메뉴 건너뛰기




Volumn 53, Issue 14, 2010, Pages 5197-5212

(Bis)urea and (Bis)thiourea inhibitors of lysine-specific demethylase 1 as epigenetic modulators

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME; ENZYME INHIBITOR; LYSINE SPECIFIC DEMETHYLASE 1; LYSINE SPECIFIC DEMETHYLASE 1 INHIBITOR; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

EID: 77954691054     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100217a     Document Type: Article
Times cited : (130)

References (54)
  • 2
    • 1842411320 scopus 로고    scopus 로고
    • Crystal structure of the nucleosome core particle at 2.8 A resolution
    • Luger, K.; Mader, A. W.; Richmond, R. K.; Sargent, D. F.; Richmond, T. J. Crystal structure of the nucleosome core particle at 2.8 A resolution Nature 1997, 389 (6648) 251-260
    • (1997) Nature , vol.389 , Issue.6648 , pp. 251-260
    • Luger, K.1    Mader, A.W.2    Richmond, R.K.3    Sargent, D.F.4    Richmond, T.J.5
  • 3
    • 0035839136 scopus 로고    scopus 로고
    • Translating the histone code
    • Jenuwein, T.; Allis, C. D. Translating the histone code Science 2001, 293 (5532) 1074-1080
    • (2001) Science , vol.293 , Issue.5532 , pp. 1074-1080
    • Jenuwein, T.1    Allis, C.D.2
  • 4
    • 0036527775 scopus 로고    scopus 로고
    • Histone-deacetylase inhibitors: Novel drugs for the treatment of cancer
    • Johnstone, R. W. Histone-deacetylase inhibitors: novel drugs for the treatment of cancer Nature Rev. Drug Discovery 2002, 1 (4) 287-299
    • (2002) Nature Rev. Drug Discovery , vol.1 , Issue.4 , pp. 287-299
    • Johnstone, R.W.1
  • 5
    • 0345357773 scopus 로고    scopus 로고
    • Gene silencing in cancer in association with promoter hypermethylation
    • Herman, J. G.; Baylin, S. B. Gene silencing in cancer in association with promoter hypermethylation N. Engl. J. Med. 2003, 349 (21) 2042-2054
    • (2003) N. Engl. J. Med. , vol.349 , Issue.21 , pp. 2042-2054
    • Herman, J.G.1    Baylin, S.B.2
  • 6
    • 0035962631 scopus 로고    scopus 로고
    • DNA methylation, methyltransferases, and cancer
    • Robertson, K. D. DNA methylation, methyltransferases, and cancer Oncogene 2001, 20 (24) 3139-3155
    • (2001) Oncogene , vol.20 , Issue.24 , pp. 3139-3155
    • Robertson, K.D.1
  • 7
    • 32444434989 scopus 로고    scopus 로고
    • Histone H4-K16 Acetylation Controls Chromatin Structure and Protein Interactions
    • Shogren-Knaak, M.; Ishii, H.; Sun, J.-M.; Pazin, M. J.; Davie, J. R.; Peterson, C. L. Histone H4-K16 Acetylation Controls Chromatin Structure and Protein Interactions Science 2006, 311 (5762) 844-847
    • (2006) Science , vol.311 , Issue.5762 , pp. 844-847
    • Shogren-Knaak, M.1    Ishii, H.2    Sun, J.-M.3    Pazin, M.J.4    Davie, J.R.5    Peterson, C.L.6
  • 8
    • 33644846509 scopus 로고    scopus 로고
    • Epigenetic gene silencing in cancer - A mechanism for early oncogenic pathway addiction?
    • Baylin, S. B.; Ohm, J. E. Epigenetic gene silencing in cancer - a mechanism for early oncogenic pathway addiction? Nature Rev. Cancer 2006, 6 (2) 107-116
    • (2006) Nature Rev. Cancer , vol.6 , Issue.2 , pp. 107-116
    • Baylin, S.B.1    Ohm, J.E.2
  • 9
    • 33847065486 scopus 로고    scopus 로고
    • The epigenomics of cancer
    • Jones, P. A.; Baylin, S. B. The epigenomics of cancer Cell 2007, 128 (4) 683-692
    • (2007) Cell , vol.128 , Issue.4 , pp. 683-692
    • Jones, P.A.1    Baylin, S.B.2
  • 10
  • 12
    • 24144475284 scopus 로고    scopus 로고
    • Reversing histone methylation
    • Bannister, A. J.; Kouzarides, T. Reversing histone methylation Nature 2005, 436 (7054) 1103-1106
    • (2005) Nature , vol.436 , Issue.7054 , pp. 1103-1106
    • Bannister, A.J.1    Kouzarides, T.2
  • 13
    • 0036532202 scopus 로고    scopus 로고
    • Histone methylation in transcriptional control
    • Kouzarides, T. Histone methylation in transcriptional control Curr. Opin. Genet. Dev. 2002, 12 (2) 198-209
    • (2002) Curr. Opin. Genet. Dev. , vol.12 , Issue.2 , pp. 198-209
    • Kouzarides, T.1
  • 14
    • 27644589675 scopus 로고    scopus 로고
    • The diverse functions of histone lysine methylation
    • Martin, C.; Zhang, Y. The diverse functions of histone lysine methylation Nature Rev. Mol. Cell Biol. 2005, 6 (11) 838-849
    • (2005) Nature Rev. Mol. Cell Biol. , vol.6 , Issue.11 , pp. 838-849
    • Martin, C.1    Zhang, Y.2
  • 15
    • 0035883954 scopus 로고    scopus 로고
    • Transcription regulation by histone methylation: Interplay between different covalent modifications of the core histone tails
    • Zhang, Y.; Reinberg, D. Transcription regulation by histone methylation: interplay between different covalent modifications of the core histone tails Genes Dev. 2001, 15 (18) 2343-2360
    • (2001) Genes Dev. , vol.15 , Issue.18 , pp. 2343-2360
    • Zhang, Y.1    Reinberg, D.2
  • 16
    • 0036683308 scopus 로고    scopus 로고
    • Unsafe SETs: Histone lysine methyltransferases and cancer
    • Schneider, R.; Bannister, A. J.; Kouzarides, T. Unsafe SETs: histone lysine methyltransferases and cancer Trends Biochem. Sci. 2002, 27 (8) 396-402
    • (2002) Trends Biochem. Sci. , vol.27 , Issue.8 , pp. 396-402
    • Schneider, R.1    Bannister, A.J.2    Kouzarides, T.3
  • 17
    • 33750740754 scopus 로고    scopus 로고
    • Purification of histone demethylases from HeLa cells
    • Tsukada, Y.; Zhang, Y. Purification of histone demethylases from HeLa cells Methods 2006, 40 (4) 318-326
    • (2006) Methods , vol.40 , Issue.4 , pp. 318-326
    • Tsukada, Y.1    Zhang, Y.2
  • 20
    • 33947152396 scopus 로고    scopus 로고
    • The trithorax group protein Lid is a trimethyl histone H3K4 demethylase required for dMyc-induced cell growth
    • Secombe, J.; Li, L.; Carlos, L.; Eisenman, R. N. The trithorax group protein Lid is a trimethyl histone H3K4 demethylase required for dMyc-induced cell growth Genes Dev. 2007, 21 (5) 537-551
    • (2007) Genes Dev. , vol.21 , Issue.5 , pp. 537-551
    • Secombe, J.1    Li, L.2    Carlos, L.3    Eisenman, R.N.4
  • 24
    • 33745187327 scopus 로고    scopus 로고
    • Histone H3 lysine 4 demethylation is a target of nonselective antidepressive medications
    • Lee, M. G.; Wynder, C.; Schmidt, D. M.; McCafferty, D. G.; Shiekhattar, R. Histone H3 lysine 4 demethylation is a target of nonselective antidepressive medications Chem. Biol. 2006, 13 (6) 563-567
    • (2006) Chem. Biol. , vol.13 , Issue.6 , pp. 563-567
    • Lee, M.G.1    Wynder, C.2    Schmidt, D.M.3    McCafferty, D.G.4    Shiekhattar, R.5
  • 26
    • 34250201427 scopus 로고    scopus 로고
    • Lysine-specific demethylase 1 as a potential therapeutic target
    • Stavropoulos, P.; Hoelz, A. Lysine-specific demethylase 1 as a potential therapeutic target Expert Opin. Ther. Targets 2007, 11 (6) 809-820
    • (2007) Expert Opin. Ther. Targets , vol.11 , Issue.6 , pp. 809-820
    • Stavropoulos, P.1    Hoelz, A.2
  • 27
    • 34147173308 scopus 로고    scopus 로고
    • Trans -2-Phenylcyclopropylamine is a mechanism-based inactivator of the histone demethylase LSD1
    • Schmidt, D. M.; McCafferty, D. G. trans -2-Phenylcyclopropylamine is a mechanism-based inactivator of the histone demethylase LSD1 Biochemistry 2007, 46 (14) 4408-4416
    • (2007) Biochemistry , vol.46 , Issue.14 , pp. 4408-4416
    • Schmidt, D.M.1    McCafferty, D.G.2
  • 29
    • 34250203607 scopus 로고    scopus 로고
    • Mechanistic Analysis of a Suicide Inactivator of Histone Demethylase LSD1
    • 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
    • (2007) Biochemistry , vol.46 , pp. 6892-6902
    • Szewczuk, L.M.1    Culhane, J.C.2    Yang, M.3    Majumdar, A.4    Yu, H.5    Cole, P.A.6
  • 30
    • 43549091096 scopus 로고    scopus 로고
    • Facile synthesis of substituted trans -2-arylcyclopropylamine inhibitors of the human histone demethylase LSD1 and monoamine oxidases A and B
    • Gooden, D. M.; Schmidt, D. M.; Pollock, J. A.; Kabadi, A. M.; McCafferty, D. G. Facile synthesis of substituted trans -2-arylcyclopropylamine inhibitors of the human histone demethylase LSD1 and monoamine oxidases A and B Bioorg. Med. Chem. Lett. 2008, 18 (10) 3047-3051
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , Issue.10 , pp. 3047-3051
    • Gooden, D.M.1    Schmidt, D.M.2    Pollock, J.A.3    Kabadi, A.M.4    McCafferty, D.G.5
  • 34
    • 8444237781 scopus 로고    scopus 로고
    • Effect of mitoguazone on polyamine oxidase activity in rat liver
    • Ferioli, M. E.; Berselli, D.; Caimi, S. Effect of mitoguazone on polyamine oxidase activity in rat liver Toxicol. Appl. Pharmacol. 2004, 201 (2) 105-111
    • (2004) Toxicol. Appl. Pharmacol. , vol.201 , Issue.2 , pp. 105-111
    • Ferioli, M.E.1    Berselli, D.2    Caimi, S.3
  • 35
    • 0021255460 scopus 로고
    • General synthetic access to alpha-allenyl amines and alpha-allenyl-alpha- amino acids as potential enzyme activated, irreversible inhibitors of PLP-dependent enzymes
    • Casara, P.; Jund, K.; Bey, P. General synthetic access to alpha-allenyl amines and alpha-allenyl-alpha-amino acids as potential enzyme activated, irreversible inhibitors of PLP-dependent enzymes Tetrahedron Lett. 1984, 25, 1891-1894
    • (1984) Tetrahedron Lett. , vol.25 , pp. 1891-1894
    • Casara, P.1    Jund, K.2    Bey, P.3
  • 38
    • 1642309250 scopus 로고    scopus 로고
    • Molecular basis for the binding of competitive inhibitors of maize polyamine oxidase
    • Cona, A.; Manetti, F.; Leone, R.; Corelli, F.; Tavladoraki, P.; Polticelli, F.; Botta, M. Molecular basis for the binding of competitive inhibitors of maize polyamine oxidase Biochemistry 2004, 43 (12) 3426-3435
    • (2004) Biochemistry , vol.43 , Issue.12 , pp. 3426-3435
    • Cona, A.1    Manetti, F.2    Leone, R.3    Corelli, F.4    Tavladoraki, P.5    Polticelli, F.6    Botta, M.7
  • 39
    • 33845664843 scopus 로고    scopus 로고
    • Inhibition of plant amine oxidases by a novel series of diamine derivatives
    • Stranska, J.; Sebela, M.; Tarkowski, P.; Rehulka, P.; Chmelik, J.; Popa, I.; Pec, P. Inhibition of plant amine oxidases by a novel series of diamine derivatives Biochimie 2007, 89 (1) 135-144
    • (2007) Biochimie , vol.89 , Issue.1 , pp. 135-144
    • Stranska, J.1    Sebela, M.2    Tarkowski, P.3    Rehulka, P.4    Chmelik, J.5    Popa, I.6    Pec, P.7
  • 40
    • 33646178978 scopus 로고    scopus 로고
    • Novel alkylpolyaminoguanidines and alkylpolyaminobiguanides with potent antitrypanosomal activity
    • 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 (12) 3229-3232
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , Issue.12 , pp. 3229-3232
    • Bi, X.1    Lopez, C.2    Bacchi, C.J.3    Rattendi, D.4    Woster, P.M.5
  • 41
    • 0027407457 scopus 로고
    • Chemistry of chlorocarbonyl isocyanate
    • Gorbatenko, V. I. Chemistry of chlorocarbonyl isocyanate Tetrahedron 1993, 49 (16) 3227-3257
    • (1993) Tetrahedron , vol.49 , Issue.16 , pp. 3227-3257
    • Gorbatenko, V.I.1
  • 43
    • 34248561378 scopus 로고    scopus 로고
    • Isothiocyanates from tosyl chloride mediated decomposition of in situ generated dithiocarbamic acid salts
    • Wong, R.; Dolman, S. J. Isothiocyanates from tosyl chloride mediated decomposition of in situ generated dithiocarbamic acid salts J. Org. Chem. 2007, 72 (10) 3969-3971
    • (2007) J. Org. Chem. , vol.72 , Issue.10 , pp. 3969-3971
    • Wong, R.1    Dolman, S.J.2
  • 44
    • 0001604684 scopus 로고
    • Tert -Butoxycarbonylation of Amino Acids and Their Derivatives: N - Tert -Butoxycarbonyl- l -Phenylalanine
    • Keller, O.; Keller, W. E.; van Look, G.; Wersin, G. tert -Butoxycarbonylation of Amino Acids and Their Derivatives: N-tert -Butoxycarbonyl- l -Phenylalanine Org. Synth. 1985, 63, 160-171
    • (1985) Org. Synth. , vol.63 , pp. 160-171
    • Keller, O.1    Keller, W.E.2    Van Look, G.3    Wersin, G.4
  • 46
    • 0001586711 scopus 로고
    • Synthesis and reactions of N -chlorocarbonyl isocyanate
    • Hagemann, H. Synthesis and reactions of N -chlorocarbonyl isocyanate Angew. Chem., Intl. Ed. Engl. 1977, 16, 743-750
    • (1977) Angew. Chem., Intl. Ed. Engl. , vol.16 , pp. 743-750
    • Hagemann, H.1
  • 48
    • 77949432014 scopus 로고    scopus 로고
    • PHF8, a gene associated with cleft lip/palate and mental retardation, encodes for an Nepsilon-dimethyl lysine demethylase
    • Loenarz, C.; Ge, W.; Coleman, M. L.; Rose, N. R.; Cooper, C. D.; Klose, R. J.; Ratcliffe, P. J.; Schofield, C. J. PHF8, a gene associated with cleft lip/palate and mental retardation, encodes for an Nepsilon-dimethyl lysine demethylase Hum. Mol. Genet. 2010, 19 (2) 217-222
    • (2010) Hum. Mol. Genet. , vol.19 , Issue.2 , pp. 217-222
    • Loenarz, C.1    Ge, W.2    Coleman, M.L.3    Rose, N.R.4    Cooper, C.D.5    Klose, R.J.6    Ratcliffe, P.J.7    Schofield, C.J.8
  • 50
    • 26444441453 scopus 로고    scopus 로고
    • Alkyl-substituted polyaminohydroxamic acids: A novel class of targeted histone deacetylase inhibitors
    • Varghese, S.; Gupta, D.; Baran, T.; Jiemjit, A.; Gore, S. D.; Casero, R. A., Jr.; Woster, P. M. Alkyl-substituted polyaminohydroxamic acids: a novel class of targeted histone deacetylase inhibitors J. Med. Chem. 2005, 48 (20) 6350-6365
    • (2005) J. Med. Chem. , vol.48 , Issue.20 , pp. 6350-6365
    • Varghese, S.1    Gupta, D.2    Baran, T.3    Jiemjit, A.4    Gore, S.D.5    Casero Jr., R.A.6    Woster, P.M.7
  • 51
  • 52
    • 73449126835 scopus 로고    scopus 로고
    • MS275 enhances cytotoxicity induced by 5-fluorouracil in the colorectal cancer cells
    • Flis, S.; Gnyszka, A.; Flis, K.; Splawinski, J. MS275 enhances cytotoxicity induced by 5-fluorouracil in the colorectal cancer cells Eur. J. Pharmacol. 2010, 627 (1-3) 26-32
    • (2010) Eur. J. Pharmacol. , vol.627 , Issue.1-3 , pp. 26-32
    • Flis, S.1    Gnyszka, A.2    Flis, K.3    Splawinski, J.4
  • 53
    • 33750036141 scopus 로고    scopus 로고
    • Histone deacetylase inhibitors in cancer therapy
    • Fouladi, M. Histone deacetylase inhibitors in cancer therapy Cancer Invest. 2006, 24 (5) 521-527
    • (2006) Cancer Invest. , vol.24 , Issue.5 , pp. 521-527
    • Fouladi, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.