Structure-function correlation of G6, a novel small molecule inhibitor of Jak2: Indispensability of the stilbenoid core

Journal of Biological Chemistry

Volumn 285, Issue 41, 2010, Pages 31399-31407

  Majumder, Anurima ^a   Govindasamy, Lakshmanan ^a   Magis, Andrew ^b   Kiss, Róbert ^c   Polgár, Tímea ^d   Baskin, Rebekah ^a   Allan, Robert W ^a   Agbandje McKenna, Mavis ^a   Reuther, Gary W ^e   Keseru, György M ^d   Bisht, Kirpal S ^f   Sayeski, Peter P ^a  

^a UNIVERSITY OF FLORIDA COLLEGE OF MEDICINE   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^c HERIOT WATT UNIVERSITY   (United Kingdom)

^d BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^e H LEE MOFFITT CANCER CENTER AND RESEARCH INSTITUTE   (United States)

^f UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BONE; CELL DEATH; CELL GROWTH; CELL PROLIFERATION; GROWTH KINETICS; MOLECULES; PATHOLOGY; PHOSPHORYLATION;

APOPTOSIS; APOPTOTIC PATHWAYS; ATP-BINDING; DOSE-DEPENDENT MANNER; ERYTHROLEUKEMIA CELLS; EX-VIVO; HUMAN BONE MARROW CELLS; JAK/STAT; KINASE DOMAINS; SMALL MOLECULE INHIBITOR; SOMATIC MUTATION; STRUCTURAL SIMILARITY; STRUCTURE-BASED; STRUCTURE-FUNCTION CORRELATION; VIRTUAL SCREENING;

LEAD COMPOUNDS;

ADENOSINE TRIPHOSPHATE; D21 (DRUG); D23 (DRUG); D25 (DRUG); D28 (DRUG); D30 (DRUG); G6; JANUS KINASE 2; JANUS KINASE 2 INHIBITOR; PHENYLALANINE; STAT3 PROTEIN; STAT5 PROTEIN; STILBENE DERIVATIVE; UNCLASSIFIED DRUG; VALINE; JAK2 PROTEIN, HUMAN; PROTEIN KINASE INHIBITOR; STAT3 PROTEIN, HUMAN;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BONE MARROW CELL; CANCER INHIBITION; CELL GROWTH; CELL PROLIFERATION; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DOSE TIME EFFECT RELATION; ERYTHROLEUKEMIA CELL; EX VIVO STUDY; FEMALE; HUMAN; HUMAN CELL; MOLECULAR DOCKING; PRIORITY JOURNAL; PROTEIN DOMAIN; PROTEIN EXPRESSION; PROTEIN PHOSPHORYLATION; STRUCTURAL HOMOLOGY; STRUCTURE ACTIVITY RELATION; AMINO ACID SUBSTITUTION; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; ENZYMOLOGY; GENETICS; METABOLISM; MISSENSE MUTATION; POLYCYTHEMIA VERA; TUMOR CELL LINE;

AMINO ACID SUBSTITUTION; APOPTOSIS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; JANUS KINASE 2; MUTATION, MISSENSE; POLYCYTHEMIA VERA; PROTEIN KINASE INHIBITORS; STAT3 TRANSCRIPTION FACTOR; STAT5 TRANSCRIPTION FACTOR; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77957783233     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M110.168211     Document Type: Article

References (45)

1. Parganas, E., Wang, D., Stravopodis, D., Topham, D. J., Marine, J. C., Teglund, S., Vanin, E. F., Bodner, S., Colamonici, O. R., van Deursen, J. M., Grosveld, G., and Ihle, J. N. (1998) Cell 93, 385-395
2. Neubauer, H., Cumano, A., Müller, M., Wu, H., Huffstadt, U., and Pfeffer, K. (1998) Cell 93, 397-409
3. Peeters, P., Raynaud, SD., Cools, J., Wlodarska, I., Grosgeorge, J., Philip, P., Monpoux, F., Van Rompaey, L., Baens, M., Van den Berghe, H., and Marynen, P. (1997) Blood 90, 2535-2540
4. Joos, S., Granzow, M., Holtgreve-Grez, H., Siebert, R., Harder, L., Martín-Subero, J. I., Wolf, J., Adamowicz, M., Barth, T. F., Lichter, P., and Jauch, A. (2003) Int. J. Cancer 103, 489-495
5. Reiter, A., Walz, C., Watmore, A., Schoch, C., Blau, I., Schlegelberger, B., Berger, U., Telford, N., Aruliah, S., Yin, J. A., Vanstraelen, D., Barker, H. F., Taylor, P. C., O'Driscoll, A., Benedetti, F., Rudolph, C., Kolb, H. J., Hochhaus, A., Hehlmann, R., Chase, A., and Cross, N. C. (2005) Cancer Res. 65, 2662-2667
6. Griesinger, F., Hennig, H., Hillmer, F., Podleschny, M., Steffens, R., Pies, A., Wörmann, B., Haase, D., and Bohlander, S. K. (2005) Genes Chromosomes Cancer 44, 329-333
7. Baxter, E. J., Scott, L. M., Campbell, P. J., East, C., Fourouclas, N., Swanton, S., Vassiliou, G. S., Bench, A. J., Boyd, E. M., Curtin, N., Scott, M. A., Erber, W. N., and Green, A. R. (2005) Lancet 365, 1054-1061
8. James, C., Ugo, V., Le Couédic, J. P., Staerk, J., Delhommeau, F., Lacout, C., Garçon, L., Raslova, H., Berger, R., Bennaceur-Griscelli, A., Villeval, J. L., Constantinescu, S. N., Casadevall, N., and Vainchenker, W. (2005) Nature 434, 1144-1148
9. Kralovics, R., Passamonti, F., Buser, A. S., Teo, S. S., Tiedt, R., Passweg, J. R., Tichelli, A., Cazzola, M., and Skoda, R. C. (2005) N. Engl. J. Med. 352, 1779-1790
10. Levine, R. L., Wadleigh, M., Cools, J., Ebert, B. L., Wernig, G., Huntly, B. J., Boggon, T. J., Wlodarska, I., Clark, J. J., Moore, S., Adelsperger, J., Koo, S., Lee, J. C., Gabriel, S., Mercher, T., D'Andrea, A., Fröhling, S., Döhner, K., Marynen, P., Vandenberghe, P., Mesa, R. A., Tefferi, A., Griffin, J. D., Eck, M. J., Sellers, W. R., Meyerson, M., Golub, T. R., Lee, S. J., and Gilliland, D. G. (2005) Cancer Cell 7, 387-397
11. Zhao, R., Xing, S., Li, Z., Fu, X., Li, Q., Krantz, S. B., and Zhao, Z. J. (2005) J. Biol. Chem. 280, 22788-22792
12. Kiss, R., Polgár, T., Kirabo, A., Sayyah, J., Figueroa, N. C., List, A. F., Sokol, L., Zuckerman, K. S., Gali, M., Bisht, K. S., Sayeski, P. P., and Keseru, G. M. (2009) Bioorg. Med. Chem. Lett. 19, 3598-3601
13. Le Corre, L., Chalabi, N., Delort, L., Bignon, Y. J., and Bernard-Gallon, D. J. (2005) Mol. Nutr. Food Res. 49, 462-471
14. Larrosa, M., Tomás-Barberán, F. A., and Espín, J. C. (2004) Eur. J. Nutr. 43, 275-284
15. Kimura, Y. (2005) In Vivo 19, 37-60
16. Gosslau, A., Chen, M., Ho, C. T., and Chen, K. Y. (2005) Br. J. Cancer 92, 513-521
17. Belleri, M., Ribatti, D., Nicoli, S., Cotelli, F., Forti, L., Vannini, V., Stivala, L. A., and Presta, M. (2005) Mol. Pharmacol. 67, 1451-1459
18. Pradhan, A., Lambert, Q. T., Griner, L. N., and Reuther, G. W. (2010) J. Biol. Chem. 285, 16651-16663
19. Kuntz, I. D., Blaney, J. M., Oatley, S. J., Langridge, R., and Ferrin, T. E. (1982) J. Mol. Biol. 161, 269-288
20. Lang, P. T., Brozell, S. R., Mukherjee, S., Pettersen, E. F., Meng, E. C., Thomas, V., Rizzo, R. C., Case, D. A., James, T. L., and Kuntz, I. D. (2009) RNA 15, 1219-1230
21. Antonysamy, S., Hirst, G., Park, F., Sprengeler, P., Stappenbeck, F., Steensma, R., Wilson, M., and Wong, M. (2009) Bioorg. Med. Chem. Lett. 19, 279-282
22. Schüttelkopf, A. W., and van Aalten, D. M. (2004) Acta. Crystallogr D. Biol. Crystallogr. 60, 1355-1363
23. Pettersen, E. F., Goddard, T. D., Huang, C. C., Couch, G. S., Greenblatt, D. M., Meng, E. C., and Ferrin, T. E. (2004) J. Comput. Chem. 25, 1605-1612
24. Emsley, P., and Cowtan, K. (2004) Acta. Crystallogr. D. Biol. Crystallogr. 60, 2126-2132
25. Baker, N. A., Sept, D., Joseph, S., Holst, M. J., and McCammon, J. A. (2001) Proc. Natl. Acad. Sci. U.S.A. 98, 10037-10041
26. DeLano, W. (2002) PyMOL Molecular Graphics System, DeLano Scientific, San Carlos, CA
27. Martin, P., and Papayannopoulou, T. (1982) Science 216, 1233-1235
28. Quentmeier, H., MacLeod, R. A., Zaborski, M., and Drexler, H. G. (2006) Leukemia 20, 471-476
29. Walz, C., Crowley, B. J., Hudon, H. E., Gramlich, J. L., Neuberg, D. S., Podar, K., Griffin, J. D., and Sattler, M. (2006) J. Biol. Chem. 281, 18177-18183
30. Bromberg, J. (2002) J. Clin. Invest. 109, 1139-1142
31. Baker, S. J., Rane, S. G., and Reddy, E. P. (2007) Oncogene. 26, 6724-6737
32. Socolovsky, M., Fallon, A. E., Wang, S., Brugnara, C., and Lodish, H. F. (1999) Cell 98, 181-191
33. Antonsson, B., and Martinou, J. C. (2000) Exp. Cell Res. 256, 50-57
34. Gross, A., Yin, X. M., Wang, K., Wei, M. C., Jockel, J., Milliman, C., Erdjument-Bromage, H., Tempst, P., and Korsmeyer, S. J. (1999) J. Biol. Chem. 274, 1156-1163
35. Lindauer, K., Loerting, T., Liedl, K. R., and Kroemer, R. T. (2001) Protein Eng. 14, 27-37
36. Lucet, I. S., Fantino, E., Styles, M., Bamert, R., Patel, O., Broughton, S. E., Walter, M., Burns, C. J., Treutlein, H., Wilks, A. F., and Rossjohn, J. (2006) Blood 107, 176-183
37. Biondi, R. M., Komander, D., Thomas, C. C., Lizcano, J. M., Deak, M., Alessi, D. R., and van Aalten, D. M. (2002) EMBO J. 21, 4219-4228
38. Favelyukis, S., Till, J. H., Hubbard, S. R., and Miller, W. T. (2001) Nat. Struct. Biol. 8, 1058-1063
39. Lougheed, J. C., Chen, R. H., Mak, P., and Stout, T. J. (2004) J. Biol. Chem. 279, 44039-44045
40. Till, J. H., Ablooglu, A. J., Frankel, M., Bishop, S. M., Kohanski, R. A., and Hubbard, S. R. (2001) J. Biol. Chem. 276, 10049-10055
41. Pace-Asciak, C. R., Hahn, S., Diamandis, E. P., Soleas, G., and Goldberg, D. M. (1995) Clin. Chim. Acta. 235, 207-219
42. Dodds, E. C., Goldberg, L., Lawson, W., and Robinson, R. (1938) Nature 141, 247-248
43. Geahlen, R. L., and McLaughlin, J. L. (1989) Biochem. Biophys. Res. Commun. 165, 241-245
44. Swanson-Mungerson, M., Ikeda, M., Lev, L., Longnecker, R., and Portis, T. (2003) J. Antimicrob. Chemother. 52, 152-154
45. Akwabi-Ameyaw, A., Bass, J. Y., Caldwell, R. D., Caravella, J. A., Chen, L., Creech, K. L., Deaton, D. N., Jones, S. A., Kaldor, I., Liu, Y., Madauss, K. P., Marr, H. B., McFadyen, R. B., Miller, A. B., Iii, F. N., Parks, D. J., Spearing, P. K., Todd, D., Williams, S. P., and Wisely, G. B. (2008) Bioorg. Med. Chem. Lett. 18, 4339-4343