Modulation of the activity of histone acetyltransferases by long chain alkylidenemalonates (LoCAMs)
CNR Ibb | back to homepage
▲NavBar
Ricerca avanzata▼
Contiene: [X]      Estesa     Autori: [X]  Tipo di lavoro: [X]   Data iniziale: Data finale: [X]      Sede: Affiliazione IBB     
    
[Pulisci modulo]


Modulation of the activity of histone acetyltransferases by long chain alkylidenemalonates (LoCAMs) (134 visite)

Milite C, Castellano S, Benedetti R, Tosco A, Ciliberti C, Vicidomini C, Boully L, Franci G, Altucci L, Mai A, Sbardella G

Bioorg Med Chem (ISSN: 0968-0896, 1464-3391, 1464-3391electronic), 2011 Jun 15; 19(12): 3690-3701.



Tipo di articolo: Journal Article,

Impact factor: 2.921, Impact factor a 5 anni: 3.157

Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-79958265044&partnerID=40&md5=60b1cedc8aacbaba9aa0db197b88db75

Parole chiave: Epigenetics, Histone Acetyltransferases Modulators, Kat, P300 Cbp, Pcaf Activator, 2 Dodecylmalonic Acid, 2 Tridecylmalonic Acid, 2 Undecylmalonic Acid, 2 Dimethyl 5 Pentadecyl 1, 3 Dioxane 4, 6 Dione, 2 Dimethyl 5 Pentadecylidene 1, Alkan 2 Ylidene Malonic Acid Derivative, Diethyl 2 (1 Aminopentadecylidene)malonic Acid, Diethyl 2 (1 Chloropentadecylidene)malonic Acid, Diethyl 2 (1 Hydroxyheptadecylidene)malonic Acid, Diethyl 2 (1 Hydroxyhexadecylidene)malonic Acid, Diethyl 2 (1 Hydroxypentadecylidene)malonic Acid, Diethyl 2 [(tridecylamino)methylene]malonic Acid Derivative, Diethyl 2 Pentadecylidenemalonic Acid, Diethyl 2 Tetradecylidenemalonic Acid, Diethyl 2 Tridecylmalonic Acid, Enzyme Inhibitor, Functional Group, Long Chain Alkylidenemalonic Acid Derivative, Myristyl Aldehyde, Pentadecanal, Pentadecylmalonic Acid, Tetradecylmalonic Acid, Unclassified Drug, Apoptosis, Article, Biological Activity, Cancer Cell, Cell Cycle, Concentration Response, Controlled Study, Drug Synthesis, Enzyme Activity, Enzyme Induction, Enzyme Inhibition, Enzyme Mechanism, Enzyme Regulation, Histone Acetylation, Human, Human Cell, Leukemia Cell, Protein Expression, Protein Interaction, Protein Modification, Protein Purification, Rigidity, Structure Activity Relation, Alkylation, Blotting, Western, Cell Line, Tumor, Enzyme Activation, Malonates, U937 Cells, Diethyl 2 (1 Aminopentadecylidene) Malonic Acid, Diethyl 2 (1 Chloropentadecylidene) Malonic Acid, Diethyl 2 (1 Hydroxyheptadecylidene) Malonic Acid, Diethyl 2 (1 Hydroxyhexadecylidene) Malonic Acid, Diethyl 2 (1 Hydroxypentadecylidene) Malonic Acid, Diethyl 2 [(tridecylamino) Methylene] Malonic Acid Derivative,

Affiliazioni:

*** IBB - CNR ***
Dipartimento di Scienze Farmaceutiche, Università Degli Studi di Salerno, Via Ponte Don Melillo, 84084 Fisciano (SA), Italy
Dipartimento di Patologia Generale, Seconda Università Degli Studi di Napoli, Vico L. De Crecchio 7, 80138 Napoli, Italy
Dipartimento di Fisica, Università di Napoli Federico II, Napoli, Italy
IGB-CNR, Via Pietro Castellino, 80100, Napoli, Italy
Dipartimento di Chimica e Tecnologie Del Farmaco, Istituto Pasteur-Fondazione Cenci Bolognetti, Sapienza Università di Roma, P.le A. Moro 5, 00185 Roma, Italy


Riferimenti:

Kouzarides, T., (2007) Cell, 128, p. 69

Berger, S.L., (2007) Nature, 447, p. 407

Ruthenburg, A.J., Li, H., Patel, D.J., Allis, C.D., (2007) Nat. Rev. Mol. Cell Biol., 8, p. 983

Strahl, B.D., Allis, C.D., (2000) Nature, 403, p. 41

Allfrey, V.G., Faulkner, R., Mirsky, A.E., (1964) Proc. Natl. Acad. Sci. U.S.A., 51, p. 786

Roth, S.Y., Denu, J.M., Allis, C.D., (2001) Annu. Rev. Biochem., 70, p. 81

Yang, X.-J., Seto, E., (2008) Mol. Cell, 31, p. 449

Liu, Y., Colosimo, A.L., Yang, X.-J., Liao, D., (2000) Mol. Cell. Biol., 20, p. 5540

Hubbert, C., Guardiola, A., Shao, R., Kawaguchi, Y., Ito, A., Nixon, A., Yoshida, M., Yao, T.-P., (2002) Nature, 417, p. 455

Glozak, M.A., Sengupta, N., Zhang, X., Seto, E., (2005) Gene, 363, p. 15

Matthias, P., Yoshida, M., Khochbin, S., (2008) Cell Cycle, 7, p. 7

Arif, M., Selvi, B.R., Kundu, T.K., (2010) ChemBioChem, 11, p. 1501

Von Wantoch Rekowski, M., Giannis, A., (2010) Biochim. Biophys. Acta, Gene Regul. Mech., 1799, p. 760

Zhao, S., Xu, W., Jiang, W., Yu, W., Lin, Y., Zhang, T., Yao, J., Guan, K.-L., (2010) Science, 327, p. 1000

Wang, Q., Zhang, Y., Yang, C., Xiong, H., Lin, Y., Yao, J., Li, H., Zhao, G.-P., (2010) Science, 327, p. 1004

Allis, C.D., Berger, S.L., Cote, J., Dent, S., Jenuwien, T., Kouzarides, T., Pillus, L., Zhang, Y., (2007) Cell, 131, p. 633

Lysine acetylation was initially identified in histones, so many KATs and KDACs are often referred to as histone acetyltransferases (HATs) and deacetylases (HDACs), respectivelyDekker, F.J., Haisma, H.J., (2009) Drug Discovery Today, 14, p. 942

Manzo, F., Tambaro, F.P., Mai, A., Altucci, L., (2009) Expert Opin. Ther. Pat., 19, p. 761

Howe, L., Auston, D., Grant, P., John, S., Cook, R.G., Workman, J.L., Pillus, L., (2001) Genes Dev., 15, p. 3144

Gayther, S.A., Batley, S.J., Linger, L., Bannister, A., Thorpe, K., Chin, S.-F., Daigo, Y., Caldas, C., (2000) Nat. Genet., 24, p. 300

Bandyopadhyay, D., Okan, N.A., Bales, E., Nascimento, L., Cole, P.A., Medrano, E.E., (2002) Cancer Res., 62, p. 6231

Giordano, A., Avantaggiati, M.L., (1999) J. Cell. Physiol., 181, p. 218

Pfister, S., Rea, S., Taipale, M., Mendrzyk, F., Straub, B., Ittrich, C., Thuerigen, O., Lichter, P., (2008) Int. J. Cancer, 122, p. 1207

Katsumoto, T., Yoshida, N., Kitabayashi, I., (2008) Cancer Sci., 99, p. 1523

Iyer, N.G., Xian, J., Chin, S.F., Bannister, A.J., Daigo, Y., Aparicio, S., Kouzarides, T., Caldas, C., (2007) Oncogene, 26, p. 21

Kitabayashi, I., Aikawa, Y., Yokoyama, A., Hosoda, F., Nagai, M., Kakazu, N., Abe, T., Ohki, M., (2001) Leukemia, 15, p. 89

Ait-Si-Ali, S., Polesskaya, A., Filleur, S., Ferreira, R., Duquet, A., Robin, P., Vervish, A., Harel-Bellan, A., (2000) Oncogene, 19, p. 2430

Adcock, I.M., Tsaprouni, L., Bhavsar, P., Ito, K., (2007) Curr. Opin. Immunol., 19, p. 694

Yang, X.J., (2004) Nucleic Acids Res., 32, p. 959

Mantelingu, K., Reddy, B.A.A., Swaminathan, V., Kishore, A.H., Siddappa, N.B., Kumar, G.V.P., Nagashankar, G., Kundu, T.K., (2007) Chem. Biol., 14, p. 645

Barnes, P.J., Adcock, I.M., Ito, K., (2005) Eur. Resp. J., 25, p. 552

Lau, O.D., Kundu, T.K., Soccio, R.E., Ait-Si-Ali, S., Khalil, E.M., Vassilev, A., Wolffe, A.P., Cole, P.A., (2000) Mol. Cell, 5, p. 589

Saha, R.N., Pahan, K., (2005) Cell Death Differ., 13, p. 539

Rouaux, C., Jokic, N., Mbebi, C., Boutillier, S., Loeffler, J.-P., Boutillier, A.-L., (2003) EMBO J., 22, p. 6537

Barrett, R.M., Wood, M.A., (2008) Learn. Memory, 15, p. 460

Maurice, T., Duclot, F., Meunier, J., Naert, G., Givalois, L., Meffre, J., Celerier, A., Gongora, C., (2007) Neuropsychopharmacology, 33, p. 1584

Mai, A., Massa, S., Rotili, D., Cerbara, I., Valente, S., Pezzi, R., Simeoni, S., Ragno, R., (2005) Med. Res. Rev., 25, p. 261

Minucci, S., Pelicci, P.G., (2006) Nat. Rev. Cancer, 6, p. 38

Richon, V.M., Emiliani, S., Verdin, E., Webb, Y., Breslow, R., Rifkind, R.A., Marks, P.A., (1998) Proc. Natl. Acad. Sci. U.S.A., 95, p. 3003

Nakajima, H., Kim, Y.B., Terano, H., Yoshida, M., Horinouchi, S., (1998) Exp. Cell. Res., 241, p. 126

Nagy, Z., Tora, L., (2007) Oncogene, 26, p. 5341

Marmorstein, R., Trievel, R.C., (2009) Biochim. Biophys. Acta, Gene Regul. Mech., 1789, p. 58

Lee, K.K., Workman, J.L., (2007) Nat. Rev. Mol. Cell Biol., 8, p. 284

Hodawadekar, S.C., Marmorstein, R., (2007) Oncogene, 26, p. 5528

Brownell, J.E., Zhou, J., Ranalli, T., Kobayashi, R., Edmondson, D.G., Roth, S.Y., Allis, C.D., (1996) Cell, 84, p. 843

Stockwell, B.R., (2000) Nat. Rev. Genet., 1, p. 116

Bowers, E.M., Yan, G., Mukherjee, C., Orry, A., Wang, L., Holbert, M.A., Crump, N.T., Cole, P.A., (2010) Chem. Biol., 17, p. 471

Cebrat, M., Kim, C.M., Thompson, P.R., Daugherty, M., Cole, P.A., (2003) Bioorg. Med. Chem., 11, p. 3307

Balasubramanyam, K., Swaminathan, V., Ranganathan, A., Kundu, T.K., (2003) J. Biol. Chem., 278, p. 19134

Ravindra, K.C., Selvi, B.R., Arif, M., Reddy, B.A.A., Thanuja, G.R., Agrawal, S., Pradhan, S.K., Kundu, T.K., (2009) J. Biol. Chem., 284, p. 24453

Dal Piaz, F., Tosco, A., Eletto, D., Piccinelli, A.L., Moltedo, O., Franceschelli, S., Sbardella, G., De Tommasi, N., (2010) ChemBioChem, 11, p. 818

Eliseeva, E.D., Valkov, V., Jung, M., Jung, M.O., (2007) Mol. Cancer Ther., 6, p. 2391

Ghizzoni, M., Boltjes, A., Graaf, C.D., Haisma, H.J., Dekker, F.J., (2010) Bioorg. Med. Chem., 18, p. 5826

Souto, J.A., Conte, M., Álvarez, R., Nebbioso, A., Carafa, V., Altucci, L., De Lera, A.R., (2008) ChemMedChem, 3, p. 1435

Costi, R., Di Santo, R., Artico, M., Miele, G., Valentini, P., Novellino, E., Cereseto, A., (2007) J. Med. Chem., 50, p. 1973

Mai, A., Cheng, D., Bedford, M.T., Valente, S., Nebbioso, A., Perrone, A., Brosch, G., Altucci, L., (2008) J. Med. Chem., 51, p. 2279

Dekker, F.J., Ghizzoni, M., Van Der Meer, N., Wisastra, R., Haisma, H.J., (2009) Bioorg. Med. Chem., 17, p. 460

Ghizzoni, M., Haisma, H.J., Dekker, F.J., (2009) Eur. J. Med. Chem., 44, p. 4855

Gorsuch, S., Bavetsias, V., Rowlands, M.G., Aherne, G.W., Workman, P., Jarman, M., McDonald, E., (2009) Bioorg. Med. Chem., 17, p. 467

Stimson, L., Rowlands, M.G., Newbatt, Y.M., Smith, N.F., Raynaud, F.I., Rogers, P., Bavetsias, V., Aherne, G.W., (2005) Mol. Cancer Ther., 4, p. 1521

Biel, M., Kretsovali, A., Karatzali, E., Papamatheakis, J., Giannis, A., (2004) Angew. Chem., Int. Ed., 43, p. 3974

Mai, A., Rotili, D., Tarantino, D., Ornaghi, P., Tosi, F., Vicidomini, C., Sbardella, G., Filetici, P., (2006) J. Med. Chem., 49, p. 6897

Sbardella, G., Castellano, S., Vicidomini, C., Rotili, D., Nebbioso, A., Miceli, M., Altucci, L., Mai, A., (2008) Bioorg. Med. Chem. Lett., 18, p. 2788

Dess, D.B., Martin, J.C., (1991) J. Am. Chem. Soc., 113, p. 7277

Haldar, J., Kondaiah, P., Bhattacharya, S., (2005) J. Med. Chem., 48, p. 3823

Ahlquist, L., Asselineau, C., Asselineau, J., Stallberg-Stenhagen, S., Stenhagen, E., (1958) Ark. Kemi, 31, p. 543

Comeau, D., Lai, R., Charlot, C., Ucciani, E., (1972) Bull. Soc. Chim. Fr., p. 4163

Actually, as noticeable in Figure 5B, a slight acetylation was observed for both compounds at 15 μM concentration. Yet, it was completely undetectable at 30 μMVarier, R.A., Swaminathan, V., Balasubramanyam, K., Kundu, T.K., (2004) Biochem. Pharmacol., 68, p. 1215

In these conditions, compound 2b caused excessive cell deathTurner, B.M., (2005) Nat. Struct. Mol. Biol., 12, p. 110

Mai, A., Esposito, M., Sbardella, G., Massa, S., (2001) Org. Prep. Proced. Int., 33, p. 391

Chang, Y.-H., Uang, B.-J., Wu, C.-M., Yu, T.-H., (1990) Synthesis, 1990, p. 1033

Sorg, G., Mengel, A., Jung, G., Rademann, J., (2001) Angew. Chem., Int. Ed., 40, p. 4395

Kraus, W.L., Kadonaga, J.T., (1998) Genes Dev., 12, p. 331

Nebbioso, A., Clarke, N., Voltz, E., Germain, E., Ambrosino, C., Bontempo, P., Alvarez, R., Altucci, L., (2005) Nat. Med., 11, p. 77

Cooper, M., (2003) Anal. Bioanal. Chem., 377, p. 834

Johnsson, B., Löfs, S., Lindquist, G., (1991) Anal. Biochem., 198, p. 268



A novel class of KAT modulators (long chain alkylidenemalonates, LoCAMs) has been identified. Variations of the alkyl chain length can change the activity profile from inhibition of both KAT3A/KAT2B (as derivative 2a) to the peculiar profile of pentadecylidenemalonate 1b, the first activator/inhibitor of histone acetyltransferases. Together with the powerful apoptotic effect (particularly notable if considering that anacardic acid and other KAT inhibitors are not cell permeable) appoint them as valuable biological tools to understand the mechanisms of lysine acetyltransferases. (C) 2011 Elsevier Ltd. All rights reserved.
Nessun risultato.
Nessun risultato.

Ricerca avanzata▼
Contiene: [X]      Estesa     Autori: [X]  Tipo di lavoro: [X]   Data iniziale: Data finale: [X]      Sede: Affiliazione IBB     
    
[Pulisci modulo]
Vai a fine pagina   Versione per copia e incolla facile   Esporta tutto in BibTeX   Esporta tutto in EndNote


Petraglia F, Singh AA, Carafa V, Nebbioso A, Conte M, Scisciola L, Valente S, Baldi A, Mandoli A, Petrizzi VB, Ingenito C, De Falco S, Cicatiello V, Apicella I, Janssen-megens EM, Kim B, Yi G, Logie C, Heath S, Ruvo M, Wierenga ATJ, Flicek P, Yaspo ML, Della Valle V, Bernard O, Tomassi S, Novellino E, Feoli A, Sbardella G, Gut I, Vellenga E, Stunnenberg HG, Mai A, Martens JHA, Altucci L
* Combined HAT/EZH2 modulation leads to cancer-selective cell death (55 visite)
Oncotarget (ISSN: 1949-2553electronic, 1949-2553linking), 2018 May 22; 9(39): 25630-25646.
Impact Factor: 5.008
Dettagli    Esporta in BibTeX    Esporta in EndNote

Garzia L, Andolfo I, Cusanelli E, Marino N, Petrosino G, De Martino D, Esposito V, Galeone A, Navas L, Esposito S, Gargiulo S, Fattet S, Donofrio V, Cinalli G, Brunetti A, Del Vecchio L, Northcott PA, Delattre O, Taylor MD, Iolascon A, Zollo M
* MicroRNA-199b-5p Impairs Cancer Stem Cells through Negative Regulation of HES1 in Medulloblastoma (175 visite)
Plosone (ISSN: 1932-6203, 1932-6203electronic), 2009 Mar 24; 4(3): e4998-e4998.
Impact Factor: 4.351
Dettagli    Esporta in BibTeX    Esporta in EndNote

Chiechio S, Zammataro M, Morales ME, Busceti CL, Drago F, Th Gereau RW, Copani A, Nicoletti F
* Epigenetic modulation of mGlu2 receptors by histone deacetylase inhibitors in the treatment of inflammatory pain (127 visite)
Mol Pharmacol (ISSN: 0026-895x), 2009; 75(5): 1014-1020.
Impact Factor: 4.531
Dettagli    Esporta in BibTeX    Esporta in EndNote

Sbardella G, Castellano S, Vicidomini C, Rotili D, Nebbioso A, Miceli M, Altucci L, Mai A
* Identification of long chain alkylidenemalonates as novel small molecule modulators of histone acetyltransferases (104 visite)
Bioorganic & Medicinal Chemistry Letters (ISSN: 0960-894x), 2008 May 1; 18(9): 2788-2792.
Impact Factor: 2.531
Dettagli    Esporta in BibTeX    Esporta in EndNote



4 Records (3 escludendo Abstract e Conferenze).
Impact factor totale: 16.421 (12.07 escludendo Abstract e Conferenze).
Impact factor a 5 anni totale: 16.901 (12.518 escludendo Abstract e Conferenze).







    Esporta in BibTeX    Esporta in EndNote