Development of small molecule inhibitors of BRPF1 and TRIM24 bromodomains

Drug Discovery Today: Technologies

Volumn 19, Issue , 2016, Pages 65-71

  Palmer, Wylie S ^a  

^a UNIVERSITY OF TEXAS MD ANDERSON CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL ETHER; BROMODOMAIN AND PHD FINGER CONTAINING PROTEIN FAMILY INHIBITOR; BROMODOMAIN INHIBITOR; TRIPARTITE MOTIF 24 PROTEIN INHIBITOR; UNCLASSIFIED DRUG; BRPF1 PROTEIN, HUMAN; CARRIER PROTEIN; NUCLEAR PROTEIN; SIGNAL TRANSDUCING ADAPTOR PROTEIN; TRIM24 PROTEIN, HUMAN;

DRUG BINDING; DRUG STRUCTURE; EPIGENETICS; HUMAN; NONHUMAN; PROTEIN CONFORMATION; PROTEIN FUNCTION; PROTEIN INTERACTION; REVIEW; SIGNAL TRANSDUCTION; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMISTRY; PROTEIN DOMAIN;

ADAPTOR PROTEINS, SIGNAL TRANSDUCING; ANIMALS; CARRIER PROTEINS; HUMANS; NUCLEAR PROTEINS; PROTEIN DOMAINS;

EID: 84993940430     PISSN: None     EISSN: 17406749     Source Type: Journal    
DOI: 10.1016/j.ddtec.2016.06.005     Document Type: Review

References (49)

1. [1] Filippakopoulos, P., Picaud, S., Mangos, M., Keates, T., Lambert, J.P., Barsyte-Lovejoy, D., et al. Histone recognition and large-scale structural analysis of the human bromodomain family. Cell 149 (2012), 214–231.
2. [2] Smith, S.G., Zhou, M.M., The bromodomain: a new target in emerging epigenetic medicine. ACS Chem Biol 11 (2016), 598–608.
3. [3] Yu, L., Yu, L., Wang, Z., Zhang, Z., Ren, X., Lu, X., Ding, K., et al. Small-molecule BET inhibitors in clinical and preclinical development and their therapeutic potential. Curr Top Med Chem 15 (2015), 776–794.
4. [4] Arrowsmith, C.H., Audia, J.E., Austin, C., Baell, J., Bennett, J., Blagg, J., et al. The promise and peril of chemical probes. Nat Chem Biol 11 (2015), 536–541.
5. [5] Frye, S.V., The art of the chemical probe. Nat Chem Biol 6 (2010), 159–161.
6. [6] Chaidos, A., Caputo, V., Karadimitris, A., Inhibition of bromodomain and extra-terminal proteins (BET) as a potential therapeutic approach in haematological malignancies: emerging preclinical and clinical evidence. Ther Adv Hematol 6 (2015), 128–141.
7. [7] Zhang, G., Smith, S.G., Zhou, M.M., Discovery of chemical inhibitors of human bromodomains. Chem Rev 115 (2015), 11625–11668.
8. [8] Romero, F.A., Taylor, A.M., Crawford, T.D., Tsui, V., Cote, A., Magnuson, S., Disrupting acetyl-lysine recognition: progress in the development of bromodomain inhibitors. J Med Chem 59 (2016), 1271–1298.
9. [9] Theodoulou, N.H., Tomkinson, N.C., Prinjha, R.K., Humphreys, P.G., Progress in the development of non-BET bromodomain chemical probes. ChemMedChem 11 (2016), 477–487.
10. [10] Ullah, M., Pelletier, N., Xiao, L., Zhao, S.P., Wang, K., Degerny, C., et al. Molecular architecture of quartet MOZ/MORF histone acetyltransferase complexes. Mol Cell Biol 28 (2008), 6828–6843.
11. [11] Carlson, S., Glass, K.C., The MOZ histone acetyltransferase in epigenetic signaling and disease. J Cell Physiol 229 (2014), 1571–1574.
12. [12] Yan, K., You, L., Degerny, C., Ghorbani, M., Liu, X., Chen, L., et al. The chromatin regulator BRPF3 preferentially activates the HBO1 acetyltransferase but is dispensable for mouse development and survival. J Biol Chem 291 (2016), 2647–2663.
13. [13] Yang, X.J., MOZ and MORF acetyltransferases: molecular interaction, animal development and human disease. Biochim Biophys Acta 1853 (2015), 1818–1826.
14. [14] Tsai, W.W., Wang, Z., Yiu, T.T., Akdemir, K.C., Xia, W., Winter, S., et al. TRIM24 links a non-canonical histone signature to breast cancer. Nature 468 (2010), 927–932.
15. [15] Allton, K., Jain, A.K., Herz, H.M., Tsai, W.W., Jung, S.Y., Qin, J., et al. Trim24 targets endogenous p53 for degradation. Proc Natl Acad Sci U S A 106 (2009), 11612–11616.
16. [16] Jain, A.K., Allton, K., Duncan, A.D., Barton, M.C., TRIM24 is a p53-induced E3-ubiquitin ligase that undergoes ATM-mediated phosphorylation and autodegradation during DNA damage. Mol Cell Biol 34 (2014), 2695–2709.
17. [17] Khetchoumian, K., Teletin, M., Tisserand, J., Herquel, B., Ouararhni, K., Losson, R., Trim24 (Tif1 alpha): an essential ‘brake’ for retinoic acid-induced transcription to prevent liver cancer. Cell Cycle 7 (2008), 3647–3652.
18. [18] Hatakeyama, S., TRIM proteins and cancer. Nat Rev Cancer 11 (2011), 792–804.
19. [19] Cui, Z., Cao, W., Li, J., Song, X., Mao, L., Chen, W., TRIM24 overexpression is common in locally advanced head and neck squamous cell carcinoma and correlates with aggressive malignant phenotypes. PLoS ONE, 8, 2013, e63887.
20. [20] Liu, X., Huang, Y., Yang, D., Li, X., Liang, J., Lin, L., et al. Overexpression of TRIM24 is associated with the onset and progress of human hepatocellular carcinoma. PLOS ONE, 9, 2014, e85462.
21. [21] Xue, D., Zhang, X., Zhang, X., Liu, J., Li, N., Liu, C., et al. Clinical significance and biological roles of TRIM24 in human bladder carcinoma. Tumour Biol 36 (2015), 6849–6855.
22. [22] Zhang, L.H., Yin, A.A., Cheng, J.X., Huang, H.Y., Li, X.M., Zhang, Y.Q., et al. TRIM24 promotes glioma progression and enhances chemoresistance through activation of the PI3K/Akt signaling pathway. Oncogene 34 (2015), 600–610.
23. [23] Miao, Z.F., Wang, Z.N., Zhao, T.T., Xu, Y.Y., Wu, J.H., Liu, X.Y., et al. TRIM24 is upregulated in human gastric cancer and promotes gastric cancer cell growth and chemoresistance. Virchows Arch 466 (2015), 525–532.
24. [24] Fish, P.V., Filippakopoulos, P., Bish, G., Brennan, P.E., Bunnage, M.E., Cook, A.S., et al. Identification of a chemical probe for bromo and extra C-terminal bromodomain inhibition through optimization of a fragment-derived hit. J Med Chem 55 (2012), 9831–9837.
25. [25] Ferguson, F.M., Fedorov, O., Chaikuad, A., Philpott, M., Muniz, J.R., Felletar, I., et al. Targeting low-druggability bromodomains: fragment based screening and inhibitor design against the BAZ2B bromodomain. J Med Chem 56 (2013), 10183–10187.
26. [26] Demont, E.H., Bamborough, P., Chung, C.W., Craggs, P.D., Fallon, D., Gordon, L.J., et al. 1,3-Dimethyl benzimidazolones are potent, selective inhibitors of the BRPF1 bromodomain. ACS Med Chem Lett 5 (2014), 1190–1195.
27. [27] Harner, M.J., Chauder, B.A., Phan, J., Fesik, S.W., Fragment-based screening of the bromodomain of ATAD2. J Med Chem 57 (2014), 9687–9692.
28. [28] Zhao, H., Gartenmann, L., Dong, J., Spiliotopoulos, D., Caflisch, A., Discovery of BRD4 bromodomain inhibitors by fragment-based high-throughput docking. Bioorg Med Chem Lett 24 (2014), 2493–2496.
29. [29] Clark, P.G., Vieira, L.C., Tallant, C., Fedorov, O., Singleton, D.C., Rogers, C.M., et al. LP99: discovery and synthesis of the first selective BRD7/9 bromodomain inhibitor. Angew Chem Int Ed Engl 54 (2015), 6217–6221.
30. [30] Demont, E.H., Chung, C.W., Furze, R.C., Grandi, P., Michon, A.M., Wellaway, C., et al. Fragment-based discovery of low-micromolar ATAD2 bromodomain inhibitors. J Med Chem 58 (2015), 5649–5673.
31. [31] Unzue, A., Xu, M., Dong, J., Wiedmer, L., Spiliotopoulos, D., Caflisch, A., et al. Fragment-based design of selective nanomolar ligands of the CREBBP bromodomain. J Med Chem 59 (2016), 1350–1356.
32. [32] Chaikuad, A., Lang, S., Brennan, P.E., Temperini, C., Fedorov, O., Hollander, J., et al. Structure-based identification of inhibitory fragments targeting the p300/CBP-associated factor bromodomain. J Med Chem 59 (2016), 1648–1653.
33. [33] Philpott, M., Rogers, C.M., Yapp, C., Wells, C., Lambert, J.P., Strain-Damerell, C., et al. Assessing cellular efficacy of bromodomain inhibitors using fluorescence recovery after photobleaching. Epigenet Chromatin, 7, 2014, 14.
34. [34] Zhan, Y., Kost-Alimova, M., Shi, X., Leo, E., Bardenhagen, J.P., Shepard, H.E., et al. Development of novel cellular histone-binding and chromatin-displacement assays for bromodomain drug discovery. Epigenet Chromatin, 8, 2015, 37.
35. [35] Machleidt, T., Woodroofe, C.C., Schwinn, M.K., Méndez, J., Robers, M.B., Zimmerman, K., et al. NanoBRET – a novel BRET platform for the analysis of protein–protein interactions. ACS Chem Biol 10 (2015), 1797–1804.
36. [36] Roberts, J.M., Bradner, J.E., A bead-based proximity assay for BRD4 ligand discovery. Curr Protoc Chem Biol 7 (2015), 263–278.
37. [37] Vangamudi, B., Paul, T.A., Shah, P.K., Kost-Alimova, M., Nottebaum, L., Shi, X., et al. The SMARCA2/4 ATPase domain surpasses the bromodomain as a drug target in SWI/SNF-mutant cancers: insights from cDNA rescue and PFI-3 inhibitor studies. Cancer Res 75 (2015), 3865–3878.
38. [38] Hopkins, A.L., Keseru, G.M., Leeson, P.D., Rees, D.C., Reynolds, C.H., The role of ligand efficiency metrics in drug discovery. Nat Rev Drug Discov 13 (2014), 105–121.
39. ® Technology Platform. http://www.discoverx.com/technologies-platforms/competitive-binding-technology/bromoscan-technology-platform.
40. [40] Bamborough, P., Barnett, H.A., Becher, I., Bird, M.J., Chung, C.W., Craggs, P.D., et al. GSK6853, a chemical probe for inhibition of the BRPF1 bromodomain. ACS Med Chem Lett, 2016, 10.1021/acsmedchemlett.6b00092.
41. [41] Bamborough P, Chung CW, Legall A, Sheppard RJ (2016) 1,3-Dimethylbenzimidazolone derivative as an inhibitor of the BRPF1 bromodomain. WO2016062737, GlaxoSmithKline.
42. [42] Brown, P.J., Müller, S., Open access chemical probes for epigenetic targets. Future Med Chem 7 (2015), 1901–1917.
43. [43] PFI-4 A chemical probe for BRPF1B. http://www.thesgc.org/chemical-probes/PFI-4.
44. [44] OF-1 A chemical probe for BRPF bromodomains. http://www.thesgc.org/chemical-probes/OF-1.
45. [45] Fish PV, Igoe N, Bayle ED. (2016). Quinolines as inhibitors of class IV bromodomain proteins. WO2016034512, UCL Business PLC.
46. [46] NI-57 A chemical probe for BRPF bromodomains. http://www.thesgc.org/chemical-probes/NI-57.
47. [47] Bennett, J., Fedorov, O., Tallant, C., Monteiro, O., Meier, J., Gamble, V., et al. Discovery of a chemical tool inhibitor targeting the bromodomains of TRIM24 and BRPF. J Med Chem 59 (2016), 1642–1647.
48. [48] Palmer, W.S., Poncet-Montange, G., Liu, G., Petrocchi, A., Reyna, N., Subramanian, G., et al. Structure-guided design of IACS-9571, a selective high-affinity dual TRIM24-BRPF1 bromodomain inhibitor. J Med Chem 59 (2016), 1440–1454.
49. [49] Palmer WS, Jones P, Liu G, Petrocchi A, Reyna N, Subramanian G, et al. (2016) Bromodomain inhibitors for treating disease. WO2016033416, University of Texas System, USA.