SAR by interligand nuclear overhauser effects (ILOEs) based discovery of acylsulfonamide compounds active against Bcl-xL and Mcl-1

Journal of Medicinal Chemistry

Volumn 54, Issue 17, 2011, Pages 6000-6013

  Rega, Michele F ^a   Wu, Bainan ^a   Wei, Jun ^a   Zhang, Ziming ^a   Cellitti, Jason F ^a   Pellecchia, Maurizio ^a  

^a BURNHAM INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLSULFONAMIDE COMPOUND; ANTINEOPLASTIC AGENT; BCL2 RELATED PROTEIN A1; PROTEIN BCL 2; PROTEIN BCL W; PROTEIN BCL XL; PROTEIN MCL 1; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; IN VITRO STUDY; LIGAND BINDING; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; STRUCTURE ACTIVITY RELATION;

ACYLATION; BCL-X PROTEIN; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; PROTO-ONCOGENE PROTEINS C-BCL-2; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 80052384557     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm200826s     Document Type: Article

References (36)

1. Shuker, S. B.; Hajduk, P. J.; Meadows, R. P.; Fesik, S. W. Discovering high-affinity ligands for proteins: SAR by NMR Science 1996, 274, 1531-1534 (Pubitemid 26403929)
2. Hajduk, P. J.; Gerfin, T.; Boehlen, J. M.; Haberli, M.; Marek, D.; Fesik, S. W. High-throughput nuclear magnetic resonance-based screening J. Med. Chem. 1999, 42, 2315-2317 (Pubitemid 29305164)
3. Whitty, A.; Kumaravel, G. Between a rock and a hard place? Nature Chem. Biol. 2006, 2, 112-118 (Pubitemid 44323856)
4. Pellecchia, M. Solution nuclear magnetic resonance spectroscopy techniques for probing intermolecular interactions Chem. Biol. 2005, 12, 961-971 (Pubitemid 41338806)
5. Pellecchia, M.; Becattini, B.; Crowell, K. J.; Fattorusso, R.; Forino, M.; Fragai, M.; Jung, D.; Mustelin, T.; Tautz, L. NMR-based techniques in the hit identification and optimization processes Expert Opin. Ther. Targets 2004, 8, 597-611 (Pubitemid 40028369)
6. Petros, A. M.; Dinges, J.; Augeri, D. J.; Baumeister, S. A.; Betebenner, D. A.; Bures, M. G.; Elmore, S. W.; Hajduk, P. J.; Joseph, M. K.; Landis, S. K.; Nettesheim, D. G.; Rosenberg, S. H.; Shen, W.; Thomas, S.; Wang, X.; Zanze, I.; Zhang, H.; Fesik, S. W. Discovery of a potent inhibitor of the antiapoptotic protein Bcl-xL from NMR and parallel synthesis J. Med. Chem. 2006, 49, 656-663 (Pubitemid 43157495)
7. Oltersdorf, T.; Elmore, S. W.; Shoemaker, A. R.; Armstrong, R. C.; Augeri, D. J.; Belli, B. A.; Bruncko, M.; Deckwerth, T. L.; Dinges, J.; Hajduk, P. J.; Joseph, M. K.; Kitada, S.; Korsmeyer, S. J.; Kunzer, A. R.; Letai, A.; Li, C.; Mitten, M. J.; Nettesheim, D. G.; Ng, S.; Nimmer, P. M.; O'Connor, J. M.; Oleksijew, A.; Petros, A. M.; Reed, J. C.; Shen, W.; Tahir, S. K.; Thompson, C. B.; Tomaselli, K. J.; Wang, B.; Wendt, M. D.; Zhang, H.; Fesik, S. W.; Rosenberg, S. H. An inhibitor of Bcl-2 family proteins induces regression of solid tumours Nature 2005, 435, 677-681 (Pubitemid 40825512)
8. Konopleva, M.; Contractor, R.; Tsao, T.; Samudio, I.; Ruvolo, P. P.; Kitada, S.; Deng, X.; Zhai, D.; Shi, Y. X.; Sneed, T.; Verhaegen, M.; Soengas, M.; Ruvolo, V. R.; McQueen, T.; Schober, W. D.; Watt, J. C.; Jiffar, T.; Ling, X.; Marini, F. C.; Harris, D.; Dietrich, M.; Estrov, Z.; McCubrey, J.; May, W. S.; Reed, J. C.; Andreeff, M. Mechanisms of apoptosis sensitivity and resistance to the BH3 mimetic ABT-737 in acute myeloid leukemia Cancer Cell 2006, 10, 375-388 (Pubitemid 44693472)
9. van Delft, M. F.; Wei, A. H.; Mason, K. D.; Vandenberg, C. J.; Chen, L.; Czabotar, P. E.; Willis, S. N.; Scott, C. L.; Day, C. L.; Cory, S.; Adams, J. M.; Roberts, A. W.; Huang, D. C. The BH3 mimetic ABT-737 targets selective Bcl-2 proteins and efficiently induces apoptosis via Bak/Bax if Mcl-1 is neutralized Cancer Cell 2006, 10, 389-399 (Pubitemid 44711953)
10. Del Gaizo Moore, V.; Brown, J. R.; Certo, M.; Love, T. M.; Novina, C. D.; Letai, A. Chronic lymphocytic leukemia requires BCL2 to sequester prodeath BIM, explaining sensitivity to BCL2 antagonist ABT-737 J. Clin. Invest. 2007, 117, 112-121 (Pubitemid 46048458)
11. Dash, R.; Azab, B.; Quinn, B. A.; Shen, X.; Wang, X. Y.; Das, S. K.; Rahmani, M.; Wei, J.; Hedvat, M.; Dent, P.; Dmitriev, I. P.; Curiel, D. T.; Grant, S.; Wu, B.; Stebbins, J. L.; Pellecchia, M.; Reed, J. C.; Sarkar, D.; Fisher, P. B. Apogossypol derivative BI-97C1 (Sabutoclax) targeting Mcl-1 sensitizes prostate cancer cells to mda-7/IL-24-mediated toxicity Proc. Natl. Acad. Sci. U.S.A 2011, 108, 8785-8790
12. Becattini, B.; Pellecchia, M. SAR by ILOEs: An NMR-Based Approach to Reverse Chemical Genetics Chemistry 2006, 12, 2658-2662
13. Becattini, B.; Sareth, S.; Zhai, D.; Crowell, K. J.; Leone, M.; Reed, J. C.; Pellecchia, M. Targeting apoptosis via chemical design: inhibition of bid-induced cell death by small organic molecules Chem. Biol. 2004, 11, 1107-1117 (Pubitemid 39138763)
14. Becattini, B.; Culmsee, C.; Leone, M.; Zhai, D.; Zhang, X.; Crowell, K. J.; Rega, M. F.; Landshamer, S.; Reed, J. C.; Plesnila, N.; Pellecchia, M. Structure-activity relationships by interligand NOE-based design and synthesis of antiapoptotic compounds targeting Bid Proc. Natl. Acad. Sci. U.S.A 2006, 103, 12602-12606 (Pubitemid 44267305)
15. Fejzo, J.; Lepre, C. A.; Peng, J. W.; Bemis, G. W.; Ajay; Murcko, M. A.; Moore, J. M. The SHAPES strategy: an NMR-based approach for lead generation in drug discovery Chem. Biol. 1999, 6, 755-769 (Pubitemid 29485537)
16. Ni, F. Recent developments in transferred NOEs methods Prog. Nucl. Magn. Reson. Spectrosc. 1994, 26, 517-606 (Pubitemid 124003834)
17. Mayer, M.; Meyer, B. Mapping the active site of angiotensin-converting enzyme by transferred NOE spectroscopy J. Med. Chem. 2000, 43, 2093-2099 (Pubitemid 30354534)
18. Kumar, A.; Ernst, R. R.; Wuthrich, K. A two-dimensional nuclear Overhauser enhancement (2D NOE) experiment for the elucidation of complete proton-proton cross-relaxation networks in biological macromolecules Biochem. Biophys. Res. Commun. 1980, 95, 1-6
19. Jahnke, W.; Florsheimer, A.; Blommers, M. J.; Paris, C. G.; Heim, J.; Nalin, C. M.; Perez, L. B. Second-site NMR screening and linker design Curr. Top. Med. Chem. 2003, 3, 69-80
20. Li, D.; DeRose, E. F.; London, R. E. The interligand Overhauser effect: a powerful new NMR approach for mapping structural relationships of macromolecular ligands J. Biomol. NMR 1999, 15, 71-76 (Pubitemid 29488030)
21. Pellecchia, M.; Meininger, D.; Dong, Q.; Chang, E.; Jack, R.; Sem, D. S. NMR-based structural characterization of large protein-ligand interactions J. Biomol. NMR 2002, 22, 165-173 (Pubitemid 34173235)
22. Zerbe, O. BioNMR in Drug Research; WILEY-VCH: New York, 2003; pp 439-457.
23. Kline, A. SAR by NOE? NMR Newsletter 1997, 13, 472
24. Bemis, G. W.; Murcko, M. A. The properties of known drugs. 1. Molecular frameworks J. Med. Chem. 1996, 39, 2887-2893 (Pubitemid 26251026)
25. Becattini, B.; Pellecchia, M. SAR by ILOEs: an NMR-based approach to reverse chemical genetics Chemistry 2006, 12, 2658-2662
26. Rega, M. F.; Leone, M.; Jung, D.; Cotton, N. J.; Stebbins, J. L.; Pellecchia, M. Structure-based discovery of a new class of Bcl-xL antagonists Bioorg. Chem. 2007, 35, 344-353 (Pubitemid 46990472)
27. Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking J. Mol. Biol. 1997, 267, 727-748 (Pubitemid 27170693)
28. Eldridge, M. D.; Murray, C. W.; Auton, T. R.; Paolini, G. V.; Mee, R. P. Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes J. Comput.-Aided Mol. Des. 1997, 11, 425-445 (Pubitemid 127505895)
29. Placzek, W. J.; Wei, J.; Kitada, S.; Zhai, D.; Reed, J. C.; Pellecchia, M. A survey of the anti-apoptotic Bcl-2 subfamily expression in cancer types provides a platform to predict the efficacy of Bcl-2 antagonists in cancer therapy Cell Death Dis. 2010, 1, e40
30. Wei, J.; Stebbins, J. L.; Kitada, S.; Dash, R.; Placzek, W.; Rega, M. F.; Wu, B.; Cellitti, J.; Zhai, D.; Yang, L.; Dahl, R.; Fisher, P. B.; Reed, J. C.; Pellecchia, M. BI-97C1, an optically pure apogossypol derivative as pan-active inhibitor of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins J. Med. Chem. 2010, 53, 4166-4176
31. Lee, E. F.; Czabotar, P. E.; Smith, B. J.; Deshayes, K.; Zobel, K.; Colman, P. M.; Fairlie, W. D. Crystal structure of ABT-737 complexed with Bcl-xL: implications for selectivity of antagonists of the Bcl-2 family Cell Death Differ. 2007, 14, 1711-1713 (Pubitemid 47278856)
32. Bruncko, M.; Oost, T. K.; Belli, B. A.; Ding, H.; Joseph, M. K.; Kunzer, A.; Martineau, D.; McClellan, W. J.; Mitten, M.; Ng, S. C.; Nimmer, P. M.; Oltersdorf, T.; Park, C. M.; Petros, A. M.; Shoemaker, A. R.; Song, X.; Wang, X.; Wendt, M. D.; Zhang, H.; Fesik, S. W.; Rosenberg, S. H.; Elmore, S. W. Studies leading to potent, dual inhibitors of Bcl-2 and Bcl-xL J. Med. Chem. 2007, 50, 641-662 (Pubitemid 46332978)
33. Czabotar, P. E.; Lee, E. F.; van Delft, M. F.; Day, C. L.; Smith, B. J.; Huang, D. C.; Fairlie, W. D.; Hinds, M. G.; Colman, P. M. Structural insights into the degradation of Mcl-1 induced by BH3 domains Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 6217-6222 (Pubitemid 47186075)
34. Teschner, M.; Henn, C.; Vollhardt, H.; Reiling, S.; Brickmann, J. Texture mapping: a new tool for molecular graphics J. Mol. Graphics 1994, 12, 98-105 (Pubitemid 24219249)
35. Sattler, M.; Liang, H.; Nettesheim, D.; Meadows, R. P.; Harlan, J. E.; Eberstadt, M.; Yoon, H. S.; Shuker, S. B.; Chang, B. S.; Minn, A. J.; Thompson, C. B.; Fesik, S. W. Structure of Bcl-xL-Bak peptide complex: recognition between regulators of apoptosis Science 1997, 275, 983-986 (Pubitemid 27087715)
36. Ramjaun, A. R.; Tomlinson, S.; Eddaoudi, A.; Downward, J. Upregulation of two BH3-only proteins, Bmf and Bim, during TGF beta-induced apoptosis Oncogene 2007, 26, 970-981