genomics 2009, 10:143.
10. Jacobs S.A., Taverna S.D., Zhang Y., Briggs S.D., Li J., Eissenberg J.C., et al. Specificity of the HP1 chromo domain for the methylated N-terminus of histone H3. EMBO J 2001, 20:5232-5241.
11. Cao R., Wang L., Wang H., Xia L., Erdjument-Bromage H., Tempst P., et al. Role of histone H3 lysine 27 methylation in Polycomb-group silencing. Science 2002, 298:1039-1043.
12. Barski A., Cuddapah S., Cui K., Roh T.Y., Schones D.E., Wang Z., et al. High-resolution profiling of histone methylations in the human genome. Cell 2007, 129:823-837.
13. Esteller M. Epigenetic gene silencing in cancer: the DNA hypermethylome. Hum Mol Genet 2007, 16(Spec No. 1):R50-R59.
14. Lee E., Iskow R., Yang L., Gokcumen O., Haseley P., Luquette L.J., et al. Landscape of somatic retrotransposition in human cancers. Science 2012, 337:967-971.
15. Bird A.W., Yu D.Y., Pray-Grant M.G., Qiu Q., Harmon K.E., Megee P.C., et al. Acetylation of histone H4 by Esa1 is required for DNA double-strand break repair. Nature 2002, 419:411-415.
16. Wang Y., Leung F.C. An evaluation of new criteria for CpG islands in the human genome as gene markers. Bioinformatics 2004, 20:1170-1177.
17. Doi A., Park I.H., Wen B., Murakami P., Aryee M.J., Irizarry R., et al. Differential methylation of tissue- and cancer-specific CpG island shores distinguishes human induced pluripotent stem cells embryonic stem cells and fibroblasts. Nat Genet 2009, 41:1350-1353.
18. Eden A., Gaudet F., Waghmare A., Jaenisch R. Chromosomal instability and tumors promoted by DNA hypomethylation. Science 2003, 300:455.
19. Howard G., Eiges R., Gaudet F., Jaenisch R., Eden A. Activation and transposition of endogenous retroviral elements in hypomethylation induced tumors in mice. Oncogene 2008, 27:404-408.
20. Chi P., Allis C.D., Wang G.G. Covalent histone modifications - miswritten, misinterpreted and mis-erased in human cancers. Nat Rev Cancer 2010, 10:457-469.
21. Allfrey V.G., Faulkner R., Mirsky A.E. Acetylation and methylation of histones and their possible role in the regulation of RNA Synthesis. Proc Natl Acad Sci USA 1964, 51:786-794.
22. Kleff S., Andrulis E.D., Anderson C.W., Sternglanz R. Identification of a gene encoding a yeast histone H4 acetyltransferase. J Biol Chem 1994, 270:24674-24677.
23. Allis C.D., Berger S.L., Cote J., Dent S., Jenuwien T., Kouzarides T., et al. New nomenclature for chromatin-modifying enzymes. Cell 2007, 131:633-636.
24. Allis C.D., Chicoine L.G., Richman R., Schulman I.G. Deposition-related histone acetylation in micronuclei of conjugating Tetrahymena. Proc Natl Acad Sci USA 1985, 82:8048-8052.
25. Ruiz-Carrillo A., Wangh L.J., Allfrey V.G. Processing of newly synthesized histone molecules. Science 1974, 190:117-128.
26. Parthun M.R., Widom J., Gottschling D.E. The major cytoplasmic histone acetyltransferase in yeast: links to chromatin replication and histone metabolism. Cell 1996, 87:85-94.
27. Yuan H., Marmorstein R. Histone acetyltransferases: rising ancient counterparts to protein kinases. Biopolymers 2012, 99(2):98-111.
28. Tanner K.G., Trievel R.C., Kuo M.H., Howard R.M., Berger S.L., Allis C.D., et al. Catalytic mechanism and function of invariant glutamic acid 173 from the histone acetyltransferase GCN5 transcriptional coactivator. J Biol Chem 1999, 274:18157-18160.
29. Tanner K.G., Langer M.R., Kim Y., Denu J.M. Kinetic mechanism of the histone acetyltransferase GCN5 from yeast. J Biol Chem 2000, 275:22048-22055.
30. Tanner K.G., Langer M.R., Denu J.M. Kinetic mechanism of human histone acetyltransferase P/CAF. Biochemistry 2000, 39:11961-11969.
31. Yan Y., Harper S., Speicher D.W., Marmorstein R. The catalytic mechanism of the ESA1 histone acetyltransferase involves a self-acetylated intermediate. Nat Struct Biol 2002, 9:862-869.
32. Boudreault A.A., Cronier D., Selleck W., Lacoste N., Utley R.T., Allard S., et al. Yeast enhancer of polycomb defines global Esa1-dependent acetylation of chromatin. Genes Dev 2003, 17:1415-1428.
33. Berndsen C.E., Albaugh B.N., Tan S., Denu J.M. Catalytic mechanism of a MYST family histone acetyltransferase. Biochemistry 2007, 46:623-629.
34. Liu X., Wang L., Zhao K., Thompson P.R., Hwang Y., Marmorstein R., et al. The structural basis of protein acetylation by the p300/CBP transcriptional coactivator. Nature 2008, 451:846-850.
35. Thompson P.R., Kurooka H., Nakatani Y., Cole P.A. Transcriptional coactivator protein p300. Kinetic characterization of its histone acetyltransferase activity. J Biol Chem 2001, 276:33721-33729.
36. Cullis P.M., Wolfenden R., Cousens L.S., Alberts B. M. Inhibition of histone acetylation by N-2-(S-coenzyme A)acetylspermidine amide, a multisubstrate analog. J Biol Chem 1982, 257:12165-12169.
37. Lau O.D., Courtney A.D., Vassilev A., Marzilli L.A., Cotter R.J., Nakatani Y., et al. p300/CBP-associated factor histone acetyltransferase processing of a peptide substrate. Kinetic analysis of the catalytic mechanism. J Biol Chem 2000, 275:21953-21959.
38. Sagar V., Zheng W., Thompson P.R., Cole P.A. Bisubstrate analogue structure-activity relationships for p300 histone acetyltransferase inhibitors. Bioorg Med Chem 2004, 12:3383-3390.
39. Balasubramanyam K., Altaf M., Varier R.A., Swaminathan V., Ravindran A., Sadhale P., et al. Polyisoprenylated benzophenone, garcinol, a natural histone acetyltransferase inhibitor, represses chromatin transcription and alters global gene expression. J Biol Chem 2004, 279:33716-33726.
40. Mantelingu K., Reddy B.A., Swaminathan V., Kishore A.H., Siddappa N.B., Kumar G.V., et al. Specific inhibition of p300-HAT alters global gene expression and represses HIV replication. Chem Biol 2007, 14:645-657.
41. Stimson L., Rowlands M.G., Newbatt Y.M., Smith N.F., Raynaud F.I., Rogers P., et al. Isothiazolones as inhibitors of PCAF and p300 histone acetyltransferase activity. Mol Cancer Ther 2005, 4:1521-1532.
42. Biel M., Kretsovali A., Karatzali E., Papamatheakis J., Giannis A. Design, synthesis, and biological evaluation of a small-molecule inhibitor of the histone acetyltransferase Gcn5. Angew Chem 2004, 43:3974-3976.
43. Murr R., Vaissiere T., Sawan C., Shukla V., Herceg Z. Orchestration of chromatin-based processes: mind the TRRAP. Oncogene 2007, 26:5358-5372.
44. Nagy Z., Tora L. Distinct GCN5/PCAF-containing complexes function as co-activators and are involved in transcription factor and global histone acetylation. Oncogene 2007, 26:5341-5357.
45. Sun Y., Jiang X., Chen S., Fernandes N., Price B.D. A role for the Tip60 histone acetyltransferase in the acetylation and activation of ATM. Proc Natl Acad Sci USA 2005, 102:13182-13187.
46. Sun Y., Xu Y., Roy K., Price B.D. DNA damage-induced acetylation of lysine 3016 of ATM activates ATM kinase activity. Mol Cell Biol 2007, 27:8502-8509.
47. Miller T.A., Witter D.J., Belvedere S. Histone deacetylase inhibitors. J Med Chem. 2003, 46:5097-5116.
48. Schemies J., Sippl W., Jung M. Histone deacetylase inhibitors that target tubulin. Cancer Lett 2009, 280:222-232.
49. North B.J., Verdin E. Sirtuins: Sir2-related NAD-dependent protein deacetylases. Genome Biol 2004, 5:224.
50. Westphal C.H., Dipp M.A., Guarente L. A therapeutic role for sirtuins in diseases of aging?. Trends Biochem Sci 2007, 32:555-560.
51. Fatkins D.G., Zheng W. Substituting N(epsilon)-thioacetyl-lysine for N(epsilon)-acetyl-lysine in peptide substrates as a general approach to inhibiting human NAD(+)-dependent protein deacetylases. Int J Mol Sci 2008, 9:1-11.
52. Solomon J.M., Pasupuleti R., Xu L., McDonagh T., Curtis R., DiStefano P.S., et al. Inhibition of SIRT1 catalytic activity increases p53 acetylation but does not alter cell survival following DNA damage. Mol Cell Biol 2006, 26:28-38.
53. Gui C.Y., Ngo L., Xu W.S., Richon V.M., Marks P.A. Histone deacetylase (HDAC) inhibitor activation of p21WAF1 involves changes in promoter-associated proteins, including HDAC1. Proc Natl Acad Sci USA 2004, 101:1241-1246.
54. Medda F., Russell R.J., Higgins M., McCarthy A.R., Campbell J., Slawin A.M., et al. Novel cambinol analogs as sirtuin inhibitors: synthesis, biological evaluation, and rationalization of activity. J Med Chem 2009, 52:2673-2682.
55. Sandor V., Senderowicz A., Mertins S., Sackett D., Sausville E., Blagosklonny M.V., et al. P21-dependent g(1)arrest with downregulation of cyclin D1 and upregulation of cyclin E by the histone deacetylase inhibitor FR901228. Br J Cancer 2000, 83:817-825.
56. Wharton W., Savell J., Cress W.D., Seto E., Pledger W.J. Inhibition of mitogenesis in Balb/c-3T3 cells by Trichostatin A. Multiple alterations in the induction and activation of cyclin-cyclin-dependent kinase complexes. J Biol Chem 2000, 275:33981-33987.
57. Bolden J.E., Peart M.J., Johnstone R.W. Anticancer activities of histone deacetylase inhibitors. Nat Rev Drug Discov 2006, 5:769-784.
58. Espino P.S., Drobic B., Dunn K.L., Davie J.R. Histone modifications as a platform for cancer therapy. J Cell Biochem 2005, 94:1088-1102.
59. Kelly W.K., Richon V.M., O'Connor O., Curley T., MacGregor-Curtelli B., Tong W., et al. Phase I clinical trial of histone deacetylase inhibitor: suberoylanilide hydroxamic acid administered intravenously. Clin Cancer Res 2003, 9:3578-3588.
60. Bhalla K.N. Epigenetic and chromatin modifiers as targeted therapy of hematologic malignancies. J Clin Oncol 2005, 23:3971-3993.
61. Dokmanovic M., Marks P.A. Prospects: histone deacetylase inhibitors. J Cell Biochem 2005, 96:293-304.
62. Marchion D.C., Bicaku E., Daud A.I., Richon V., Sullivan D.M., Munster P.N. Sequence-specific potentiation of topoisomerase II inhibitors by the histone deacetylase inhibitor suberoylanilide hydroxamic acid. J Cell Biochem 2004, 92:223-237.
63. Gore S.D., Baylin S., Sugar E., Carraway H., Miller C.B., Carducci M., et al. Combined DNA methyltransferase and histone deacetylase inhibition in the treatment of myeloid neoplasms. Cancer Res 2006, 66:6361-6369.
64. Maslak P., Chanel S., Camacho L.H., Soignet S., Pandolfi P.P., Guernah I., et al. Pilot study of combination transcriptional modulation therapy with sodium phenylbutyrate and 5-azacytidine in patients with acute myeloid leukemia or myelodysplastic syndrome. Leukemia 2006, 20:212-217.
65. Garcia-Manero G., Kantarjian H.M., Sanchez-Gonzalez B., Yang H., Rosner G., Verstovsek S., et al. Phase 1/2 study of the combination of 5-aza-2'-deoxycytidine with valproic acid in patients with leukemia. Blood 2006, 108:3271-3279.
66. Nemunaitis J.J., Orr D., Eager R., Cunningham C.C., Williams A., Mennel R., et al. Phase I study of oral CI-994 in combination with gemcitabine in treatment of patients with advanced cancer. Cancer J 2003, 9:58-66.
67. Undevia S.D., Kindler H.L., Janisch L., Olson S.C., Schilsky R.L., Vogelzang N.J., et al. A phase I study of the oral combination of CI-994, a putative histone deacetylase inhibitor, and capecitabine. Ann Oncol 2004, 15:1705-1711.
68. Pauer L.R., Olivares J., Cunningham C., Williams A., Grove W., Kraker A., et al. Phase I study of oral CI-994 in combination with carboplatin and paclitaxel in the treatment of patients with advanced solid tumors. Cancer Invest 2004, 22:886-896.
69. Kuendgen A., Strupp C., Aivado M., Bernhardt A., Hildebrandt B., Haas R., et al. Treatment of myelodysplastic syndromes with valproic acid alone or in combination with all-trans retinoic acid. Blood 2004, 104:1266-1269.
70. Pilatrino C., Cilloni D., Messa E., Morotti A., Giugliano E., Pautasso M., et al. Increase in platelet count in older, poor-risk patients with acute myeloid leukemia or myelodysplastic syndrome treated with valproic acid and all-trans retinoic acid. Cancer 2005, 104:101-109.
71. Raffoux E., Chaibi P., Dombret H., Degos L. Valproic acid and all-trans retinoic acid for the treatment of elderly patients with acute myeloid leukemia. Haematologica 2005, 90:986-988.
72. Nimmanapalli R., Fuino L., Stobaugh C., Richon V., Bhalla K. Cotreatment with the histone deacetylase inhibitor suberoylanilide hydroxamic acid (SAHA) enhances imatinib-induced apoptosis of Bcr-Abl-positive human acute leukemia cells. Blood 2003, 101:3236-3239.
73. Wittmann S., Bali P., Donapaty S., Nimmanapalli R., Guo F., Yamaguchi H., et al. Flavopiridol down-regulates antiapoptotic proteins and sensitizes human breast cancer cells to epothilone B-induced apoptosis. Cancer Res 2003, 63:93-99.
74. Yu C., Rahmani M., Conrad D., Subler M., Dent P., Grant S. The proteasome inhibitor bortezomib interacts synergistically with histone deacetylase inhibitors to induce apoptosis in Bcr/Abl+ cells sensitive and resistant to STI571. Blood 2003, 102:3765-3774.
75. Fiskus W., Pranpat M., Bali P., Balasis M., Kumaraswamy S., Boyapalle S., et al. Combined effects of novel tyrosine kinase inhibitor AMN107 and histone deacetylase inhibitor LBH589 against Bcr-Abl-expressing human leukemia cells. Blood 2006, 108:645-652.
76. Bourc'his D., Xu G.L., Lin C.S., Bollman B., Bestor T.H. Dnmt3L and the establishment of maternal genomic imprints. Science 2001, 294:2536-2539.
77. Chen Z.X., Mann J.R., Hsieh C.L., Riggs A.D., Chedin F. Physical and functional interactions between the human DNMT3L protein and members of the de novo methyltransferase family. J Cell Biochem 2005, 95:902-917.
78. Dhayalan A., Rajavelu A., Rathert P., Tamas R., Jurkowska R.Z., Ragozin S., et al. The Dnmt3a PWWP domain reads histone 3 lysine 36 trimethylation and guides DNA methylation. J Biol Chem 2010, 285:26114-26120.
79. Okano M., Xie S., Li E. Dnmt2 is not required for de novo and maintenance methylation of viral DNA in embryonic stem cells. Nucleic Acids Res 1998, 26:2536-2540.
80. Goll M.G., Kirpekar F., Maggert K.A., Yoder J.A., Hsieh C.L., Zhang X., et al. Methylation of tRNAAsp by the DNA methyltransferase homolog Dnmt2. Science 2006, 311:395-398.
81. Robertson K.D., Uzvolgyi E., Liang G., Talmadge C., Sumegi J., Gonzales F.A., et al. The human DNA methyltransferases (DNMTs) 1, 3a and 3b: coordinate mRNA expression in normal tissues and overexpression in tumors. Nucleic Acids Res 1999, 27:2291-2298.
82. Fuks F., Hurd P.J., Deplus R., Kouzarides T. The DNA methyltransferases associate with HP1 and the SUV39H1 histone methyltransferase. Nucleic Acids Res 2003, 31:2305-2312.
83. Fuks F., Burgers W.A., Brehm A., Hughes-Davies L., Kouzarides T. DNA methyltransferase Dnmt1 associates with histone deacetylase activity. Nat Genet 2000, 24:88-91.
84. Geiman T.M., Sankpal U.T., Robertson A.K., Zhao Y., Robertson K.D. DNMT3B interacts with hSNF2H chromatin remodeling enzyme, HDACs 1 and 2, and components of the histone methylation system. Biochem Biophys Res Commun 2004, 318:544-555.
85. Okano M., Bell D.W., Haber D.A., Li E. DNA methyltransferases Dnmt3a and Dnmt3b are essential for de novo methylation and mammalian development. Cell 1999, 99:247-257.
86. Klose R.J., Bird A.P. Genomic DNA methylation: the mark and its mediators. Trends Biochem Sci 2006, 31:89-97.
87. Kriaucionis S., Heintz N. The nuclear DNA base 5-hydroxymethylcytosine is present in Purkinje neurons and the brain. Science 2009, 324:929-930.
88. Tahiliani M., Koh K.P., Shen Y., Pastor W.A., Bandukwala H., Brudno Y., et al. Conversion of 5-methylcytosine to 5-hydroxymethylcytosine in mammalian DNA by MLL partner TET1. Science 2009, 324:930-935.
89. Baylin S.B., Jones P.A. A decade of exploring the cancer epigenome - biological and translational implications. Nat Rev Cancer 2011, 11:726-734.
90. Rius M., Stresemann C., Keller D., Brom M., Schirrmacher E., Keppler D., et al. Human concentrative nucleoside transporter 1-mediated uptake of 5-azacytidine enhances DNA demethylation. Mol Cancer Ther 2009, 8:225-231.
91. Huber-Ruano I., Pastor-Anglada M. Transport of nucleoside analogs across the plasma membrane: a clue to understanding drug-induced cytotoxicity. Curr Drug Metab 2009, 10:347-358.
92. Stresemann C., Lyko F. Modes of action of the DNA methyltransferase inhibitors azacytidine and decitabine. Int J Cancer 2008, 123:8-13.
93. Issa J.P., Kantarjian H.M. Targeting DNA methylation. Clin Cancer Res 2009, 15:3938-3946.
94. Momparler R.L., Rossi M., Bouchard J., Vaccaro C., Momparler L.F., Bartolucci S. Kinetic interaction of 5-AZA-2'-deoxycytidine-5'-monophosphate and its 5'-triphosphate with deoxycytidylate deaminase. Mol Pharmacol 1984, 25:436-440.
95. Ghoshal K., Datta J., Majumder S., Bai S., Kutay H., Motiwala T., et al. 5-Aza-deoxycytidine induces selective degradation of DNA methyltransferase 1 by a proteasomal pathway that requires the KEN box, bromo-adjacent homology domain, and nuclear localization signal. Mol Cell Biol 2005, 25:4727-4741.
96. Kuo H.K., Griffith J.D., Kreuzer K.N. 5-Azacytidine induced methyltransferase-DNA adducts block DNA replication in vivo. Cancer Res 2007, 67:8248-8254.
97. Soriano A.O., Yang H., Faderl S., Estrov Z., Giles F., Ravandi F., et al. Safety and clinical activity of the combination of 5-azacytidine, valproic acid, and all-trans retinoic acid in acute myeloid leukemia and myelodysplastic syndrome. Blood 2007, 110:2302-2308.
98. Voso M.T., Santini V., Finelli C., Musto P., Pogliani E., Angelucci E., et al. Valproic acid at therapeutic plasma levels may increase 5-azacytidine efficacy in higher risk myelodysplastic syndromes. Cancer Res 2009, 15:5002-5007.
99. Sekeres M.A., List A.F., Cuthbertson D., Paquette R., Ganetzky R., Latham D., et al. Phase I combination trial of lenalidomide and azacitidine in patients with higher-risk myelodysplastic syndromes. J Clin Oncol 2010, 28:2253-2258.
100. Zhou D.C., Kim S.H., Ding W., Schultz C., Warrell R.P., Gallagher R.E. Frequent mutations in the ligand-binding domain of PML-RARalpha after multiple relapses of acute promyelocytic leukemia: analysis for functional relationship to response to all-trans retinoic acid and histone deacetylase inhibitors in vitro and in vivo. Blood 2002, 99:1356-1363.
101. Cheng J.C., Matsen C.B., Gonzales F.A., Ye W., Greer S., Marquez V.E., et al. Inhibition of DNA methylation and reactivation of silenced genes by zebularine. J Natl Cancer Inst 2003, 95:399-409.
102. Flotho C., Claus R., Batz C., Schneider M., Sandrock I., Ihde S., et al. The DNA methyltransferase inhibitors azacitidine, decitabine and zebularine exert differential effects on cancer gene expression in acute myeloid leukemia cells. Leukemia 2009, 23:1019-1028.
103. Billam M., Sobolewski M.D., Davidson N.E. Effects of a novel DNA methyltransferase inhibitor zebularine on human breast cancer cells. Breast Cancer Res Treat 2010, 120:581-592.
104. Dote H., Cerna D., Burgan W.E., Camphausen K., Tofilon P.J. ErbB3 expression predicts tumor cell radiosensitization induced by Hsp90 inhibition. Cancer Res 2005, 65:6967-6975.
105. Balch C., Yan P., Craft T., Young S., Skalnik D.G., Huang T.H., et al. Antimitogenic and chemosensitizing effects of the methylation inhibitor zebularine in ovarian cancer. Mol Cancer Ther 2005, 4:1505-1514.
106. Hellebrekers D.M., Jair K.W., Vire E., Eguchi S., Hoebers N.T., Fraga M.F., et al. Angiostatic activity of DNA methyltransferase inhibitors. Mol Cancer Ther 2006, 51:457-475.
107. Zhou L., Cheng X., Connolly B.A., Dickman M.J., Hurd P.J., Hornby D.P. Zebularine: a novel DNA methylation inhibitor that forms a covalent complex with DNA methyltransferases. J Mol Biol 2002, 321:591-599.
108. Beumer J.H., Parise R.A., Newman E.M., Doroshow J.H., Synold T.W., Lenz H.J., et al. Concentrations of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine (FdCyd) and its cytotoxic metabolites in plasma of patients treated with FdCyd and tetrahydrouridine (THU). Cancer Chemother Pharmacol 2008, 62:363-368.
109. Jones P.A., Taylor S.M. Cellular differentiation, cytidine analogs and DNA methylation. Cell 1980, 20:85-93.
110. Reither S., Li F., Gowher H., Jeltsch A. Catalytic mechanism of DNA-(cytosine-C5)-methyltransferases revisited: covalent intermediate formation is not essential for methyl group transfer by the murine Dnmt3a enzyme. J Mol Biol 2003, 329:675-684.
111. Gowher H., Jeltsch A. Mechanism of inhibition of DNA methyltransferases by cytidine analogs in cancer therapy. Cancer Biol Ther 2004, 3:1062-1068.
112. Kratzke R.A., Wang X., Wong L., Kratzke M.G., Green M.R., Vokes E.E., et al. Response to the methylation inhibitor dihydro-5-azacytidine in mesothelioma is not associated with methylation of p16INK4a: results of cancer and leukemia group B 159904. J Thoracic Oncol 2008, 3:417-421.
113. Villar-Garea A., Fraga M.F., Espada J., Esteller M. Procaine is a DNA-demethylating agent with growth-inhibitory effects in human cancer cells. Cancer Res 2003, 63:4984-4989.
114. Singh N., Duenas-Gonzalez A., Lyko F., Medina-Franco J.L. Molecular modeling and molecular dynamics studies of hydralazine with human DNA methyltransferase 1. ChemMedChem 2009, 4:792-799.
115. Mund C., Brueckner B., Lyko F. Reactivation of epigenetically silenced genes by DNA methyltransferase inhibitors: basic concepts and clinical applications. Epigenetics 2006, 1:7-13.
116. Song Y., Zhang C. Hydralazine inhibits human cervical cancer cell growth in vitro in association with APC demethylation and re-expression. Cancer Chemother Pharmacol 2009, 63:605-613.
117. Lee B.H., Yegnasubramanian S., Lin X., Nelson W.G. Procainamide is a specific inhibitor of DNA methyltransferase 1. J Biol Chem 2005, 280:40749-40756.
118. Brueckner B., Garcia Boy R., Siedlecki P., Musch T., Kliem H.C., Zielenkiewicz P., et al. Epigenetic reactivation of tumor suppressor genes by a novel small-molecule inhibitor of human DNA methyltransferases. Cancer Res 2005, 65:6305-6311.
119. Suzuki T., Tanaka R., Hamada S., Nakagawa H., Miyata N. Design, synthesis, inhibitory activity, and binding mode study of novel DNA methyltransferase 1 inhibitors. Bioorg Med Chem Lett 2010, 20:1124-1127.
120. Savickiene J., Treigyte G., Jazdauskaite A., Borutinskaite V.V., Navakauskiene R. DNA methyltransferase inhibitor RG108 and histone deacetylase inhibitors cooperate to enhance NB4 cell differentiation and E-cadherin re-expression by chromatin remodeling. Cell Biol Int. 2012, 36:1067-1078.
121. Savickiene J., Treigyte G., Borutinskaite V.V., Navakauskiene R. Antileukemic activity of combined epigenetic agents, DNMT inhibitors zebularine and RG108 with HDAC inhibitors, against promyelocytic leukemia HL-60 cells. Cell Mol Biol Lett. 2012, 17:501-525.
122. Gershey E.L., Haslett G.W., Vidali G., Allfrey V.G. Chemical studies of histone methylation. Evidence for the occurrence of 3-methylhistidine in avian erythrocyte histone fractions. J Biol Chem 1969, 244:4871-4877.
123. Byvoet P., Shepherd G.R., Hardin J.M., Noland B.J. The distribution and turnover of labeled methyl groups in histone fractions of cultured mammalian cells. Arch Biochem Biophys 1969, 148:558-567.
124. Dillon S.C., Zhang X., Trievel R.C., Cheng X. The SET-domain protein superfamily: protein lysine methyltransferases. Genome Biol 2005, 6:227.
125. Qian C., Wang X., Manzur K., Sachchidanand M., Farooq A., Zeng L., et al. Structural insights of the specificity and catalysis of a viral histone H3 lysine 27 methyltransferase. J Mol Biol 2006, 359:86-96.
126. Xiao B., Wilson J.R., Gamblin S. JSET domains and histone methylation. Curr Opin Struct Biol 2003, 13:699-705.
127. Min J., Feng Q., Li Z., Zhang Y., Xu R.M. Structure of the catalytic domain of human DOT1L, a non-SET domain nucleosomal histone methyltransferase. Cell 2003, 112:711-723.
128. Wilson J.R., Jing C., Walker P.A., Martin S.R., Howell S.A., Blackburn G.M., et al. Crystal structure and functional analysis of the histone methyltransferase SET7/9. Cell 2002, 111:105-115.
129. Taylor W.R., Xiao B., Gamblin S.J., Lin K. A knot or not a knot? SETting the record 'straight' on proteins. Comput Biol Chem 2003, 27:11-15.
130. Xiao B., Jing C., Wilson J.R., Walker P.A., Vasisht N., Kelly G., et al. Structure and catalytic mechanism of the human histone methyltransferase SET7/9. Nature 2003, 421:652-656.
131. Zhang X., Tamaru H., Khan S.I., Horton J.R., Keefe L.J., Selker E.U., et al. Structure of the Neurospora SET domain protein DIM-5, a histone H3 lysine methyltransferase. Cell 2002, 111:117-127.
132. Xiao B., Jing C., Kelly G., Walker P.A., Muskett F.W., Frenkiel T.A., et al. Specificity and mechanism of the histone methyltransferase Pr-Set7. Genes Dev 2005, 19:1444-1454.
133. Hu P., Zhang Y. Catalytic mechanism and product specificity of the histone lysine methyltransferase SET7/9: an ab initio QM/MM-FE study with multiple initial structures. J Am Chem Soc 2006, 128:1272-1278.
134. Zhang X., Yang Z., Khan S.I., Horton J.R., Tamaru H., Selker E.U., et al. Structural basis for the product specificity of histone lysine methyltransferases. Mol Cell 2003, 12:177-185.
135. Qian C., Zhou M.M. SET domain protein lysine methyltransferases: Structure, specificity and catalysis. Cell Mol Life Sci 2006, 63:2755-2763.
136. Cheng X., Collins R.E., Zhang X. Structural and sequence motifs of protein (histone) methylation enzymes. Annu Rev Biophys Biomol Struct 2005, 34:267-294.
137. Kwon T., Chang J.H., Kwak E., Lee C.W., Joachimiak A., Kim Y.C., et al. Mechanism of histone lysine methyl transfer revealed by the structure of SET7/9-AdoMet. EMBO J 2003, 22:292-303.
138. Wu H., Moshkina N., Min J., Zeng H., Joshua J., Zhou M.M., et al. Structural basis for substrate specificity and catalysis of human histone acetyltransferase 1. PNAS 2012, 109:8925-8930.
139. Guo H.B., Guo H. Mechanism of histone methylation catalyzed by protein lysine methyltransferase SET7/9 and origin of product specificity. PNAS 2007, 104:8797-8802.
140. Collins R.E., Tachibana M., Tamaru H., Smith K.M., Jia D., Zhang X., et al. In vitro and in vivo analyses of a Phe/Tyr switch controlling product specificity of histone lysine methyltransferases. JBC 2005, 280:5563-5570.
141. Smith B.C., Denu J.M. Chemical mechanisms of histone lysine and arginine modifications. Biochim Biophys Acta 2009, 1789:45-57.
142. Wu H., Chen X., Xiong J., Li Y., Li H., Ding X., et al. Histone methyltransferase G9a contributes to H3K27 methylation in vivo. Cell Res 2011, 21:365-367.
143. Milne T.A., Briggs S.D., Brock H.W., Martin M.E., Gibbs D., Allis C.D., et al. MLL targets SET domain methyltransferase activity to Hox gene promoters. Mol Cell 2002, 10:1107-1117.
144. Milne T.A., Martin M.E., Brock H.W., Slany R.K., Hess J.L. Leukemogenic MLL fusion proteins bind across a broad region of the Hox a9 locus, promoting transcription and multiple histone modifications. Cancer Res 2005, 65:11367-11374.
145. Huang H., Zhang J., Shen W., Wang X., Wu J., Shi Y. Solution structure of the second bromodomain of Brd2 and its specific interaction with acetylated histone tails. BMC Struct Biol 2007, 7:57.
146. Bannister A.J., Zegerman P., Partridge J.F., Miska E.A., Thomas J.O., Allshire R.C., et al. Selective recognition of methylated lysine 9 on histone H3 by the HP1 chromo domain. Nature 2001, 410:120-124.
147. Lachner M., O'Carroll D., Rea S., Mechtler K., Jenuwein T. Methylation of histone H3 lysine 9 creates a binding site for HP1 proteins. Nature 2001, 410:116-120.
148. Valk-Lingbeek M.E., Bruggeman S.W., van Lohuizen M. Stem cells and cancer; the polycomb connection. Cell 2004, 118:409-418.
149. Fang J.Y., Lu Y.Y. Effects of histone acetylation and DNA methylation on p21(WAF1) regulation. World J Gastroenterol 2002, 8:400-405.
150. Dong C., Wu Y., Wang Y., Wang C., Kang T., Rychahou P.G., et al. Interaction with Suv39H1 is critical for Snail-mediated E-cadherin repression in breast cancer. Oncogene 2013, 32:1351-1362.
151. Sneeringer C.J., Scott M.P., Kuntz K.W., Knutson S.K., Pollock R.M., Richon V.M., et al. Coordinated activities of wild-type plus mutant EZH2 drive tumor-associated hypertrimethylation of lysine 27 on histone H3 (H3K27) in human B-cell lymphomas. PNAS 2010, 107:20980-20985.
152. Sanders D.S., Muntean A.G., Hess J.L. Significance of AF4-MLL reciprocal fusion in t(4;11) leukemias?. Leuk Res 2011, 35:299-300.
153. Liedtke M., Cleary M.L. Therapeutic targeting of MLL. Blood 2009, 113:6061-6068.
154. Vedel M., Robert-Gero M. Comparative effect of S-adenosyl-homocysteine (SAH) and Sinefungin on tRNA-base methylation in whole cells and in vitro. FEBS Lett 1981, 128:87-89.
155. Cheng D., Yadav N., King R.W., Swanson M.S., Weinstein E.J., Bedford M.T. Small molecule regulators of protein arginine methyltransferases. JBC 2004, 279:23892-23899.
156. Greiner D., Bonaldi T., Eskeland R., Roemer E., Imhof A. Identification of a specific inhibitor of the histone methyltransferase SU(VAR)3-9. Nat Chem Biol 2005, 1:143-145.
157. Vedel M., Lawrence F., Robert-Gero M., Lederer E. The antifungal antibiotic sinefungin as a very active inhibitor of methyltransferases and of the transformation of chick embryo fibroblasts by Rous sarcoma virus. Biochem Biophys Res Commun 1978, 85:371-376.
158. Iwasa E., Hamashima Y., Fujishiro S., Higuchi E., Ito A., Yoshida M., et al. Total synthesis of (+)-chaetocin and its analogues: their histone methyltransferase G9a inhibitory activity. J Am Chem Soc 2010, 132:4078-4079.
159. Chang Y., Zhang X., Horton J.R., Upadhyay A.K., Spannhoff A., Liu J., et al. Structural basis for G9a-like protein lysine methyltransferase inhibition by BIX-01294. Nat Struct Mol Biol 2009, 16:312-317.
160. Liu F., Chen X., Allali-Hassani A., Quinn A.M., Wasney G.A., Dong A., et al. Discovery of a 2,4-diamino-7-aminoalkoxyquinazoline as a potent and selective inhibitor of histone lysine methyltransferase G9a. J Med Chem 2009, 52:7950-7953.
161. Liu F., Chen X., Allali-Hassani A., Quinn A.M., Wigle T.J., Wasney G.A., et al. Protein lysine methyltransferase G9a inhibitors: design, synthesis, and structure activity relationships of 2,4-diamino-7-aminoalkoxy-quinazolines. J Med Chem 2010, 53:5844-5857.
162. Liu F., Barsyte-Lovejoy D., Allali-Hassani A., He Y., Herold J.M., Chen X., et al. Optimization of cellular activity of G9a inhibitors 7-aminoalkoxy-quinazolines. J Med Chem 2011, 54:6139-6150.
163. Vedadi M., Barsyte-Lovejoy D., Liu F., Rival-Gervier S., Allali-Hassani A., Labrie V., et al. A chemical probe selectively inhibits G9a and GLP methyltransferase activity in cells. Nat Chem Biol 2011, 7:566-574.
164. Trapp J., Meier R., Hongwiset D., Kassack M.U., Sippl W., Jung M. Structure-activity studies on suramin analogues as inhibitors of NAD+-dependent histone deacetylases (sirtuins). ChemMedChem 2007, 2:1419-1431.
165. Ragno R., Simeoni S., Castellano S., Vicidomini C., Mai A., Caroli A., et al. Small molecule inhibitors of histone arginine methyltransferases: homology modeling, molecular docking, binding mode analysis, and biological evaluations. J Med Chem 2007, 50:1241-1253.
166. Daigle S.R., Olhava E.J., Therkelsen C.A., Majer C.R., Sneeringer C.J., Song J., et al. Selective killing of mixed lineage leukemia cells by a potent small-molecule DOT1L inhibitor. Cancer Cell 2011, 20:53-65.
167. Tan M., Luo H., Lee S., Jin F., Yang J.S., Montellier E., et al. Identification of 67 histone marks and histone lysine crotonylation as a new type of histone modification. Cell 2011, 146:1016-1028.
168. Peters A.H., O'Carroll D., Scherthan H., Mechtler K., Sauer S., Schofer C., et al. Loss of the Suv39h histone methyltransferases impairs mammalian heterochromatin and genome stability. Cell 2001, 107:323-337.
169. Tachibana M., Sugimoto K., Nozaki M., Ueda J., Ohta T., Ohki M., et al. G9a histone methyltransferase plays a dominant role in euchromatic histone H3 lysine 9 methylation and is essential for early embryogenesis. Genes Dev 2002, 16:1779-1791.
170. Peters A.H., Kubicek S., Mechtler K., O'Sullivan R.J., Derijck A.A., Perez-Burgos L., et al. Partitioning and plasticity of repressive histone methylation states in mammalian chromatin. Mol Cell 2003, 12:1577-1589.
171. Sun L., Wang M., Lv Z., Yang N., Liu Y., Bao S., et al. Structural insights into protein arginine symmetric dimethylation by PRMT5. PNAS 2011, 108:20538-20543.
172. Ferguson A.D., Larsen N.A., Howard T., Pollard H., Green I., Grande C., et al. Structural basis of substrate methylation and inhibition of SMYD2. Structure 2011, 19:1262-1273.
173. Chuikov S., Kurash J.K., Wilson J.R., Xiao B., Justin N., Ivanov G.S., et al. Regulation of p53 activity through lysine methylation. Nature 2004, 432:353-360.
174. Huang J., Perez-Burgos L., Placek B.J., Sengupta R., Richter M., Dorsey J.A., et al. Repression of p53 activity by Smyd2-mediated methylation. Nature 2006, 444:629-632.
175. Saddic L.A., West L.E., Aslanian A., Yates J.R., Rubin S.M., Gozani O., et al. Methylation of the retinoblastoma tumor suppressor by SMYD2. J Biol Chem 2010, 285:37733-37740.
176. Huang J., Dorsey J., Chuikov S., Perez-Burgos L., Zhang X., Jenuwein T., et al. G9a and Glp methylate lysine 373 in the tumor suppressor p53. J Biol Chem 2010, 285:9636-9641.
177. Shi Y., Lan F., Matson C., Mulligan P., Whetstine J.R., Cole P.A., et al. Histone demethylation mediated by the nuclear amine oxidase homolog LSD1. Cell 2004, 119:941-953.
178. Tsukada Y., Fang J., Erdjument-Bromage H., Warren M.E., Borchers C.H., Tempst P., et al. Histone demethylation by a family of JmjC domain-containing proteins. Nature 2006, 439:811-816.
179. Wang Y., Wysocka J., Sayegh J., Lee Y.H., Perlin J.R., Leonelli L., et al. Human PAD4 regulates histone arginine methylation levels via demethylimination. Science 2004, 306:279-283.
180. Cuthbert G.L., Daujat S., Snowden A.W., Erdjument-Bromage H., Hagiwara T., Yamada M., et al. Histone deimination antagonizes arginine methylation. Cell 2004, 118:545-553.
181. Karytinos A., Forneris F., Profumo A., Ciossani G., Battaglioli E., Binda C., et al. A novel mammalian flavin-dependent histone demethylase. J Biol Chem 2009, 284:17775-17782.
182. Stavropoulos P., Blobel G., Hoelz A. Crystal structure and mechanism of human lysine-specific demethylase-1. Nat Struct Mol Biol 2006, 13:626-632.
183. Chen Y., Yang Y., Wang F., Wan K., Yamane K., Zhang Y., et al. Crystal structure of human histone lysine-specific demethylase 1 (LSD1). PNAS 2006, 103:13956-13961.
184. Metzger E., Wissmann M., Yin N., Muller J.M., Schneider R., Peters A.H., et al. LSD1 demethylates repressive histone marks to promote androgen-receptor-dependent transcription. Nature 2005, 437:436-439.
185. Lee M.G., Wynder C., Cooch N., Shiekhattar R. An essential role for CoREST in nucleosomal histone 3 lysine 4 demethylation. Nature 2005, 437:432-435.
186. Trewick S.C., McLaughlin P.J., Allshire R.C. Methylation: lost in hydroxylation?. EMBO Rep 2005, 6:315-320.
187. Hausinger R.P. FeII/alpha-ketoglutarate-dependent hydroxylases and related enzymes. Crit Rev Biochem Mol Biol 2004, 39:21-68.
188. Klose R.J., Kallin E.M., Zhang Y. JmjC-domain-containing proteins and histone demethylation. Nat Rev Genet 2006, 7:715-727.
189. Cloos P.A., Christensen J., Agger K., Maiolica A., Rappsilber J., Antal T., et al. The putative oncogene GASC1 demethylates tri- and dimethylated lysine 9 on histone H3. Nature 2006, 442:307-311.
190. Fodor B.D., Kubicek S., Yonezawa M., O'Sullivan R.J., Sengupta R., Perez-Burgos L., et al. Jmjd2b antagonizes H3K9 trimethylation at pericentric heterochromatin in mammalian cells. Genes Dev 2006, 20:1557-1562.
191. Kahl P., Gullotti L., Heukamp L.C., Wolf S., Friedrichs N., Vorreuther R., et al. 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 2006, 66:11341-11347.
192. Wissmann M., Yin N., Muller J.M., Greschik H., Fodor B.D., Jenuwein T., et al. Cooperative demethylation by JMJD2C and LSD1 promotes androgen receptor-dependent gene expression. Nat Cell Biol 2006, 9:347-353.
193. Wellmann S., Bettkober M., Zelmer A., Seeger K., Faigle M., Eltzschig H.K., et al. Hypoxia upregulates the histone demethylase JMJD1A via HIF-1. Biochem Biophys Res Commun 2008, 372:892-897.
194. Pollard P.J., Loenarz C., Mole D.R., McDonough M.A., Gleadle J.M., Schofield C.J., et al. Regulation of Jumonji-domain-containing histone demethylases by hypoxia-inducible factor (HIF)-1alpha. Biochem J 2008, 416:387-394.
195. Yang J., Ledaki I., Turley H., Gatter K.C., Montero J.C., Li J.L., et al. Role of hypoxia-inducible factors in epigenetic regulation via histone demethylases. Ann N Y Acad Sci 2009, 1177:185-197.
196. Sharma S.V., Lee D.Y., Li B., Quinlan M.P., Takahashi F., Maheswaran S., et al. A chromatin-mediated reversible drug-tolerant state in cancer cell subpopulations. Cell 2010, 141:69-80.
197. Burger A., Yost W.L. Arylcycloalkylamines, 1,2-Phenylcyclopropylamine. J Am Chem Soc 1948, 70(6):2198.
198. Tedeschi R.E., Tedeschi D.H., Ames P.L., Cook L., Mattis P.A., Fellows E.J. Some pharmacological observations on tranylcypromine (SKF trans-385) a potent inhibitor of monoamine oxidase. Proc Soc Exp Biol Med 1959, 102:380-381.
199. West E.D., Dally P.J. Effects of iproniazid in depressive syndromes. Br Med J 1959, 1:1491-1494.
200. Culhane J.C., Wang D., Yen P.M., Cole P.A. Comparative analysis of small molecules and histone substrate analogues as LSD1 lysine demethylase inhibitors. J Am Chem Soc 2010, 132:3164-3176.
201. Ueda R., Suzuki T., Mino K., Tsumoto H., Nakagawa H., Hasegawa M., et al. Identification of cell-active lysine specific demethylase 1-selective inhibitors. J Am Chem Soc 2009, 131:17536-17537.
202. Mimasu S., Umezawa N., Sato S., Higuchi T., Umehara T., Yokoyama S. Structurally designed trans-2-phenylcyclopropylamine derivatives potently inhibit histone demethylase LSD1/KDM1. Biochemistry 2010, 49:6494-6503.
203. Szewczuk L.M., Culhane J.C., Yang M., Majumdar A., Yu H., Cole P.A. Mechanistic analysis of a suicide inactivator of histone demethylase LSD1. Biochemistry 2007, 46:6892-6902.
204. Huang Y., Greene E., Stewart T.Murray, Goodwin A.C., Baylin S.B., Woster P.M., et al. Inhibition of lysine-specific demethylase 1 by polyamine analogues results in reexpression of aberrantly silenced genes. PNAS 2007, 104:8023-8028.
205. Bi X., Lopez C., Bacchi C.J., Rattendi D., Woster P.M. Novel alkylpolyaminoguanidines and alkylpolyaminobiguanides with potent antitrypanosomal activity. Bioorg Med Chem Lett 2006, 16:3229-3232.
206. Huang Y., Stewart T.M., Wu Y., Baylin S.B., Marton L.J., Perkins B., et al. Novel oligoamine analogues inhibit lysine-specific demethylase 1 and induce reexpression of epigenetically silenced genes. Clin Cancer Res 2009, 15:7217-7228.
207. Hirsila M., Koivunen P., Gunzler V., Kivirikko K.I., Myllyharju J. Characterization of the human prolyl 4-hydroxylases that modify the hypoxia-inducible factor. J Biol Chem 2003, 278:30772-30780.
208. Ivan M., Haberberger T., Gervasi D.C., Michelson K.S., Gunzler V., Kondo K., et al. Biochemical purification and pharmacological inhibition of a mammalian prolyl hydroxylase acting on hypoxia-inducible factor. PNAS 2002, 13459-13464.
209. McDonough M.A., McNeill L.A., Tilliet M., Papamicael C.A., Chen Q.Y., Banerji B., et al. Selective inhibition of factor inhibiting hypoxia-inducible factor. J Am Chem Soc 2005, 127:7680-7681.
210. Rose N.R., Ng S.S., Mecinovic J., Lienard B.M., Bello S.H., Sun Z., et al. Inhibitor scaffolds for 2-oxoglutarate-dependent histone lysine demethylases. J Med Chem 2008, 51:7053-7056.
211. Rose N.R., Woon E.C., Kingham G.L., King O.N., Mecinovic J., Clifton I.J., et al. Selective inhibitors of the JMJD2 histone demethylases: combined nondenaturing mass spectrometric screening and crystallographic approaches. J Med Chem 2010, 53:1810-1818.
212. Tiainen P., Pasanen A., Sormunen R., Myllyharju J. Characterization of recombinant human prolyl 3-hydroxylase isoenzyme 2, an enzyme modifying the basement membrane collagen IV. J Biol Chem 2008, 283:19432-19439.
213. Belvedere S., Witter D.J., Yan J., Secrist J.P., Richon V., Miller T.A. Aminosuberoyl hydroxamic acids (ASHAs): a potent new class of HDAC inhibitors. Bioorg Med Chem Lett 2007, 17:3969-3971.
214. King O.N., Li X.S., Sakurai M., Kawamura A., Rose N.R., Ng S.S., et al. Quantitative high-throughput screening identifies 8-hydroxyquinolines as cell-active histone demethylase inhibitors. PLoS One 2010, 5:e15535.
215. Hamada S., Kim T.D., Suzuki T., Itoh Y., Tsumoto H., Nakagawa H., et al. Synthesis and activity of N-oxalylglycine and its derivatives as Jumonji C-domain-containing histone lysine demethylase inhibitors. Bioorg Med Chem Lett 2009, 19:2852-2855.