IRC-083864, a novel bis quinone inhibitor of CDC25 phosphatases active against human cancer cells

International Journal of Cancer

Volumn 124, Issue 6, 2009, Pages 1449-1456

  Brezak, Marie Christine ^a   Valette, Annie ^b   Quaranta, Muriel ^b   Contour Galcera, Marie Odile ^a   Jullien, Denis ^b   Lavergne, Olivier ^a   Frongia, Céline ^b   Bigg, Dennis ^a   Kasprzyk, Philip G ^c   Prevost, Grégoire Pierre ^a   Ducommun, Bernard ^b,d  

^a Institut Henri Beaufour   (France)

^b UNIVERSITÉ DE TOULOUSE   (France)

^c Biomeasure Inc   (United States)

^d CHU PURPAN   (France)

Author keywords

Cancer; CDC25 phosphatase; Cell cycle; Pharmacology

Indexed keywords

IRC 083864; PROTEIN P21; PROTEIN TYROSINE PHOSPHATASE; PROTEIN TYROSINE PHOSPHATASE INHIBITOR; QUINONE DERIVATIVE; UNCLASSIFIED DRUG; 2 (2,5 DIFLUOROPHENYL) 6 ((3 (METHYL(3 ((2 METHYL 4,7 DIOXO 4,7 DIHYDRO 1,3 BENZOTHIAZOL 5 YL)AMINO)PROPYL)AMINO)PROPYL)AMINO) 1,3 BENZOXAZOLE 4,7 DIONE; 2-(2,5-DIFLUOROPHENYL)-6-((3-(METHYL(3-((2-METHYL-4,7-DIOXO-4,7-DIHYDRO-1,3-BENZOTHIAZOL-5-YL)AMINO)PROPYL)AMINO)PROPYL)AMINO)-1,3-BENZOXAZOLE-4,7-DIONE; BENZOTHIAZOLE DERIVATIVE; BENZOXAZOLE DERIVATIVE; CYCLIN DEPENDENT KINASE; ENZYME INHIBITOR;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL; CANCER CELL CULTURE; CANCER INHIBITION; CELL ASSAY; CELL CYCLE REGULATION; CELL STRAIN HCT116; CONTROLLED STUDY; DOSE RESPONSE; DRUG IDENTIFICATION; DRUG POTENCY; DRUG SELECTIVITY; ENZYME ASSAY; ENZYME INHIBITION; FEMALE; HUMAN; HUMAN CELL; MALE; MITOSIS INHIBITION; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN INDUCTION; TUMOR XENOGRAFT; ANIMAL; CELL CYCLE; CELL DIVISION; COLON TUMOR; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; FLOW CYTOMETRY; METABOLISM; NUDE MOUSE; PATHOLOGY; TUMOR CELL LINE; XENOGRAFT;

ANIMALS; BENZOTHIAZOLES; BENZOXAZOLES; CDC25 PHOSPHATASES; CELL CYCLE; CELL DIVISION; CELL LINE, TUMOR; COLONIC NEOPLASMS; CYCLIN-DEPENDENT KINASES; ENZYME INHIBITORS; FLOW CYTOMETRY; HUMANS; MICE; MICE, NUDE; QUINONES; TRANSPLANTATION, HETEROLOGOUS;

EID: 60549098655     PISSN: 00207136     EISSN: 10970215     Source Type: Journal    
DOI: 10.1002/ijc.24080     Document Type: Article

References (31)

1. Boutros R, Dozier C, Ducommun B. The when and wheres of CDC25 phosphatases. Curr Opin Cell Biol 2006;18:185-91.
2. Boutros R, Lobjois V, Ducommun B. CDC25 phosphatases in cancer cells: key players? Good targets? Nat Rev Cancer 2007;7:495-507.
3. Ma ZQ, Chua SS, DeMayo FJ, Tsai SY. Induction of mammary gland hyperplasia in transgenic mice over-expressing human cdc25B. Oncogene 1999;18:4564-76.
4. Yao Y, Slosberg ED, Wang L, Hibshoosh H, Zhang YJ, Xing WQ, Santella RM, Weinstein IB. Increased susceptibility to carcinogeninduced mammary tumors in MMTV- Cdc25B transgenic mice. Oncogene 1999;18:5159-66.
5. Ray D, Terao Y, Fuhrken PG, Ma ZQ, DeMayo FJ, Christov K, Heerema NA, Franks R, Tsai SY, Papoutsakis ET, Kiyokawa H. Deregulated CDC25A expression promotes mammary tumorigenesis with genomic instability. Cancer Res 2007;67:984-91.
6. Ray D, Terao Y, Nimbalkar D, Hirai H, Osmundson EC, Zou X, Franks R, Christov K, Kiyokawa H. Hemizygous disruption of Cdc25A inhibits cellular transformation and mammary tumorigenesis in mice. Cancer Res 2007;67:6605-11.
7. Kristjansdottir K, Rudolph J. Cdc25 phosphatases and cancer. Chem Biol 2004;11:1043-51.
8. Contour-Galcera MO, Sidhu A, Prevost G, Bigg D, Ducommun B. What's new on CDC25 phosphatase inhibitors. Pharmacol Ther 2007;115:1-12.
9. Lazo JS, Aslan DC, Southwick EC, Cooley KA, Ducruet AP, Joo B, Vogt A, Wipf P. Discovery and biological evaluation of a new family of potent inhibitors of the dual specificity protein phosphatase Cdc25. J Med Chem 2001;44:4042-9.
10. Brisson M, Foster C, Wipf P, Joo B, Tomko RJ, Jr, Nguyen T, Lazo JS. Independent mechanistic inhibition of cdc25 phosphatases by a natural product caulibugulone. Mol Pharmacol 2007;71:184-92.
11. Brisson M, Nguyen T, Vogt A, Yalowich J, Giorgianni AM, Tobi D, Bahar I, Stephenson CR, Wipf P, Lazo JS. Discovery and characterization of novel small molecule inhibitors of human Cdc25B dual specificity phosphatase. Mol Pharmacol 2004;66:824-33.
12. Brezak MC, Quaranta M, Mondesert O, Galcera MO, Lavergne O,Alby F, Cazales M, Baldin V, Thurieau C, Harnett J, Lanco C, Kasprzyk PG, et al. A novel synthetic inhibitor of CDC25 phosphatases: BN82002. Cancer Res 2004;64:3320-5.
13. Brezak MC, Quaranta M, Contour-Galcera MO, Lavergne O, Mondesert O, Auvray P, Kasprzyk PG, Prevost GP, Ducommun B. Inhibition of human tumor cell growth in vivo by an orally bioavailable inhibitor of CDC25 phosphatases. Mol Cancer Ther 2005;4: 1378-87.
14. Cao S, Foster C, Brisson M, Lazo JS, Kingston DG. Halenaquinone and xestoquinone derivatives, inhibitors of Cdc25B phosphatase from a Xestospongia sp. Bioorg Med Chem 2005;13:999-1003.
15. Contour-Galcera MO, Lavergne O, Brezak MC, Ducommun B, Prevost G. Synthesis of small molecule CDC25 phosphatases inhibitors. Bioorg Med Chem Lett 2004;14:5809-12.
16. Brun MP, Braud E, Angotti D, Mondesert O, Quaranta M, Montes M, Miteva M, Gresh N, Ducommun B, Garbay C. Design, synthesis, and biological evaluation of novel naphthoquinone derivatives with CDC25 phosphatase inhibitory activity. Bioorg Med Chem 2005;13: 4871-9.
17. Lazo JS, Nunes R, Skoko JJ, Queiroz de Oliveira PE, Vogt A, Wipf P. Novel benzofuran inhibitors of human mitogen-activated protein kinase phosphatase-1. Bioorg Med Chem 2006;14:5643-50.
18. Cossy J, Belotti D, Brisson M, Skoko JJ, Wipf P, Lazo JS. Biological evaluation of newly synthesized quinoline-5,8-quinones as Cdc25B inhibitors. Bioorg Med Chem 2006;14:6283-7.
19. Kar S, Wang M, Ham SW, Carr BI. H32, a non-quinone sulfone analog of vitamin K3, inhibits human hepatoma cell growth by inhibiting Cdc25 and activating ERK. Cancer Biol Ther 2006;5:1340-7.
20. Sohn J, Kiburz B, Li Z, Deng L, Safi A, Pirrung MC, Rudolph J. Inhibition of Cdc25 phosphatases by indolyldihydroxyquinones. J Med Chem 2003;46:2580-8.
21. Kim KR, Kwon JL, Kim JS, No Z, Kim HR, Cheon HG. EK-6136 (3- methyl-4-(O-methyl-oximino)-1-phenylpyrazolin-5-one): a novel Cdc25B inhibitor with antiproliferative activity. Eur J Pharmacol 2005;528:37-42.
22. Cheon HG, Kim SM, Yang SD, Ha JD, Choi JK. Discovery of a novel protein tyrosine phosphatase-1B inhibitor, KR61639: potential development as an antihyperglycemic agent. Eur J Pharmacol 2004;485: 333-9.
23. Cazales M, Boutros R, Brezak MC, Chaumeron S, Prevost G, Ducommun B. Pharmacologic inhibition of CDC25 phosphatases impairs interphase microtubule dynamics and mitotic spindle assembly. Mol Cancer Ther 2007;6:318-25.
24. Davezac N, Baldin V, Blot J, Ducommun B, Tassan JP. Human pEg3 kinase associates with and phosphorylates CDC25B phosphatase: a potential role for pEg3 in cell cycle regulation. Oncogene 2002;21: 7630-41.
25. Dutertre S, Cazales M, Quaranta M, Froment C, Trabut V, Dozier C, Mirey G, Bouche J, Theis-Febvre N, Schmitt E, Monsarrat B, Prigent C, et al. Phosphorylation of CDC25B by Aurora-A at the centrosome contributes to the G2/M transition. J Cell Sci 2004;117:2523-31.
26. Cazales M, Quaranta M, Lobjois V, Jullien D, Al Saati T, Delsol G, Ducommun B. A new mitotic-cell specific monoclonal antibody. Cell Cycle 2008;7:267-8.
27. Del Duca D, Werbowetski T, Del Maestro RF. Spheroid preparation from hanging drops: characterization of a model of brain tumor invasion. J Neurooncol 2004;67:295-303.
28. Lafon C, Mathieu C, Guerrin M, Pierre O, Vidal S, Valette A. Transforming growth factor beta 1-induced apoptosis in human ovarian carcinoma cells: protection by the antioxidant N-acetylcysteine and bcl-2. Cell Growth Differ 1996;7:1095-104.
29. Bugler B, Quaranta M, Aressy B, Brezak MC, Prevost G, Ducommun B. Genotoxic-activated G2-M checkpoint exit is dependent on CDC25B phosphatase expression. Mol Cancer Ther 2006;5:1446-51.
30. Theis-Febvre N, Filhol O, Froment C, Cazales M, Cochet C, Monsarrat B, Ducommun B, Baldin V. Protein kinase CK2 regulates CDC25B phosphatase activity. Oncogene 2003;22:220-32.
31. Beaupain R, Prevost G, Mainguene C, Laine-Bidron C, Tamboise A, Tamboise E. Continuous three-dimensional cultures of MCF-7 cells in serum free medium. In Vitro Cell Dev Biol Anim 1993;29A:893-8.