Virtual Ligand Screening of the p300/CBP Histone Acetyltransferase: Identification of a Selective Small Molecule Inhibitor
Tài liệu tham khảo
Abagyan, 1994, ICM—a new method for protein modeling and design: applications to docking and structure prediction from the distorted native conformation, J. Comput. Chem., 15, 488, 10.1002/jcc.540150503
Arif, 2009, Mechanism of p300 specific histone acetyltransferase inhibition by small molecules, J. Med. Chem., 52, 267, 10.1021/jm800657z
Balasubramanyam, 2003, Small molecule modulators of histone acetyltransferase p300, J. Biol. Chem., 278, 19134, 10.1074/jbc.M301580200
Balasubramanyam, 2004, Curcumin, a novel p300/CREB-binding protein-specific inhibitor of acetyltransferase, represses the acetylation of histone/nonhistone proteins and histone acetyltransferase-dependent chromatin transcription, J. Biol. Chem., 279, 51163, 10.1074/jbc.M409024200
Bannister, 1996, The CBP co-activator is a histone acetyltransferase, Nature, 384, 641, 10.1038/384641a0
Bisson, 2009, Modeling of the aryl hydrocarbon receptor (AhR) ligand binding domain and its utility in virtual ligand screening to predict new AhR ligands, J. Med. Chem., 52, 5635, 10.1021/jm900199u
Cavasotto, 2008, Discovery of novel chemotypes to a G-protein-coupled receptor through ligand-steered homology modeling and structure-based virtual screening, J. Med. Chem., 51, 581, 10.1021/jm070759m
Choudhary, 2009, Lysine acetylation targets protein complexes and co-regulates major cellular functions, Science, 325, 834, 10.1126/science.1175371
Clayton, 2000, Phosphoacetylation of histone H3 on c-fos- and c-jun-associated nucleosomes upon gene activation, EMBO J., 19, 3714, 10.1093/emboj/19.14.3714
Cole, 2008, Chemical probes for histone-modifying enzymes, Nat. Chem. Biol., 4, 590, 10.1038/nchembio.111
Copeland, 2000
Dekker, 2009, Histone acetyl transferases as emerging drug targets, Drug Discov. Today, 14, 942, 10.1016/j.drudis.2009.06.008
Delaglio, 1995, NMRPipe: a multidimensional spectral processing system based on UNIX pipes, J. Biomol. NMR, 6, 277, 10.1007/BF00197809
Edmunds, 2008, Dynamic histone H3 methylation during gene induction: HYPB/Setd2 mediates all H3K36 trimethylation, EMBO J., 27, 406, 10.1038/sj.emboj.7601967
Feng, 2005, High-throughput assays for promiscuous inhibitors, Nat. Chem. Biol., 1, 146, 10.1038/nchembio718
Goodman, 2000, CBP/p300 in cell growth, transformation, and development, Genes Dev., 14, 1553, 10.1101/gad.14.13.1553
Gu, 1997, Activation of p53 sequence-specific DNA binding by acetylation of the p53 C-terminal domain, Cell, 90, 595, 10.1016/S0092-8674(00)80521-8
Guidez, 2005, Histone acetyltransferase activity of p300 is required for transcriptional repression by the promyelocytic leukemia zinc finger protein, Mol. Cell. Biol., 25, 5552, 10.1128/MCB.25.13.5552-5566.2005
Haberland, 2009, The many roles of histone deacetylases in development and physiology: implications for disease and therapy, Nat. Rev. Genet., 10, 32, 10.1038/nrg2485
Halgren, 1996, Merck molecular force field. IV. Conformational energies and geometries for MMFF94, J. Comput. Chem., 17, 587, 10.1002/(SICI)1096-987X(199604)17:5/6<587::AID-JCC4>3.0.CO;2-Q
Hodawadekar, 2007, Chemistry of acetyl transfer by histone modifying enzymes: structure, mechanism and implications for effector design, Oncogene, 26, 5528, 10.1038/sj.onc.1210619
Hodgkiss, 1991, Fluorescent markers for hypoxic cells. A study of novel heterocyclic compounds that undergo bio-reductive binding, Biochem. Pharmacol., 41, 533, 10.1016/0006-2952(91)90625-F
Holbert, 2007, The human monocytic leukemia zinc finger histone acetyltransferase domain contains DNA-binding activity implicated in chromatin targeting, J. Biol. Chem., 282, 36603, 10.1074/jbc.M705812200
Hosoya, 2003, Dantrolene analogues revisited: General synthesis and specific functions capable of discriminating two kinds of Ca2+ release from sarcoplasmic reticulum of mouse skeletal muscle, Bioorg. Med. Chem., 11, 663, 10.1016/S0968-0896(02)00600-4
Itoh, 2008, Isoform-selective histone deacetylase inhibitors, Curr. Pharm. Des., 14, 529, 10.2174/138161208783885335
Iyer, 2007, p300 is required for orderly G1/S transition in human cancer cells, Oncogene, 26, 21, 10.1038/sj.onc.1209771
Kim, 1991, Peptide synthesis with polymer bound active ester. II Synthesis of pyrazolone resin and its applications in acylation reaction, Bull. Korean Chem. Soc., 12, 376
Kim, 2000, A continuous, nonradioactive assay for histone acetyltransferases, Anal. Biochem., 280, 308, 10.1006/abio.2000.4546
Kitz, 1962, Esters of methanesulfonic acid as irreversible inhibitors of acetylcholinesterase, J. Biol. Chem., 237, 3245, 10.1016/S0021-9258(18)50153-8
Langner, 2005, Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-Aldol reactions, Chem. Eur. J., 11, 6254, 10.1002/chem.200500497
Lau, 2000, p300/CBP-associated factor histone acetyltransferase processing of a peptide substrate. Kinetic analysis of the catalytic mechanism, J. Biol. Chem., 275, 1953, 10.1074/jbc.M003219200
Lau, 2000, HATs off: selective synthetic inhibitors of the histone acetyltransferases p300 and PCAF, Mol. Cell, 5, 589, 10.1016/S1097-2765(00)80452-9
Liu, 2008, The structural basis of protein acetylation by the p300/CBP transcriptional coactivator, Nature, 451, 846, 10.1038/nature06546
Liu, 2008, A fasting inducible switch modulates gluconeogenesis via activator/coactivator exchange, Nature, 456, 269, 10.1038/nature07349
Macek, 2009, Global and site-specific quantitative phosphoproteomics: principles and applications, Annu. Rev. Pharmacol. Toxicol., 49, 199, 10.1146/annurev.pharmtox.011008.145606
Mallya, 2007, Small molecules block the polymerization of Z alpha1-antitrypsin and increase the clearance of intracellular aggregates, J. Med. Chem., 50, 5357, 10.1021/jm070687z
Mantelingu, 2007, Specific inhibition of p300-HAT alters global gene expression and represses HIV replication, Chem. Biol., 14, 645, 10.1016/j.chembiol.2007.04.011
Moreau, 2008, Discovery of new Gram-negative antivirulence drugs: structure and properties of novel E. coli WaaC inhibitors, Bioorg. Med. Chem. Lett., 18, 4022, 10.1016/j.bmcl.2008.05.117
Nemethy, 1992, Energy parameters in polypeptides. 10. Improved geometrical parameters and nonbonded interactions for use in the ECEPP/3 algorithm, with application to proline-containing peptides, J. Phys. Chem., 96, 6472, 10.1021/j100194a068
Ogryzko, 1996, The transcriptional coactivators p300 and CBP are histone acetyltransferases, Cell, 87, 953, 10.1016/S0092-8674(00)82001-2
Poux, 2002, Structure of the GCN5 histone acetyltransferase bound to a bisubstrate inhibitor, Proc. Natl. Acad. Sci. USA, 99, 14065, 10.1073/pnas.222373899
Qiao, 2006, Chemical rescue of a mutant enzyme in living cells, Science, 311, 1293, 10.1126/science.1122224
Ravindra, 2009, Inhibition of lysine acetyltransferase KAT3B/p300 activity by a naturally occurring hydroxynaphthoquinone, plumbagin, J. Biol. Chem., 284, 24453, 10.1074/jbc.M109.023861
Robinson, J.P., editor. (2009). Current Protocols in Cytometry (New York: Wiley Interscience), Online ISSN 1934-9300.
Shechter, 2007, Extraction, purification and analysis of histones, Nat. Protoc., 2, 1445, 10.1038/nprot.2007.202
Shia, 2005, Characterization of the yeast trimeric-SAS acetyltransferase complex, J. Biol. Chem., 280, 11987, 10.1074/jbc.M500276200
Shogren-Knaak, 2001, Recent advances in chemical approaches to the study of biological systems, Annu. Rev. Cell Dev. Biol., 17, 405, 10.1146/annurev.cellbio.17.1.405
Stimson, 2005, Isothiazolones as inhibitors of PCAF and p300 histone acetyltransferase activity, Mol. Cancer Ther., 4, 1521, 10.1158/1535-7163.MCT-05-0135
Sutton, 2003, Sas4 and Sas5 are required for the histone acetyltransferase activity of Sas2 in the SAS complex, J. Biol. Chem., 278, 16887, 10.1074/jbc.M210709200
Szewczuk, 2007, De novo discovery of serotonin N-acetyltransferase inhibitors, J. Med. Chem., 50, 5330, 10.1021/jm0706463
Tang, 2008, Fungal Rtt109 histone acetyltransferase is an unexpected structural homolog of metazoan p300/CBP, Nat. Struct. Mol. Biol., 15, 738, 10.1038/nsmb.1448
Thomson, 1999, The nucleosomal response associated with immediate-early gene induction is mediated via alternative MAP kinase cascades: MSK1 as a potential histone H3/HMG-14 kinase, EMBO J., 18, 4779, 10.1093/emboj/18.17.4779
Thompson, 2001, Transcriptional coactivator protein p300. Kinetic characterization of its histone acetyltransferase activity, J. Biol. Chem., 276, 33721, 10.1074/jbc.M104736200
Thompson, 2004, Regulation of the p300 HAT domain via a novel activation loop, Nat. Struct. Mol. Biol., 11, 308, 10.1038/nsmb740
Totrov, 1997, Flexible protein–ligand docking by global energy optimization in internal coordinates, Proteins, 1, 215, 10.1002/(SICI)1097-0134(1997)1+<215::AID-PROT29>3.0.CO;2-Q
Totrov, M., and Abagyan, R. (1999). Derivation of sensitive discrimination potential for virtual ligand screening. Proceedings of the Third Annual International Conference on Computational Molecular Biology, 312–320.
Vasyunkina, 2005, Synthesis of 1,4-dihydropyrano[2,3-c]pyrazole derivatives, Russ. J. Org. Chem., 41, 742, 10.1007/s11178-005-0236-5
Walsh, 2006
Wang, 2008, Structure and chemistry of the p300/CBP and Rtt109 histone acetyltransferases: implications for histone acetyltransferase evolution and function, Curr. Opin. Struct. Biol., 18, 741, 10.1016/j.sbi.2008.09.004
Yang, 2008, Lysine acetylation: codified crosstalk with other posttranslational modifications, Mol. Cell, 31, 449, 10.1016/j.molcel.2008.07.002
Yoshida, 1990, Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A, J. Biol. Chem., 265, 17174, 10.1016/S0021-9258(17)44885-X
Yu, 2006, Bisubstrate inhibition: Theory and application to N-acetyltransferases, Biochemistry, 45, 14788, 10.1021/bi061621t
Zheng, 2005, Synthesis and evaluation of a potent and selective cell-permeable p300 histone acetyltransferase inhibitor, J. Am. Chem. Soc., 127, 17182, 10.1021/ja0558544