Recent advances in the structure-based rational design of TNKSIs

Molecular BioSystems

Volumn 10, Issue 11, 2014, Pages 2783-2799

  Zhan, Peng ^a,b   Song, Yu'Ning ^a   Itoh, Yukihiro ^b   Suzuki, Takayoshi ^b   Liu, Xinyong ^a  

^a SHANDONG UNIVERSITY   (China)

^b KYOTO PREFECTURAL UNIVERSITY OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; TANKYRASE; TNKS PROTEIN, HUMAN; TNKS2 PROTEIN, HUMAN;

ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; DRUG EFFECTS; ENZYME ACTIVE SITE; HUMAN; METABOLISM; SIGNAL TRANSDUCTION;

CATALYTIC DOMAIN; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; MODELS, MOLECULAR; SIGNAL TRANSDUCTION; TANKYRASES;

EID: 84907677397     PISSN: 1742206X     EISSN: 17422051     Source Type: Journal    
DOI: 10.1039/c4mb00385c     Document Type: Review

References (49)

1. J. L. Riffell C. J. Lord A. Ashworth Tankyrase-targeted therapeutics: expanding opportunities in the PARP family Nat. Rev. Drug Discovery 2012 11 923 936
2. S. Vyas P. Chang New PARP targets for cancer therapy Nat. Rev. Cancer 2014 14 502 509
3. V. Schreiber F. Dantzer J. C. Ame G. de Murcia Poly(ADP-ribose): novel functions for an old molecule Nat. Rev. Mol. Cell Biol. 2006 7 517 528
4. A. M. Busch K. C. Johnson R. V. Stan A. Sanglikar Y. Ahmed E. Dmitrovsky S. J. Freemantle Evidence for tankyrases as antineoplastic targets in lung cancer BMC Cancer 2013 13 211
5. L. Lehtiö N. W. Chi S. Krauss Tankyrases as drug targets FEBS J. 2013 280 3576 3593
6. P. Liscio E. Camaioni A. Carotti R. Pellicciari A. Macchiarulo From polypharmacology to target specificity: the case of PARP inhibitors Curr. Top. Med. Chem. 2013 13 2939 2954
7. B. Chen M. E. Dodge W. Tang J. Lu Z. Ma C. W. Fan S. Wei W. Hao J. Kilgore N. S. Williams M. G. Roth J. F. Amatruda C. Chen L. Lum Small molecule-mediated disruption of Wnt-dependent signaling in tissue regeneration and cancer Nat. Chem. Biol. 2009 5 100 107
8. J. Lu Z. Ma J. C. Hsieh C. W. Fan B. Chen J. C. Longgood N. S. Williams J. F. Amatruda L. Lum C. Chen Structure-activity relationship studies of small-molecule inhibitors of Wnt response Bioorg. Med. Chem. Lett. 2009 19 3825 3827
9. S. M. Huang Y. M. Mishina S. Liu A. Cheung F. Stegmeier G. A. Michaud O. Charlat E. Wiellette Y. Zhang S. Wiessner M. Hild X. Shi C. J. Wilson C. Mickanin V. Myer A. Fazal R. Tomlinson F. Serluca W. Shao H. Cheng M. Shultz C. Rau M. Schirle J. Schlegl S. Ghidelli S. Fawell C. Lu D. Curtis M. W. Kirschner C. Lengauer P. M. Finan J. A. Tallarico T. Bouwmeester J. A. Porter A. Bauer F. Cong Tankyrase inhibition stabilizes axin and antagonizes Wnt signalling Nature 2009 461 614 620
10. E. R. Fearon PARsing the phrase "all in for Axin"-Wnt pathway targets in cancer Cancer Cell 2009 16 366 368
11. C. Liu X. He Destruction of a destructor: a new avenue for cancer therapeutics targeting the Wnt pathway J. Mol. Cell Biol. 2010 2 70 73
12. X. H. Tian W. J. Hou Y. Fang J. Fan H. Tong S. L. Bai Q. Chen H. Xu Y. Li XAV939, a tankyrase 1 inhibitor, promotes cell apoptosis in neuroblastoma cell lines by inhibiting Wnt/β-catenin signaling pathway J. Exp. Clin. Cancer Res. 2013 32 100
13. J. Waaler O. Machon J. P. von Kries S. R. Wilson E. Lundenes D. Wedlich D. Gradl J. E. Paulsen O. Machonova J. L. Dembinski H. Dinh S. Krauss Novel synthetic antagonists of canonical Wnt signaling inhibit colorectal cancer cell growth Cancer Res. 2011 71 197 205
14. E. Wessel Stratford J. Daffinrud E. Munthe R. Castro J. Waaler S. Krauss O. Myklebost The tankyrase-specific inhibitor JW74 affects cell cycle progression and induces apoptosis and differentiation in osteosarcoma cell lines Cancer Med. 2014 3 36 46
15. M. D. Shultz C. A. Kirby T. Stams D. N. Chin J. Blank O. Charlat H. Cheng A. Cheung F. Cong Y. Feng P. D. Fortin T. Hood V. Tyagi M. Xu B. Zhang W. Shao [1,2,4]triazol-3-ylsulfanylmethyl-3-phenyl-[1,2,4]oxadiazoles: antagonists of the Wnt pathway that inhibit tankyrases 1 and 2 via novel adenosine pocket binding J. Med. Chem. 2012 55 1127 1136
16. A. Voronkov D. D. Holsworth J. Waaler S. R. Wilson B. Ekblad H. Perdreau-Dahl H. Dinh G. Drewes C. Hopf J. P. Morth S. Krauss Structural basis and SAR for G007-LK, a lead stage 1,2,4-triazole based specific tankyrase 1/2 inhibitor J. Med. Chem. 2013 56 3012 3023
17. T. Lau E. Chan M. Callow J. Waaler J. Boggs R. A. Blake S. Magnuson A. Sambrone M. Schutten R. Firestein O. Machon V. Korinek E. Choo D. Diaz M. Merchant P. Polakis D. D. Holsworth S. Krauss M. Costa A novel tankyrase small-molecule inhibitor suppresses APC mutation-driven colorectal tumor growth Cancer Res. 2013 73 3132 3144
18. R. G. James K. C. Davidson K. A. Bosch T. L. Biechele N. C. Robin R. J. Taylor M. B. Major N. D. Camp K. Fowler T. J. Martins R. T. Moon WIKI4, a novel inhibitor of tankyrase and Wnt/β-catenin signaling PLoS One 2012 7 e50457
19. T. Haikarainen H. Venkannagari M. Narwal E. Obaji H. W. Lee Y. Nkizinkiko L. Lehtiö Structural basis and selectivity of tankyrase inhibition by a Wnt signaling inhibitor WIKI4 PLoS One 2013 8 e65404
20. J. Waaler O. Machon L. Tumova H. Dinh V. Korinek S. R. Wilson J. E. Paulsen N. M. Pedersen T. J. Eide O. Machonova D. Gradl A. Voronkov J. P. von Kries S. Krauss A novel tankyrase inhibitor decreases canonical Wnt signaling in colon carcinoma cells and reduces tumor growth in conditional APC mutant mice Cancer Res. 2012 72 2822 2832
21. T. Karlberg N. Markova I. Johansson M. Hammarström P. Schütz J. Weigelt H. Schüler Structural basis for the interaction between tankyrase-2 and a potent Wnt-signaling inhibitor J. Med. Chem. 2010 53 5352 5355
22. C. A. Kirby A. Cheung A. Fazal M. D. Shultz T. Stams Structure of human tankyrase 1 in complex with small-molecule inhibitors PJ34 and XAV939 Acta Crystallogr., Sect. F: Struct. Biol. Cryst. Commun. 2012 68 115 118
23. H. Gunaydin Y. Gu X. Huang Novel binding mode of a potent and selective tankyrase inhibitor PLoS One 2012 7 e33740
24. M. Narwal H. Venkannagari L. Lehtiö Structural basis of selective inhibition of human tankyrases J. Med. Chem. 2012 55 1360 1367
25. T. Haikarainen M. Narwal P. Joensuu L. Lehtiö Evaluation and Structural Basis for the Inhibition of Tankyrases by PARP Inhibitors ACS Med. Chem. Lett. 2013 5 18 22
26. Y. Song P. Zhan X. Li D. Rai E. De Clercq X. Liu Multivalent agents: a novel concept and preliminary practice in Anti-HIV drug discovery Curr. Med. Chem. 2013 20 815 832
27. H. Bregman H. Gunaydin Y. Gu S. Schneider C. Wilson E. F. DiMauro X. Huang Discovery of a class of novel tankyrase inhibitors that bind to both the nicotinamide pocket and the induced pocket J. Med. Chem. 2013 56 1341 1345
28. Z. Hua H. Bregman J. L. Buchanan N. Chakka A. Guzman-Perez H. Gunaydin X. Huang Y. Gu V. Berry J. Liu Y. Teffera L. Huang B. Egge R. Emkey E. L. Mullady S. Schneider P. S. Andrews L. Acquaviva J. Dovey A. Mishra J. Newcomb D. Saffran R. Serafino C. A. Strathdee S. M. Turci M. Stanton C. Wilson E. F. Dimauro Development of novel dual binders as potent, selective and orally bioavailable tankyrase inhibitors J. Med. Chem. 2013 56 10003 10015
29. A. L. Hopkins C. R. Groom A. Alex Ligand efficiency: a useful metric for lead selection Drug Discovery Today 2004 9 430 431
30. C. Abad-Zapatero J. T. Metz Ligand efficiency indices as guideposts for drug discovery Drug Discovery Today 2005 10 464 469
31. C. W. Murray D. A. Erlanson A. L. Hopkins G. M. Keserü P. D. Leeson D. C. Rees C. H. Reynolds N. J. Richmond Validity of ligand efficiency metrics ACS Med. Chem. Lett. 2014 5 616 618
32. P. D. Leeson B. Springthorpe The influence of drug-like concepts on decision making in medicinal chemistry Nat. Rev. Drug Discovery 2007 6 881 890
33. M. D. Shultz A. K. Cheung C. A. Kirby B. Firestone J. Fan Z. Chen D. N. Chin L. Dipietro A. Fazal Y. Feng P. D. Fortin T. Gould B. Lagu H. Lei F. Lenoir D. Majumdar E. Ochala M. G. Palermo L. Pham M. Pu T. Smith T. Stams R. Tomlinson B. B. Touré M. Visser R. Wang N. J. Waters W. Shao Identification of NVP-TNKS656-the use of structure efficiency relationships to generate a highly potent, selective and orally active tankyrase inhibitor J. Med. Chem. 2013 56 6495 6511
34. M. D. Shultz D. Majumdar D. N. Chin P. D. Fortin Y. Feng T. Gould C. A. Kirby T. Stams N. J. Waters W. Shao Structure efficiency relationship of [1,2,4]triazol-3-ylamines as novel nicotinamide isosteres that inhibit tankyrases J. Med. Chem. 2013 56 7049 7059
35. C. Viegas-Junior A. Danuello V. da Silva Bolzani E. J. Barreiro C. A. Fraga Molecular hybridization: a useful tool in the design of new drug prototypes Curr. Med. Chem. 2007 14 1829 1852
36. L. H. Jones G. Allan O. Barba C. Burt R. Corbau T. Dupont T. Knöchel S. Irving D. S. Middleton C. E. Mowbray M. Perros H. Ringrose N. A. Swain R. Webster M. Westby C. Phillips Novel indazole non-nucleoside reverse transcriptase inhibitors using molecular hybridization based on crystallographic overlays J. Med. Chem. 2009 52 1219 1223
37. H. Bregman N. Chakka A. Guzman-Perez H. Gunaydin Y. Gu X. Huang V. Berry J. Liu Y. Teffera L. Huang B. Egge E. L. Mullady S. Schneider P. S. Andrews A. Mishra J. Newcomb R. Serafino C. A. Strathdee S. M. Turci C. Wilson E. F. DiMauro Discovery of novel, induced-pocket binding oxazolidinones as potent, selective and orally bioavailable tankyrase inhibitors J. Med. Chem. 2013 56 4320 4342
38. H. Huang A. Guzman-Perez L. Acquaviva V. Berry H. Bregman J. Dovey H. Gunaydin X. Huang L. Huang D. Saffran R. Serafino S. Schneider C. Wilson E. F. DiMauro Structure-based design of 2-aminopyridine oxazolidinones as potent and selective tankyrase inhibitors ACS Med. Chem. Lett. 2013 4 1218 1223
39. M. J. Hartshorn C. W. Murray A. Cleasby M. Frederickson I. J. Tickle H. Jhoti Fragment-based lead discovery using X-ray crystallography J. Med. Chem. 2005 48 403 413
40. E. A. Larsson A. Jansson F. M. Ng S. W. Then R. Panicker B. Liu K. Sangthongpitag V. Pendharkar S. J. Tai J. Hill C. Dan S. Y. Ho W. W. Cheong A. Poulsen S. Blanchard G. R. Lin J. Alam T. H. Keller P. Nordlund Fragment-based ligand design of novel potent inhibitors of tankyrases J. Med. Chem. 2013 56 4497 4508
41. G. A. Patani E. J. LaVoie Bioisosterism: A Rational Approach in Drug Design Chem. Rev. 1996 96 3147 3176
42. A. Nathubhai P. J. Wood M. D. Lloyd A. S. Thompson M. D. Threadgill Design and Discovery of 2-arylquinazolin-4-ones as potent and selective inhibitors of tankyrases ACS Med. Chem. Lett. 2013 4 1173 1177
43. T. Haikarainen J. Koivunen M. Narwal H. Venkannagari E. Obaji P. Joensuu T. Pihlajaniemi L. Lehtiö para-Substituted 2-phenyl-3,4-dihydroquinazolin-4-ones as potent and selective tankyrase inhibitors ChemMedChem 2013 8 1978 1985
44. E. Wahlberg T. Karlberg E. Kouznetsova N. Markova A. Macchiarulo A. G. Thorsell E. Pol A. Frostell T. Ekblad D. Oncü B. Kull G. M. Robertson R. Pellicciari H. Schüler J. Weigelt Family-wide chemical profiling and structural analysis of PARP and tankyrase inhibitors Nat. Biotechnol. 2012 30 283 288
45. P. Liscio A. Carotti S. Asciutti T. Karlberg D. Bellocchi L. Llacuna A. Macchiarulo S. A. Aaronson H. Schüler R. Pellicciari E. Camaioni Design, synthesis, crystallographic studies, and preliminary biological appraisal of new substituted triazolo[4,3-b]pyridazin-8-amine derivatives as tankyrase inhibitors J. Med. Chem. 2014 57 2807 2812
46. Y. Yashiroda R. Okamoto K. Hatsugai Y. Takemoto N. Goshima T. Saito M. Hamamoto Y. Sugimoto H. Osada H. Seimiya M. Yoshida A novel yeast cell-based screen identifies flavone as a tankyrase inhibitor Biochem. Biophys. Res. Commun. 2010 394 569 573
47. M. Narwal A. Fallarero P. Vuorela L. Lehtiö Homogeneous screening assay for human tankyrase J. Biomol. Screening 2012 17 593 604
48. M. Narwal T. Haikarainen A. Fallarero P. M. Vuorela L. Lehtiö Screening and structural analysis of flavones inhibiting tankyrases J. Med. Chem. 2013 56 3507 3517
49. M. Narwal J. Koivunen T. Haikarainen E. Obaji O. E. Legala H. Venkannagari P. Joensuu T. Pihlajaniemi L. Lehtiö Discovery of tankyrase inhibiting flavones with increased potency and isoenzyme selectivity J. Med. Chem. 2013 56 7880 7889