Structural features underlying the selectivity of the kinase inhibitors NBC and dNBC: Role of a nitro group that discriminates between CK2 and DYRK1A

Cellular and Molecular Life Sciences

Volumn 69, Issue 3, 2012, Pages 449-460

  Sarno, Stefania ^a,b   Mazzorana, Marco ^b,d   Traynor, Ryan ^c   Ruzzene, Maria ^a,b   Cozza, Giorgio ^a   Pagano, Mario A ^a   Meggio, Flavio ^a   Zagotto, Giuseppe ^a   Battistutta, Roberto ^a,b   Pinna, Lorenzo A ^a,b  

^a UNIVERSITY OF PADOVA   (Italy)

^b VENETIAN INSTITUTE OF MOLECULAR MEDICINE   (Italy)

^c UNIVERSITY OF DUNDEE   (United Kingdom)

^d DIAMOND LIGHT SOURCE LTD   (United Kingdom)

Author keywords

DYRK1A; Kinase inhibitors; PIM kinases; PKB; Protein kinase CK2

Indexed keywords

8 HYDROXY 4 METHYL 9 NITROBENZO(G)CHROMEN 2 ONE; ANTINEOPLASTIC AGENT; CASEIN KINASE II; DENITRO 8 HYDROXY 4 METHYL 9 NITROBENZO(G)CHROMEN 2 ONE; DUAL SPECIFICITY TYROSINE PHOSPHORYLATED AND REGULATED KINASE 1A; MEMBRANE PROTEIN; QUINALIZARIN; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; BINDING SITE; CANCER CELL; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG EFFICACY; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; ENZYME ACTIVE SITE; ENZYME INHIBITION; GENE EXPRESSION PROFILING; HUMAN; HUMAN CELL; IC 50; PROTEIN CLEAVAGE; PROTEIN PHOSPHORYLATION; PROTEIN PROTEIN INTERACTION; PROTEIN STRUCTURE;

ANIMALS; APOPTOSIS; BINDING SITES; CASEIN KINASE II; CELL LINE; CELL SURVIVAL; COUMARINS; CRYSTALLOGRAPHY, X-RAY; HUMANS; KINETICS; PROTEIN KINASE INHIBITORS; PROTEIN STRUCTURE, TERTIARY; PROTEIN-SERINE-THREONINE KINASES; PROTEIN-TYROSINE KINASES; PROTO-ONCOGENE PROTEINS; PROTO-ONCOGENE PROTEINS C-PIM-1; RATS; RECOMBINANT PROTEINS;

ZEA MAYS;

EID: 84856212076     PISSN: 1420682X     EISSN: 14209071     Source Type: Journal    
DOI: 10.1007/s00018-011-0758-7     Document Type: Article

References (38)

1. LA Hopkins CR Groom 2002 The druggable genome Nat Rev Drug Discov 1 727 730 12209152 10.1038/nrd892 1:CAS:528:DC%2BD38XmslamtrY%3D (Pubitemid 37361545)
2. G Manning DB Whyte R Martinez T Hunter S Sudarsanam 2002 The protein kinase complement of the human genome Science 298 1912 1934 12471243 10.1126/science.1075762 1:CAS:528:DC%2BD38Xpt1Wisb0%3D (Pubitemid 35425239)
3. M Salvi S Sarno L Cesaro H Nakamura LA Pinna 2009 Extraordinary pleiotropy of protein kinase CK2 revealed by weblogo phosphoproteome analysis Biochim Biophys Acta 1793 847 859 19339213 10.1016/j.bbamcr.2009.01.013 1:CAS:528:DC%2BD1MXmtVCjs7c%3D
4. M Salvi L Cesaro LA Pinna 2010 Variable contribution of protein kinases to the generation of the human phosphoproteome: a global weblogo analysis BioMol Concept 1 185 195 10.1515/BMC.2010.013
5. I Dominguez GE Sonenshein DC Seldin 2009 Protein kinase CK2 in health and disease: CK2 and its role in Wnt and NF-kB signalling: linking development and cancer Cell Mol Life Sci 66 1850 1857 19387549 10.1007/s00018-009-9153-z 1:CAS:528:DC%2BD1MXpsVGjs7s%3D
6. B Guerra O-G Issinger 2008 Protein kinase CK2 in human diseases Curr Med Chem 15 1870 1886 18691045 10.2174/092986708785132933 1:CAS:528: DC%2BD1cXhtVSrsL7N
7. S Sarno LA Pinna 2008 Protein kinase CK2 as a druggable target Mol Biosyst 4 889 894 18704226 10.1039/b805534c 1:CAS:528:DC%2BD1cXpvVSqs7w%3D
8. M Ruzzene LA Pinna 2010 Addiction to protein kinase CK2: a common denominator of diverse cancer cells? Biochim Biophys Acta 1804 499 504 19665589 1:CAS:528:DC%2BC3cXhs1ynu7k%3D
9. A Silva JA Yunes BA Cardoso LR Martins PY Jotta M Abecasis AE Nowill NR Leslie AA Cardoso JT Barata 2008 PTEN posttranslational inactivation and hyperactivation of the PI3 K/Akt pathway sustain primary T cell leukaemia viability J Clin Invest 118 3762 3764 18830414 10.1172/JCI34616 1:CAS:528:DC%2BD1cXhtlGltLjL
10. FA Piazza M Ruzzene C Gurrieri B Montini L Bonanni G Chioetto G Di Maira F Barbon A Cabrelle R Zambello F Adami L Trentin LA Pinna G Semenzato 2006 Multiple myeloma cell survival relies on high activity of protein kinase CK2 Blood 108 1698 1707 16684960 10.1182/blood-2005-11-013672 1:CAS:528: DC%2BD28Xpt1Slurw%3D (Pubitemid 44316140)
11. JS Kim JI Eom JW Cheong JK Lee WI Yang YM Min 2007 Protein kinase CK2alpha as an unfavourable prognostic marker and novel therapeutic target in acute myeloid leukaemia Clin Cancer Res 13 1019 1028 17289898 10.1158/1078-0432.CCR-06-1602 1:CAS:528:DC%2BD2sXhsVyku7c%3D (Pubitemid 46340381)
12. NL Solimini J Luo SJ Elledge 2007 Non-oncogene addiction and the stress phenotype of cancer cells Cell 130 986 988 17889643 10.1016/j.cell.2007.09.007 1:CAS:528:DC%2BD2sXhtFKnurvM (Pubitemid 47422308)
13. JH Trembley Z Chen G Unger J Slaton BT Kren C Van Waes K Ahmed 2010 Emergence of protein kinase CK2 as a key target in cancer therapy Biofactors 36 187 195 20533398 10.1002/biof.96 1:CAS:528:DC%2BC3cXht1ens7rF
14. S Sarno M Salvi R Battistutta G Zanotti LA Pinna 2005 Features and potentials of ATP-site directed CK2 inhibitors Biochim Biophys Acta 1754 263 270 16198160 1:CAS:528:DC%2BD2MXhtlags7bF (Pubitemid 41797707)
15. JS Duncan DW Litchfield 2008 Too much of a good thing: the role of protein kinase CK2 in tumorigenesis and prospects for therapeutic inhibition of CK2 Biochim Biophys Acta 1784 33 47 17931986 1:CAS:528:DC%2BD1cXptlCjsg%3D%3D
16. Sarno S, Papinutto E, Franchin C, Bain J, Elliott M, Meggio F, Kazimierczuk Z, Orzeszko A, Zanotti G, Battistutta R, Pinna LA (2010) ATP site-directed inhibitors of protein kinase CK2: an update. Curr Top Med Chem (in press)
17. M Mazzorana LA Pinna R Battistutta 2008 A structural insight into CK2 inhibition Mol Cell Biochem 316 57 62 18626746 10.1007/s11010-008-9822-5 1:CAS:528:DC%2BD1cXhtVansrnN
18. R Battistutta 2009 Protein kinase CK2 in health and disease: Structural bases of protein kinase CK2 inhibition Cell Mol Life Sci 66 1868 1889 19387547 10.1007/s00018-009-9155-x 1:CAS:528:DC%2BD1MXpsVGjs7k%3D
19. MA Pagano J Bain Z Kazimierczuk S Sarno M Ruzzene G Di Maira M Elliott A Orzeszko G Cozza F Meggio LA Pinna 2008 The selectivity of inhibitors of protein kinase CK2: an update Biochem J 415 353 365 18588507 10.1042/BJ20080309 1:CAS:528:DC%2BD1cXht1CmsrnJ
20. A Chilin R Battistutta A Bortolato G Cozza S Zanatta G Poletto M Mazzorana G Zagotto E Uriarte A Guiotto LA Pinna F Meggio S Moro 2008 Coumarin as attractive casein kinase 2 (CK2) inhibitor scaffold: an integrate approach to elucidate the putative binding motif and explain structure-activity relationships J Med Chem 51 752 759 18251491 10.1021/jm070909t 1:CAS:528:DC%2BD1cXhsFehs78%3D (Pubitemid 351304684)
21. F Meggio MA Pagano S Moro G Zagotto M Ruzzene S Sarno G Cozza J Bain M Elliott A Donella Deana AM Brunati LA Pinna 2004 Inhibition of protein kinase CK2 by condensed polyphenolic derivatives. An in vitro and in vivo study Biochemistry 43 12931 12936 15461466 10.1021/bi048999g 1:CAS:528: DC%2BD2cXnsFOiuro%3D (Pubitemid 39331813)
22. F Meggio A Donella Deana LA Pinna 1981 Endogenous phosphate acceptor proteins for rat liver cytosolic casein kinases J Biol Chem 256 11958 11961 6946060 1:CAS:528:DyaL38XivVag
23. S Sarno P Vaglio F Meggio O-G Issinger LA Pinna 1996 Protein kinase CK2 mutants defective in substrate recognition: purification and kinetic analysis J Biol Chem 271 10595 10601 8631861 10.1074/jbc.271.18.10595 1:CAS:528: DyaK28XivVaqtrg%3D (Pubitemid 26145793)
24. MA Pagano M Andrzejewska M Ruzzene S Sarno L Cesaro J Bain M Elliott F Meggio Z Kazimierczuk LA Pinna 2004 Optimization of protein kinase CK2 inhibitors derived from 4, 5, 6, 7-tetrabromobenzimidazole J Med Chem 47 6239 6247 15566294 10.1021/jm049854a 1:CAS:528:DC%2BD2cXpt1Sksbk%3D (Pubitemid 39587248)
25. J Bain L Plater M Elliott N Shpiro J Hastie H McLauchlan I Klevernic S Arthur D Alessi P Cohen 2007 The selectivity of protein kinase inhibitors; a further update Biochem J 408 297 315 17850214 10.1042/BJ20070797 1:CAS:528:DC%2BD2sXhtlGmtbjE
26. S Himpel W Tegge R Frank S Leder H-G Joost W Becker 2000 Specificity determinants of substrate recognition by the protein kinase DYRK1A J Biol Chem 275 2431 2438 10644696 10.1074/jbc.275.4.2431 1:CAS:528:DC%2BD3cXpvFCisg%3D%3D (Pubitemid 30082003)
27. PP Graczyk 2007 Gini coefficient: a new way to express selectivity of kinase inhibitors against a family of kinases J Med Chem 50 5773 5779 17948979 10.1021/jm070562u 1:CAS:528:DC%2BD2sXhtFyhu7rL (Pubitemid 350106032)
28. R Battistutta E De Moliner S Sarno G Zanotti LA Pinna 2001 Structural features underlying selective inhibition of protein kinase CK2 by ATP site-directed tetrabromo-2-benzotriazole Protein Sci 10 2200 2206 11604527 10.1110/ps.19601 1:CAS:528:DC%2BD3MXnvV2rsr0%3D (Pubitemid 32988637)
29. Leslie AGW (1991) Crystallographic Computing V. In: Moras D, Podjarny AD, Thierry, JP (eds) Crystallographic Computing 5, From Chemistry to Biology. Oxford University Press, Oxford, pp 27-38
30. Evans PR "Data reduction", Proceedings of CCP4 Study Weekend, 1993, on Data Collection & Processing, pp 114-122
31. Collaborative Computational Project, Number 4 (1994) The CCP4 Suite: Programs for Protein Crystallography. Acta Cryst D50: 760-763
32. PD Adams PV Afonine G Bunkóczi VB Chen IW Davis N Echols JJ Headd LW Hung GJ Kapral RW Grosse-Kunstleve AJ McCoy NW Moriarty R Oeffner RJ Read DC Richardson JS Richardson TC Terwilliger PH Zwart 2010 PHENIX: a comprehensive Python-based system for macromolecular structure solution Acta Crystallogr D Biol Crystallogr 66 213 221 20124702 10.1107/S0907444909052925
33. P Emsley B Lohkamp W Scott K Cowtan 2010 Features and Development of Coot Acta Crystallogr D Biol Crystallogr 66 486 501 20383002 10.1107/ S0907444910007493 1:STN:280:DC%2BC3c3lt1OqsQ%3D%3D
34. G Cozza P Bonvini E Zorzi G Poletto MA Pagano S Sarno A Donella-Deana G Zagotto A Rosolen LA Pinna 2006 Identification of ellagic acid as potent inhibitor of protein kinase CK2: a successful example of a virtual screening application J Med Chem 49 2363 2366 16610779 10.1021/jm060112m 1:CAS:528:DC%2BD28Xitl2itLY%3D
35. G Cozza M Mazzorana E Papinutto J Bain M Elliott G Di Maira A Gianoncelli MA Pagano S Sarno M Ruzzene R Battistutta F Meggio S Moro G Zagotto LA Pinna 2009 Quinalizarin as a potent, selective and cell-permeable inhibitor of protein kinase CK2 Biochem J 421 387 395 19432557 10.1042/BJ20090069 1:CAS:528:DC%2BD1MXosV2hurk%3D
36. E De Moliner S Moro S Sarno G Zagotto G Zanotti LA Pinna R Battistutta 2003 Inhibition of Protein Kinase CK2 by Anthraquinone-related Compounds J Biol Chem 278 1831 1836 12419810 10.1074/jbc.M209367200 (Pubitemid 36801420)
37. YS Ryu SY Park M-S Jung S-H Yoon M-Y Kwen S-Y Lee S-H Choi C Radnaabazar M-K Kim H Kim K Kim W-J Song S-H Chung 2010 Dyrk1A-mediated phosphorylation of prresenilin 1: a functional link between Down syndrome and Alzheimer's disease J Neurochem 115 574 584 20456003 10.1111/j.1471-4159.2010.06769.x 1:CAS:528:DC%2BC3cXhtlGlsb%2FJ
38. KA Ahmad G Wang G Unger J Slaton K Ahmed 2008 Protein Kinase CK2 - A Key Suppressor of Apoptosis Adv Enzyme Regul 48 179 187 18492491 10.1016/j.advenzreg.2008.04.002 1:CAS:528:DC%2BD1MXhsFGmtbrI