Evaluation of 4H-4-chromenone derivatives as inhibitors of protein kinase CK2

Biopolymers and Cell

Volumn 21, Issue 3, 2005, Pages 287-292

  Prykhod'ko, A O ^a   Yakovenko, O Ya ^a   Golub, A G ^a   Bdzhola, V G ^a   Yarmoluk, S M ^a  

^a INSTITUTE OF MOLECULAR BIOLOGY AND GENETICS   (Ukraine)

Author keywords

4H 4 chromenone; Chromone; CK2 kinase inhibitor; Receptor based design

Indexed keywords

EID: 84870472941     PISSN: 02337657     EISSN: 19936842     Source Type: Journal    
DOI: 10.7124/bc.0006F4     Document Type: Article

References (43)

1. Murray A. W. Recycling the cell cycle. Cyclins revisited // Cell.-2004.-116, N 2.-P. 221-234.
2. Kimmich R. D., Park W. K Chemical libraries towards protein kinase inhibitors // Comb. Chem. High Throughput Screen.-2003.-6, N 7.-P. 661-672.
3. Allende J. E., Alienee C. C. Protein kinase CK2: an enzyme with multiple substrates and a puzzling regulation // FASEB J.-1995.-9.-P. 313-323.
4. Pinna L. Protein Kinase CK2 // Int. J. Biochem. Cell. Biol.-1997.-29.-P. 551-554.
5. Marchiori F., Meggio F., Marin O., Borin G., Calderan A., Ruzza P., Pinna L. A. Synthetic peptide substrates for casein kinase 2. Assessment of minimum structural requirements for posphorylation // Biochlm. et Biophys. Acta.-1988.-971.-P. 332-338.
6. Marin O., Meggio F., Marchiori F., Borin G, Pinna L A. Site specificity of Casein Kinase-2 (TS) from rat liver cytosol. A study with model peptide substrates // Eur. J. Biochem.-1986.-160-P. 239-244.
7. Sheldin D. C, Leder P. Casein Kinase 2a transgene-induced murine lymphomas: relation to theilerosis in cattle // Science.-1995.-267.-P. 894-897.
8. Ravi R., Bedi A. Sensitization of tumor cells to Apo2 ligand/ TRAIL-induced apoptosis by inhibition of Casein Kinase 2 // Cancer Res-2002.-62.-P. 4180-4185.
9. Cotelle N. Role of flavonoids in oxidative stress // Curr. Top. Med. Chem.-2001.-1.-P. 569-590.
10. Van Acker F. A. A., Hageman J. A, Haenen G. R. M. M., Van der Vijgh W. J. F., Bast A., Menge W. M. P. B. Synthesis of novel 3,7-substituted-2-(3',4'-dihydroxyphenyl)flavones with improved antioxidant activity // J. Med. Chem.-2000.-43.-P. 3752-3760.
11. Owen R. W., Giacosa A., Hull W. E., Haubner R., Spiegelhalder B., Bartsch H. The antioxidant/anticancer potential of phenolic compounds isolated from olive oil // Eur. J. Cancer-2000-36.-P. 1235-1247.
12. Iing Y., Waxman S. Structural requirements for differentiation-induction and growth-inhibition of mouse erythroleukemia cells by isoflavones // Anticancer Res.-1995-15-P. 1147-1152.
13. Ren W., Qiao Z., Wang H., Zhu L., Zhang L, Lu Y., Cui Y., Zhang Z., Wang Z. Tartary buckwheat flavonoid activites caspase 3 and induces HL-60 cell apoptosis // Meth. Find Exp. Clin. Pharmacol.-2001.-23.-P. 427-432.
14. Wenzel U., Kuntz S., Brendel M. D., Daniel H. Dietary flavone is a potent apoptosis inducer in human colon carcinoma cells // Cancer Res.-2000.-60.-P. 3823-3831.
15. Wang I. K, Lin-Shiau S. Y., Lin J. K. Induction of apoptosis by apigenin and related flavonoids through cytochrome c release and activation of caspase-9 and caspase-3 in leukemia HL-60 cells // Eur. J. Cancer.-2000.-35.-P. 1517-1525.
16. Ko W. G., Kang T. H, Lee S. J., Kim N. Y., Kim Y. C, Sohn D. H., Lee B. H. Polymethoxyflavonoids from Vitex rotundifolia inhibit proliferation by inducing apoptosis in human myeloid leukemia cells // Food Chem. Toxicol.-2000.-38.-P. 861-865.
17. Traxler P., Green J., Mett H., Sequin U., Furet P. Use of a pharmacophore model for the design of EGFR tyrosine kinase inhibitors: isoflavones and 3-phenyl-4(lH)-quinolones // J. Med. Chem.-1999.-42.-P. 1018-1026.
18. Geahlen R. L, Koonchanok N. M., McLaughlin J. L, Pratt D. E. Inhibition of protein-tyrosine kinase activity by flavonoids and related compounds // J. Nat. Prod.-1989.-52.-P. 982-986.
19. Cushman M., Nagarathnam D., Burg D. L, Geahlen R. L Synthesis and protein-tyrosine kinase inhibitory activities of flavonoid analogues // J. Med. Chem.-1991.-34.-P. 798-806.
20. Srivastava A. K Inhibition of phosphorylase kinase, and tyrosine protein kinase activities by quercetin // Biochem. and Biophys. Res. Communs-1985.-131-P. 1-5.
21. Lopez-Lazaro M., Martin-Cordero C, Tow M. V., Ayuso M. J. Flavonoids as DNA topoisomerase I poisons // J. Enzyme Inhib. Med. Chem.-2002.-17.-P. 25-29.
22. Lopez-Lazaro M., Martin-Cordero C, Ayuso M. J. Two new flavonol glycosides as DNA topoisomerase I poisons // Z. Naturforsch.-2000.-55.-P. 898-902.
23. Gamet-Payrastre L, Manenti S., Gratacap M. P., Tulliez J., Chap H., Payrastre B. Flavonoids and the inhibition of PKC and PI 3-kinase // Gen. Pharmacol.-1999-32,-P. 279-286.
24. Agullo G, Gamet-Payrastre L, Manenti S., Viala C, Retnesy C, Chap H., Payrastre B. Relationship between flavonoid structure and inhibition of phosphatidylinositol 3-kinase: a comparison with tyrosine kinase and protein kinase C inhibition // Biochem. Pharmacol.-1997.-53.-P. 1649-1657.
25. Ferriola P. G, Cody V., Middleton E., Jr. Protein kinase C inhibition by plant flavonoids. Kinetic mechanism and structure-activity relationships // Biochem. Pharmacol.-1989.-38.-P. 1617-1624.
26. Casagrande F., Darbon J. M. Effects of structurally related flavonoids on cell cycle progression of human melanoma cells: regulation of cyclin-dependent kinases CDK2 and CDK1 // Biochem. Pharmacol.-2001.-61.-P. 1205-1215.
27. Sarno S., Moro S., Meggio F., Zagotto G, Dal Ben D., Ghisellini P., Battistutta R., Zanotti G., Pinna L A. Toward the rational design of protein kinase casein kinase-2 inhibitors // Pharmacol, and Therapeut.-2002.-93.-P. 159-168.
28. Battistutta R., De Moliner E., Sarno S., Zanotti G., Pinna L. A. Structural features underlying selective inhibition of protein kinase CK2 by ATP-site directed tetrabromo-benzotriazole // Protein Sci.-2001.-10.-P. 2200-2206.
29. Battistutta R., Sarno S., De Moliner E., Papinutto E., Zanotti G, Pinna L A. The replacement of ATP by the competitive inhibitor emodin induces conformational modifications in the catalytic site of protein Kinase CK2 // J. Biol. Chem.-2000.-275, N 38.-P. 29618-29622.
30. Filikov A. V., James T. L Structure-based design of ligands for protein basic domains: application to the HIV-1 Tat protein // J. Comput.-Aided Mol. Des.-1998.-12.-P. 229-240.
31. Shoichet B. K., Stroud R. M., Santi D. V., Kuntz I. D., Perry K. M. Structure-based discovery of inhibitors of thymidylate synthase // Science.-1993.-259.-P. 1445-1450.
32. Bodian D. L, Yamasaki R. B., Buswell R. L, Stearns J. F., White J. M., Kuntz I. D. Inhibition of the fusion-inducing conformational change of influenza hemagglutinin by benzoquinones and hydroquinones // Biochemistry.-1993-32.-P. 2967-2978.
33. Ring C. S., Sun E., McKerrow J. H., Lee G. K, Rosenthal P. J., Kuntz I. D., Cohen F. E. Structure-based inhibitor design by using protein models for the development of antiparasitic agents // Proc. Nat. Acad. Sci. USA.-1993-90-P. 3583-3587.
34. Schmidt M. W., Baldridge K K, Boatz J. A., Elbert S. T, Gordon M. S., Jensen J. H., Koseki S., Matsunaga N., Nguyen K A., Su S., Windus T. L The general atomic and molecular electronic structure system // J. Comp. Chem.-1993.-14.-P. 1347-1358.
35. Lindahl E., Hess B., van der Spoel D. GROMACS 3.0: a package for molecular simulation and trajectory analysis // Mol. Mod.-2001.-7.-P. 306-317.
36. Ewing T. J. A., Kuntz J. D. Critical evaluation of search algorithms for automated molecular docking and database screening // J. Comput. Chem.-1996.-18, N 9.-P. 1175-1189.
37. Bursulaya B. D., Totrov M., Abagyan R., Brooks III C. L. Comparative study of several algorithms for flexible ligand docking // J. Comput.-Aided Mol. Des-2003-17, N 11.-P. 755-763.
38. Vasitev S. A., Luk'yanchykov M. S., Molchanov G. I., Turubarov V. D., Khilya V. P. Synthesis and biological properties of 3-phenoxychromones and 3-phenoxy-4-hydroxy-7-methoxycumarine // Khim.-pharm. zhurn.-1991.-7.-P. 34-38 (in Russian).
39. Arkhipov V. V., Smirnov M. N., Khilya V. P. Chemistry of modified flavonoids. 19. Synthesis of phenoxyl analogs of isoflavone // Chem. Heterocycl. Comp.-1997.-359.-P. 598-603 (in Russian).
40. Garazd M. M., Arkhipov V. V., Proskurka N. K, Khilya V. P. Chemistry of isoflavonoid hetero analogs. 23. Synthesis of aminoacyl derivatives of 3-phenoxychromone // Chem. Heterocycl. Comp.-1999.-384.-P. 744-748 (in Russian).
41. De Moliner E., Sarno S., Moro S., Zanotti G, Battistutta R, Pinna L A. Inhibition of protein kinase CK2 by anthraquinone-related compounds. A structural insight // J. Biol. Chem.-2003.-278.-P. 1831-1836.
42. Sarno S., De Moliner E., Ruzzene M., Pagano M. A., Battistutta R., Bain J., Fabbro D., Schoepfer J., Elliott M., Furet P., Meggio F., Zanotti G., Pinna L A. Biochemical and three-dimensional-structural study of the specific inhibition of protein kinase CK2 by [5-oxo-5,6-dihydroindolo-(l,2-A)quinazolin-7-Yl] acetic acid (Iqa) // Biochem. J.-2003.-374.-P. 639-646.
43. Vangrevelinghe E., Zimmermann K., Schoepfer J., Portmann R., Fabbro D. Furet P. Discovery of a potent and selective protein kinase CK2 inhibitor by high-throughput docking // J. Med. Chem-2003.-46.-P. 26560-2662.