Correction to: Discovery of pyrazolo[1,5-a]pyrimidine b-cell lymphoma 6 (BCL6) binders and optimization to high affinity macrocyclic inhibitors (Journal of Medicinal Chemistry (2017) 60 (4386-4402): DOI: 10.1021/acs.jmedchem.7b00359);Discovery of Pyrazolo[1,5-a]pyrimidine B-Cell Lymphoma 6 (BCL6) Binders and Optimization to High Affinity Macrocyclic Inhibitors

Journal of Medicinal Chemistry

Volumn 60, Issue 10, 2017, Pages 4386-4402

  McCoull, William ^a   Abrams, Roman D ^a   Anderson, Erica ^a   Blades, Kevin ^a,c   Barton, Peter ^a   Box, Matthew ^a,c   Burgess, Jonathan ^a   Byth, Kate ^a   Cao, Qing ^a,d   Chuaqui, Claudio ^a   Carbajo, Rodrigo J ^a   Cheung, Tony ^a   Code, Erin ^a   Ferguson, Andrew D ^a   Fillery, Shaun ^a   Fuller, Nathan O ^a,f   Gangl, Eric ^a   Gao, Ning ^a   Grist, Matthew ^a,g   Hargreaves, David ^a   Howard, Martin R ^a   Hu, Jun ^a,e   Kemmitt, Paul D ^a   Nelson, Jennifer E ^a   O’Connell, Nichole ^a,h   Prince, D Bryan ^a   Raubo, Piotr ^a   Rawlins, Philip B ^a   Robb, Graeme R ^a   Shi, Junjie ^b   Waring, Michael J ^a,i   Whittaker, David ^a   Wylot, Marta ^a   Zhu, Xiahui ^a   more..

^a ASTRAZENECA   (United Kingdom)

^b Pharmaron Beijing Co Ltd   (China)

^c REDX PHARMA   (United Kingdom)

^d Pharmaceuticals   (United States)

^e Macclesfield ^*  (United States)

^f Life Science Suites   (United States)

^g Medtrade Products Ltd   (United Kingdom)

^h Nurix Inc   (United States)

ⁱ NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CASEIN KINASE II; LIGAND; MACROCYCLIC COMPOUND; NUCLEAR RECEPTOR COREPRESSOR; PROTEIN BCL 6; PYRAZOLO[1,5 A]PYRIMIDINE DERIVATIVE; BCL6 PROTEIN, HUMAN; PYRAZOLE DERIVATIVE; PYRAZOLO(3,4-B)PYRIDINE; PYRIDINE DERIVATIVE;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BINDING AFFINITY; CONFORMATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; HUMAN; HUMAN CELL; LARGE CELL LYMPHOMA; LIPOPHILICITY; MULTIPLE MYELOMA CELL LINE; PROTEIN INTERACTION; SCIENCE; ANTAGONISTS AND INHIBITORS; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECTS; LYMPHOMA, LARGE B-CELL, DIFFUSE; METABOLISM; MOLECULAR DOCKING; PROTEIN PROTEIN INTERACTION; TUMOR CELL LINE;

CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; HUMANS; LYMPHOMA, LARGE B-CELL, DIFFUSE; MOLECULAR DOCKING SIMULATION; PROTEIN INTERACTION MAPS; PROTO-ONCOGENE PROTEINS C-BCL-6; PYRAZOLES; PYRIDINES;

EID: 85019666730     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.7b00962     Document Type: Erratum

References (25)

1. Basso, K.; Dalla-Favera, R. Roles of BCL6 in normal and transformed germinal center B cells Immunol. Rev. 2012, 247, 172-183 10.1111/j.1600-065X.2012.01112.x
2. Cattoretti, G.; Pasqualucci, L.; Ballon, G.; Tam, W.; Nandula, S. V.; Shen, Q.; Mo, T.; Murty, V. V.; Dalla-Favera, R. Deregulated BCL6 expression recapitulates the pathogenesis of human diffuse large B cell lymphomas in mice Cancer Cell 2005, 7, 445-455 10.1016/j.ccr.2005.03.037
3. Ranuncolo, S. M.; Polo, J. M.; Dierov, J.; Singer, M.; Kuo, T.; Greally, J.; Green, R.; Carroll, M.; Melnick, A. Bcl-6 mediates the germinal center B cell phenotype and lymphomagenesis through transcriptional repression of the DNA-damage sensor ATR Nat. Immunol. 2007, 8, 705-714 10.1038/ni1478
4. Huang, C.; Hatzi, K.; Melnick, A. Lineage-specific functions of Bcl-6 in immunity and inflammation are mediated by distinct biochemical mechanisms Nat. Immunol. 2013, 14, 380-388 10.1038/ni.2543
5. Cardenas, M. G.; Yu, W.; Beguelin, W.; Teater, M. R.; Geng, H.; Goldstein, R. L.; Oswald, E.; Hatzi, K.; Yang, S. N.; Cohen, J.; Shaknovich, R.; Vanommeslaeghe, K.; Cheng, H.; Liang, D.; Cho, H. J.; Abbott, J.; Tam, W.; Du, W.; Leonard, J. P.; Elemento, O.; Cerchietti, L.; Cierpicki, T.; Xue, F.; MacKerell, A. D., Jr.; Melnick, A. M. Rationally designed BCL6 inhibitors target activated B cell diffuse large B cell lymphoma J. Clin. Invest. 2016, 126, 3351-3362 10.1172/JCI85795
6. Cerchietti, L. C.; Yang, S. N.; Shaknovich, R.; Hatzi, K.; Polo, J. M.; Chadburn, A.; Dowdy, S. F.; Melnick, A. A peptomimetic inhibitor of BCL6 with potent antilymphoma effects in vitro and in vivo Blood 2009, 113, 3397-3405 10.1182/blood-2008-07-168773
7. Sakamoto, K.; Sogabe, S.; Kamada, Y.; Sakai, N.; Asano, K.; Yoshimatsu, M.; Ida, K.; Imaeda, Y.; Sakamoto, J.-i. Discovery of high-affinity BCL6-binding peptide and its structure-activity relationship Biochem. Biophys. Res. Commun. 2017, 482, 310-316 10.1016/j.bbrc.2016.11.060
8. Cardenas, M. G.; Oswald, E.; Yu, W.; Xue, F.; MacKerell, A. D., Jr.; Melnick, A. M. The expanding role of the BCL6 oncoprotein as a cancer therapeutic target Clin. Cancer Res. 2017, 23, 885-893 10.1158/1078-0432.CCR-16-2071
9. Huynh, K. D.; Bardwell, V. J. The BCL-6 POZ domain and other POZ domains interact with the co-repressors N-CoR and SMRT Oncogene 1998, 17, 2473-2484 10.1038/sj.onc.1202197
10. Huynh, K. D.; Fischle, W.; Verdin, E.; Bardwell, V. J. BCoR, a novel corepressor involved in BCL-6 repression Genes Dev. 2000, 14, 1810-1823 10.1101/gad.14.14.1810
11. Scott, D. E.; Bayly, A. R.; Abell, C.; Skidmore, J. Small molecules, big targets: drug discovery faces the protein-protein interaction challenge Nat. Rev. Drug Discovery 2016, 15, 533-550 10.1038/nrd.2016.29
12. Ghetu, A. F.; Corcoran, C. M.; Cerchietti, L.; Bardwell, V. J.; Melnick, A.; Prive, G. G. Structure of a BCOR corepressor peptide in complex with the BCL6 BTB domain dimer Mol. Cell 2008, 29, 384-391 10.1016/j.molcel.2007.12.026
13. Ahmad, K. F.; Melnick, A.; Lax, S.; Bouchard, D.; Liu, J.; Kiang, C. L.; Mayer, S.; Takahashi, S.; Licht, J. D.; Prive, G. G. Mechanism of SMRT corepressor recruitment by the BCL6 BTB domain Mol. Cell 2003, 12, 1551-1564 10.1016/S1097-2765(03)00454-4
14. Kuntz, I. D.; Chen, K.; Sharp, K. A.; Kollman, P. A. The maximal affinity of ligands Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 9997-10002 10.1073/pnas.96.18.9997
15. Leeson, P. D.; Springthorpe, B. The influence of drug-like concepts on decision-making in medicinal chemistry Nat. Rev. Drug Discovery 2007, 6, 881-890 10.1038/nrd2445
16. Kovalenko, A.; Hirata, F. Potentials of mean force of simple ions in ambient aqueous solution. I. Three-dimensional reference interaction site model approach J. Chem. Phys. 2000, 112, 10391-10402 10.1063/1.481676
17. Butts, C. P.; Jones, C. R.; Towers, E. C.; Flynn, J. L.; Appleby, L.; Barron, N. J. Interproton distance determinations by NOE--surprising accuracy and precision in a rigid organic molecule Org. Biomol. Chem. 2011, 9, 177-184 10.1039/C0OB00479K
18. Troche-Pesqueira, E.; Anklin, C.; Gil, R. R.; Navarro-Vázquez, A. Computer-assisted 3D structure elucidation of natural products using residual dipolar couplings Angew. Chem., Int. Ed. 2017, 56, 3660-3664 10.1002/anie.201612454
19. Bonnet, P.; Agrafiotis, D. K.; Zhu, F.; Martin, E. Conformational analysis of macrocycles: finding what common search methods miss J. Chem. Inf. Model. 2009, 49, 2242-2259 10.1021/ci900238a
20. Watts, K. S.; Dalal, P.; Tebben, A. J.; Cheney, D. L.; Shelley, J. C. Macrocycle conformational sampling with MacroModel J. Chem. Inf. Model. 2014, 54, 2680-2696 10.1021/ci5001696
21. Copeland, R. A.; Pompliano, D. L.; Meek, T. D. Drug-target residence time and its implications for lead optimization Nat. Rev. Drug Discovery 2006, 5, 730-739 10.1038/nrd2082
22. Dowling, J. E.; Alimzhanov, M.; Bao, L.; Chuaqui, C.; Denz, C. R.; Jenkins, E.; Larsen, N. A.; Lyne, P. D.; Pontz, T.; Ye, Q.; Holdgate, G. A.; Snow, L.; O’Connell, N.; Ferguson, A. D. Potent and selective CK2 kinase inhibitors with effects on Wnt pathway signaling in vivo ACS Med. Chem. Lett. 2016, 7, 300-305 10.1021/acsmedchemlett.5b00452
23. Bowes, J.; Brown, A. J.; Hamon, J.; Jarolimek, W.; Sridhar, A.; Waldron, G.; Whitebread, S. Reducing safety-related drug attrition: the use of in vitro pharmacological profiling Nat. Rev. Drug Discovery 2012, 11, 909-922 10.1038/nrd3845
24. Hideshima, T.; Mitsiades, C.; Ikeda, H.; Chauhan, D.; Raje, N.; Gorgun, G.; Hideshima, H.; Munshi, N. C.; Richardson, P. G.; Carrasco, D. R.; Anderson, K. C. A proto-oncogene BCL6 is up-regulated in the bone marrow microenvironment in multiple myeloma cells Blood 2010, 115, 3772-3775 10.1182/blood-2010-02-270082
25. Pervushin, K.; Riek, R.; Wider, G.; Wüthrich, K. Attenuated T2 relaxation by mutual cancellation of dipole-dipole coupling and chemical shift anisotropy indicates an avenue to NMR structures of very large biological macromolecules in solution Proc. Natl. Acad. Sci. U. S. A. 1997, 94, 12366-12371 10.1073/pnas.94.23.12366