Structure-based discovery of novel flavonol inhibitors of human protein kinase CK2

Molecular and Cellular Biochemistry

Volumn 356, Issue 1-2, 2011, Pages 107-115

  Golub, Andriy G ^a   Bdzhola, Volodymyr G ^a   Kyshenia, Yaroslav V ^a   Sapelkin, Vladislav M ^a   Prykhod'ko, Andriy O ^a   Kukharenko, Olexander P ^a   Ostrynska, Olga V ^a   Yarmoluk, Sergiy M ^a,b  

^a INSTITUTE OF MOLECULAR BIOLOGY AND GENETICS   (Ukraine)

^b Otava Ltd   (Ukraine)

Author keywords

3 hydroxy 4 carboxyflavones; Ck2 inhibitors; Flavonols; Molecular dynamics; Protein kinase; Virtual screening

Indexed keywords

3 HYDROXY 40 CARBOXYFLAVONE; ADENOSINE TRIPHOSPHATE; CASEIN KINASE II; FLAVONOL DERIVATIVE; PROTEIN SERINE THREONINE KINASE INHIBITOR; QUERCETIN; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; IN VITRO STUDY; MOLECULAR INTERACTION; MOLECULAR MODEL; NUCLEOTIDE BINDING SITE; STRUCTURE ACTIVITY RELATION;

CASEIN KINASE II; CATALYTIC DOMAIN; DRUG DISCOVERY; FLAVONOLS; HUMANS; HYDROGEN BONDING; KINETICS; MOLECULAR DYNAMICS SIMULATION; PROTEIN KINASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; THERMODYNAMICS;

EID: 84855231179     PISSN: 03008177     EISSN: 15734919     Source Type: Journal    
DOI: 10.1007/s11010-011-0945-8     Document Type: Article

References (36)

1. Johnson LN (2009) Protein kinase inhibitors: contributions from structure to clinical compounds. Q Rev Biophys 42(1):1-40
2. St-Denis NA, Litchfield DW (2009) Protein kinase CK2 in health and disease: From birth to death: the role of protein kinase CK2 in the regulation of cell proliferation and survival. Cell Mol Life Sci 66:1817-1829
3. Trembley JH, Chen Z, Unger G, Slaton J, Kren BT, Van Waes C, Ahmed K (2010) Emergence of protein kinase CK2 as a key target in cancer therapy. Biofactors 36(3):187-195
4. Wang G, Ahmad KA, Ahmed K (2005) Modulation of death receptor mediated apoptosis by CK2. Mol Cell Biochem 274(1-2):201-205 (Pubitemid 41001516)
5. Tawfic S, Yu S, Wang H, Faust R, Davis A, Ahmed K (2001) Protein kinase CK2 signal in neoplasia. Histol Histopathol 16(2):573-582 (Pubitemid 32297655)
6. Zhu D, Hensel J, Hilgraf R, Abbasian M, Pornillos O, Deyanat-Yazdi G, Hua XH, Cox S (2010) Inhibition of protein kinase CK2 expression and activity blocks tumor cell growth. Mol Cell Biochem 333(1-2):159-167
7. Marin O, Sarno S, Boschetti M, Pagano MA, Meggio F, Ciminale V, D'Agostino DM, Pinna LA (2000) Unique features of HIV-1 Rev protein phosphorylation by protein kinase CK2 ("casein kinase-2"). FEBS Lett 481:63-67 (Pubitemid 30662378)
8. Chien WM, Parker JN, Schmidt-Grimminger DC, Broker TR, Chow LT (2000) Casein kinase II phosphorylation of the human papillomavirus-18 E7 protein is critical for promoting S-phase entry. Cell Growth Differ 11:425-435 (Pubitemid 30644366)
9. Massimi P, Banks L (2000) Differential phosphorylation of the HPV-16 E7 oncoprotein during the cell cycle. Virology 276:388-394
10. Medina-Palazon C, Gruffat H, Mure F, Filhol O, Vingtdeux-Didier V, Drobecq H, Cochet C, Sergeant N, Sergeant A, Manet E (2007) Protein kinase CK2 phosphorylation of EB2 regulates its function in the production of Epstein-Barr virus infectious viral particles. J Virol 81:11850-11860 (Pubitemid 47623817)
11. Jung DH, Park HJ, Byun HE, Park YM, Kim TW, Kim BO, Um SH, Pyo S (2010) Diosgenin inhibits macrophage-derived inflammatory mediators through downregulation of CK2, JNK, NF-kappaB and AP-1 activation. Int Immunopharmacol 10(9):1047-1054
12. Yamada M, Katsuma S, Adachi T, Hirasawa A, Shiojima S, Kadowaki T, Okuno Y, Koshimizu TA, Fujii S, Sekiya Y, Miyamoto Y, Tamura M, Yumura W, Nihei H, Kobayashi M, Tsujimoto G (2005) Inhibition of protein kinase CK2 prevents the progression of glomerulonephritis. Proc Natl Acad Sci USA 102(21):7736-7741 (Pubitemid 40741040)
13. Pierre F, Chua PC, O'Brien SE, Siddiqui-Jain A, Bourbon P, Haddach M, Michaux J, Nagasawa J, Schwaebe MK, Stefan E, Vialettes A, Whitten JP, Chen TK, Darjania L, Stansfield R, Anderes K, Bliesath J, Drygin D, Ho C, Omori M, Proffitt C, Streiner N, Trent K, Rice WG, Ryckman DM (2011) Discovery and SAR of 5-(3-Chlorophenylamino)benzo[c][2,6]naphthyridine-8-carboxylic acid (CX-4945), the first clinical stage inhibitor of protein kinase CK2 for the treatment of cancer. J Med Chem 54(2):635-654
14. Cozza G, Bortolato A, Moro S (2010) How druggable is protein kinase CK2? Med Res Rev 30(3):419-462
15. Middleton E, Kandaswami C (1994) The impact of plant flavonoids on mammalian biology: implications for immunity, inflammation and cancer. In: Harborne JB (ed) The flavonoids advances in research since. Chapman & Hall, London, pp 619-652
16. Sarno S, Moro S, Meggio F, Zagotto G, Dal Ben D, Ghisellini P, Battistuta R, Zanotti G, Pinna L (2002) Toward the rational design of protein kinase casein kinase-2 inhibitors. Pharmacol Ther 93:159-168 (Pubitemid 34615557)
17. Shoichet BK, Stroud RM, Santi DV, Kuntz ID, Perry KM (1993) Structure-based discovery of inhibitors of thymidylate synthase. Science 259:1445-1450 (Pubitemid 23101379)
18. Bodian DL, Yamasaki RB, Buswell RL, Stearns JF, White JM, Kuntz ID (1993) Inhibition of the fusion-inducing conformational change of influenza hemagglutinin by benzoquinones and hydroquinones. Biochemistry 32:2967-2978 (Pubitemid 23110138)
19. Ring CS, Sun E, McKerrow JH, Lee GK, Rosenthal PJ, Kuntz ID, Cohen FE (1993) Structure-based inhibitor design by using protein models for the development of antiparasitic agents. Proc Natl Acad Sci USA 90:3583-3587 (Pubitemid 23111411)
20. Ewing TJ, Makino S, Skillman AG, Kuntz ID (2001) DOCK 4.0: search strategies for automated molecular docking of flexible molecule databases. J Comput Aided Mol Des 15:411-428 (Pubitemid 32452109)
21. OYa Yakovenko, Oliferenko AA, Golub AG, Bdzhola VG, Yarmoluk SM (2007) The new method of distribution integrals evaluations for high throughput virtual screening. Ukrainica Bioorganica Acta 1:52-62
22. Yakovenko O, Oliferenko AA, Bdzhola VG, Palyulin VA, Zefirov NS (2008) Kirchhoff atomic charges fitted to multipole moments: implementation for a virtual screening system. J Comput Chem 29(8):1332-1343 (Pubitemid 351594478)
23. Lindahl E, Hess B, van der Spoel D (2001) GROMACS 3.0: a package for molecular simulation and trajectory analysis. J Mol Mod 7:306-317 (Pubitemid 36153547)
24. Oostenbrink C, Villa A, Mark AE, Van Gunsteren WF (2004) A biomolecular force field based on the free enthalpy of hydration and solvation: The GROMOS force-field parameter sets 53A5 and 53A6. J Comput Chem 25(13):1656-1676
25. Hockney RW, Goel SP, Eastwood J (1974) Quiet high resolution computer models of a plasma. J Comput Phys 14:148-158
26. Darden T, Perera L, Li L, Pedersen L (1999) New tricks for modelers from the crystallography toolkit: the particle mesh Ewald algorithm and its use in nucleic acid simulations. Structure 7:55-60
27. Moorthy NSHN, Singh RJ, Singh HP, Gupta SD (2006) Synthesis, biological evaluation and in silico metabolic and toxicity prediction of some flavanrone derivatives. Chem Pharm Bull 54(10):1384-1390 (Pubitemid 44506568)
28. Bennett CJ, Caldwell ST, McPhail DB, Morrice PC, Duthie GG, Hartley RC (2004) Potential therapeutic antioxidants that combine the radical scavenging ability of myricetin and the lipophilic chain of vitamin E to effectively inhibit microsomal lipid peroxidation. Bioorg Med Chem 12(9):2079-2098 (Pubitemid 38471700)
29. Golub AG, Yakovenko OY, Prykhod'ko AO, Lukashov SS, Bdzhola VG, Yarmoluk SM (2008) Evaluation of 4,5,6,7-tet-rahalogeno-1H-isoindole-1, 3(2H)-diones as inhibitors of human protein kinase CK2. Biochim Biophys Acta 1784(1):143-149
30. Golub AG, Yakovenko OY, Bdzhola VG, Sapelkin VM, Zien P, Yarmoluk SM (2006) Evaluation of 3-Carboxy-4(1H)-quinolones as Inhibitors of Human Protein Kinase CK2. J Med Chem 49(22):6443-6450 (Pubitemid 44657440)
31. Golub AG, Bdzhola VG, Briukhovetska NV, Balanda AO, Kukharenko OP, Kotey IM, Ostrynska OV, Yarmoluk SM (2011) Synthesis and biological evaluation of substituted (thieno[2, 3-d]pyrimidin-4-ylthio)carboxylic acids as inhibitors of human protein kinase CK2. Eur J Med Chem 46:870-876
32. Vangrevelinghe E, Zimmermann K, Schoepfer J, Portmann R, Fabbro D, Furet P (2003) Discovery of a potent and selective protein kinase CK2 inhibitor by high-throughput docking. J Med Chem 46(13):2656-2662 (Pubitemid 36702534)
33. Pagano MA, Poletto G, Di Maira G, Cozza G, Ruzzene M, Sarno S, Bain J, Elliott M, Moro S, Zagotto G, Meggio F, Pinna LA (2007) Tetrabromocinnamic acid (TBCA) and related compounds represent a new class of specific protein kinase CK2 inhibitors. Chembiochem 8(1):129-139 (Pubitemid 46121580)
34. Sarno S, Salvi M, Battistutta R, Zanotti G, Pinna LA (2005) Features and potentials of ATP-site directed CK2 inhibitors. Biochim Biophys Acta 1754:263-270 (Pubitemid 41797707)
35. Sarno S, De Moliner E, Ruzzene M, Pagano MA, Battistutta R, Bain J, Fabbro D, Schoepfer J, Elliott M, Furet P, Meggio F, Zanotti G, Pinna LA (2003) Biochemical and three-dimensional-structural study of the specific inhibition of protein kinase CK2 by [5-Oxo-5, 6-dihydroindolo-(1, 2-a)quinazolin-7-yl]acetic acid (IQA). Biochem J 374:639-646 (Pubitemid 37163909)
36. Ferguson AD, Sheth PR, Basso AD, Paliwal S, Gray K, Fischmann TO, Le HV (2011) Structural basis of CX-4945 binding to human protein kinase CK2. FEBS Lett 585(1):104-110