Structure-based identification of drug-like inhibitors of p300 histone acetyltransferase

Yaoxue Xuebao

Volumn 48, Issue 5, 2013, Pages 700-708

  Zeng, Fan Qi ^a   Peng, Shi Ming ^b   Li, Li ^b   Mu, Li Bing ^b   Zhang, Zhen Hua ^b   Zhang, Zhi Yuan ^b   Huang, Niu ^b  

^a CHONGQING UNIVERSITY OF TECHNOLOGY   (China)

^b NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES   (China)

Author keywords

Drug like; Histone acetyltransferase; Lead optimization; Molecular docking; Structure based drug design

Indexed keywords

4 ACETYL 2 METHYL N MORPHOLINO 3,4 DIHYDRO 3H BENZON[B][1,4]THIAZINE-7SULFONAMIDE; P300 HISTONE ACETYLTRANSFERASE INHIBITOR; SULFONAMIDE; TRANSFERASE INHIBITOR; UNCLASSIFIED DRUG; 4-ACETYL-2-METHYL-N-MORPHOLINO-3,4-DIHYDRO-2H-BENZO(B)(1,4)THIAZINE-7-SULFONAMIDE; ENZYME INHIBITOR; HISTONE ACETYLTRANSFERASE PCAF; MORPHOLINE DERIVATIVE;

ARTICLE; DRUG SCREENING; STRUCTURE ACTIVITY RELATION; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; SYNTHESIS;

DRUG DESIGN; ENZYME INHIBITORS; MOLECULAR STRUCTURE; MORPHOLINES; P300-CBP TRANSCRIPTION FACTORS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84879927564     PISSN: 05134870     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. Allfrey VG, Faulkner R, Mirsky AE. Acetylation and methylation of histones and their possible role in the regulation of RNA synthesis [J]. Proc Natl Acad Sci USA, 1964, 51: 786-794.
2. Kouzarides T. Chromatin modifications and their function [J]. Cell, 2007, 128: 693-705. (Pubitemid 46273577)
3. Zhao S, Xu W, Jiang W, et al. Regulation of cellular metabolism by protein lysine acetylation [J]. Science, 2010, 327: 1000-1004.
4. Sterner DE, Berger SL. Acetylation of histones and transcription-related factors [J]. Microbiol Mol Biol Rev, 2000, 64: 435-459. (Pubitemid 30412680)
5. Monneret C. Histone deacetylase inhibitors for epigenetic therapy of cancer [J]. Anticancer Drugs, 2007, 18: 363-370. (Pubitemid 46712399)
6. Frank JD, Hidde JH. Histone acetyl transferases as emerging drug targets [J]. Drug Discov Today, 2009, 14: 942-948.
7. Arif M, Vedamurthy BM, Choudhari R, et al. Nitric oxide-mediated histone hyperacetylation in oral cancer: target for a water-soluble HAT inhibitor, CTK7A [J]. J Chem Biol, 2010, 17: 903-913.
8. Bowers EM, Yan G, Mukherjee C, et al. Virtual ligand screening of the p300/CBP histone acetyltransferase: identification of a selective small molecule inhibitor [J]. J Chem Biol, 2010, 17: 471-482.
9. Liu X, Wang L, Zhao K, et al. The structural basis of protein acetylation by the p300/CBP transcriptional coactivator [J]. Nature, 2008, 451: 846-850. (Pubitemid 351253165)
10. Lau OD, Kundu TK, Soccio RE, et al. HATs off: selective synthetic inhibitors of the histone acetyltransferases p300 and PCAF [J]. Mol Cell, 2000, 5: 589-595.
11. Balasubramanyam K, Swaminathan V, Ranganathan A, et al. Small molecule modulators of histone acetyltransferase p300 [J]. J Biol Chem, 2003, 278: 19134-19140. (Pubitemid 36799302)
12. Eliseeva ED, Valkov V, Jung M, et al. Characterization of novel inhibitors of histone acetyltransferases [J]. Mol Cancer Ther, 2007, 6: 2391-2398. (Pubitemid 47480404)
13. Balasubramanyam K, Varier RA, Altaf M, et al. Curcumin, a novel p300/CREB-binding protein-specific inhibitor of acetytransferase, represses the acetylation of histone/nonhistone proteins and histone acetyltransferase- dependent chromatin transcription [J]. J Biol Chem, 2004, 279: 51163-51171. (Pubitemid 40017859)
14. Sarli V, Giannis A. Selective Inhibition of CBP/p300 HAT [J]. J Chem Biol, 2007, 14: 605-606.
15. Gorsuch S, Bavetsias V, Rowlands MG, et al. Synthesis of isothiazol-3-one derivatives as inhibitors of histone acetyltransferases (HATs) [J]. Bioorg Med Chem, 2009, 17: 467-474.
16. Baell JB, Holloway GA. New substructure filters for removal of pan assay interference compounds (PAINS) from screening libraries and for their exclusion in bioassays [J]. J Med Chem, 2010, 53: 2719-2740.
17. Yang F, Jin L, Huang NY, et al. Design, synthesis and activity of a new type of influenza virus N1 neuraminidase inhibitors [J]. Acta Pharm Sin, 2011, 46: 1344-1348.
18. Zhang YD, Cai YN, Zhang Q, et al. Inhibitory effect of icariin on acetylcholine-esterase [J]. Acta Pharm Sin, 2012, 47: 1141-1146.
19. Sonawane LV, Bari SB. QSAR, docking studies and pharmacophore identification of phenylmethyl phenoxy propyl amino propanoic acid derivatives as leukotriene A4 hydrolase inhibitors [J]. Acta Pharm Sin, 2010, 45: 615-623.
20. Huang N, Nagarsekar A, Xia GJ, et al. Identification of non-phosphate-containing small molecular weight inhibitors of the tyrosine kinase p56 Lck SH2 domain via in silico screening against the pY+3 binding site [J]. J Med Chem, 2004, 47: 3502-3511. (Pubitemid 38822012)
21. Huang N, Jacobson MP. Binding-site assessment by virtual fragment screening [J]. PLoS One, 2010, 5: e10109.
22. Lorber DM, Shoichet BK. Hierarchical docking of databases of multiple ligand conformations [J]. J Curr Top Med Chem, 2005, 5: 739-749. (Pubitemid 41179714)
23. Huang N, Shoichet BK, Irwin JJ. Benchmarking sets for molecular docking [J]. J Med Chem, 2006, 49: 6789-6801. (Pubitemid 44749746)
24. Huang N, Kalyanaraman C, Irwin JJ, et al. Physics-based scoring of protein-ligand complexes: enrichment of known inhibitors in large-scale virtual screening [J]. J Chem Inf Model, 2006, 46: 243-253. (Pubitemid 43282119)
25. Huang N, Kalyanaraman C, Bernacki K, et al. Molecular mechanics methods for predicting protein-ligand binding [J]. Phys Chem Chem Phys, 2006, 8: 5166-5177.
26. Kollman PA, Massova I, Reyes C, et al. Calculating structures and free energies of complex molecules: combining molecular mechanics and continuum models [J]. Acc Chem Res, 2000, 33: 889-897. (Pubitemid 32056774)
27. Surleraux DLNG, de Kock HA, Verschueren WG, et al. Design of HIV-1 protease inhibitors active on multidrug-resistant virus [J]. J Med Chem, 2005, 48: 1965-1973. (Pubitemid 40403065)
28. Kamila S, Koh B, Khan O, et al. Regioselective one pot synthesis of 2-alkyl/aryl-4H-benzo[1, 4]thiazine-3-one via microwave irradiation [J]. J Heterocycl Chem, 2006, 43: 1641-1646. (Pubitemid 44907064)
29. Pettersen EF, Goddard TD, Huang CC, et al. UCSF Chimera - a visualization system for exploratory research and analysis [J]. J Comput Chem, 2004, 25: 1605-1612.
30. Karukurichi KR, Wang L, Uzasci L, et al. Analysis of p300/CBP histone acetyltransferase regulation using circular permutation and semisynthesis [J]. J Am Chem Soc, 2010, 132: 1222-1223.