Dual-specificity phosphatase CDC25A/B inhibitor identified from a focused library with nonelectrophilic core structure

ACS Medicinal Chemistry Letters

Volumn 3, Issue 4, 2012, Pages 294-298

  Tsuchiya, Ayako ^a   Hirai, Go ^a   Koyama, Yusuke ^a   Oonuma, Kana ^a   Otani, Yuko ^a   Osada, Hiroyuki ^a   Sodeoka, Mikiko ^a,b  

^a RIKEN   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

CDC25; cell cycle; dual specificity protein phosphatases; focused library; inhibitor; reactive oxygen species

Indexed keywords

2 HYDROXYBENZYL DERIVATIVE; CYCLIN DEPENDENT KINASE 1; ENAMINE; PHOSPHATASE B; PHOSPHATASE CDC25A; PHOSPHOPROTEIN PHOSPHATASE; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR R344; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR RE12; QUINONE DERIVATIVE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ARTICLE; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CONCENTRATION (PARAMETERS); DEPHOSPHORYLATION; ELECTROPHILICITY; ENZYME INHIBITION; ENZYME SPECIFICITY; PRIORITY JOURNAL; PROTEIN ANALYSIS; SCREENING TEST; STRUCTURE ANALYSIS;

EID: 84859767484     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml2002778     Document Type: Article

References (22)

1. Malumbres, M.; Barbacid, M. Cell cycle, CDKs and cancer: a changing paradigm Nat. Rev. Cancer 2009, 9, 153-166
2. Boutros, R.; Lobjois, V.; Ducommun, B. CDC25 phosphatases in cancer cells: Key players? Good targets? Nat. Rev. Cancer 2007, 7, 495-507 (Pubitemid 46985396)
3. Kristjánsdóttir, K.; Rudolph, J. CDC25 phosphatases and cancer Chem. Biol. 2004, 11, 1043-1051 (Pubitemid 39138756)
4. Contour-Galcera, M. O.; Sidhu, A.; Prévost, G.; Bigg, D.; Ducommun, B. What's new on CDC25 phosphatase inhibitors Pharmacol. Ther. 2007, 115, 1-12 (Pubitemid 46990550)
5. Bialy, L.; Waldmann, H. Inhibitors of protein tyrosine phosphatases: Next-generation drugs? Angew. Chem., Int. Ed. 2005, 44, 3814-3839 (Pubitemid 40885689)
6. Lyon, M. A.; Ducruet, A. P.; Wipf, P.; Lazo, J. S. Dual-specificity phosphatases as targets for antineoplastic agents Nat. Rev. Drug Discovery 2002, 1, 961-976 (Pubitemid 37361602)
7. Lazo, J. S.; Aslan, D. C.; Southwick, E. C.; Cooley, K. A.; Ducruet, A. P.; 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, 4042-4049 (Pubitemid 33095313)
8. Lazo, J. S.; Nemoto, K.; Pestell, K. E.; Cooley, K.; Southwick, E. C.; Mitchell, D. A.; Furey, W.; Gussio, R.; Zaharevitz, D. W.; Joo, B.; Wipf, P. Identification of a potent and selective pharmacophore for CDC25 dual specificity phosphatase inhibitors Mol. Pharmacol. 2002, 61, 720-728 (Pubitemid 34273150)
9. Cao, S.; Foster, C.; Brisson, M.; Lazo, J. S.; Kingston, D. G. Halenaquinone and xestoquinone derivatives, inhibitors of CDC25B phosphatase from a Xestospongia sp Bioorg. Med. Chem. 2005, 13, 999-1003 (Pubitemid 40164583)
10. Brezak, M. C.; Valette, A.; Quaranta, M.; Contour-Galcera, M. O.; Jullien, D.; Lavergne, O.; Frongia, C.; Bigg, D.; Kasprzyk, P. G.; Prevost, G. P.; Ducommun, B. IRC-083864, a novel bis quinone inhibitor of CDC25 phosphatases active against human cancer cells Int. J. Cancer 2009, 124, 1449-1456
11. Pu, L.; Amoscato, A. A.; Bier, M. E.; Lazo, J. S. Dual G1 and G2 phase inhibition by a novel, selective CDC25 inhibitor 6-chloro-7-(2-morpholin-4- ylethylamino)quinoline-5,8-dione J. Biol. Chem. 2002, 277, 46877-46885 (Pubitemid 36159191)
12. Kar, S.; Lefterov, I. M.; Wang, M.; Lazo, J. S.; Scott, C. N.; Wilcox, C. S.; Carr, B. I. Binding and inhibition of CDC25 phosphatases by vitamin K analogues Biochemistry 2003, 42, 10490-10497 (Pubitemid 37071449)
13. Brisson, M.; Nguyen, T.; Wipf, P.; Joo, B.; Day, B. W.; Skoko, J. S.; Schreiber, E. M.; Foster, C.; Bansal, P.; Lazo, J. S. Redox regulation of CDC25B by cell-active quinolinediones Mol. Pharmacol. 2005, 68, 1810-1820 (Pubitemid 41656028)
14. Zhou, Y. B.; Feng, X.; Wang, L. N.; Du, J. Q.; Zhou, Y. Y.; Yu, H. P.; Zang, Y.; Li, J. Y.; Li, J. LGH00031, a novel ortho-quinonoid inhibitor of cell division cycle 25B, inhibits human cancer cells via ROS generation Acta Pharmacol. Sin. 2009, 30, 1359-1368
15. Buhrman, G.; Parker, B.; Sohn, J.; Rudolph, J.; Mattos, C. Structural mechanism of oxidative regulation of the phosphatase CDC25B via an intramolecular disulfide bond Biochemistry 2005, 44, 5307-5316 (Pubitemid 40489970)
16. 2 mediated cell signaling FEBS Lett. 2004, 560, 7-13 (Pubitemid 38264284)
17. Kar, S.; Wang, M.; Ham, S. W.; Carr, B. I. 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, 1340-1347 (Pubitemid 44772261)
18. Sodeoka, M.; Sampe, R.; Kojima, S.; Baba, Y.; Usui, T.; Ueda, K.; Osada, H. Synthesis of a tetronic acid library focused on inhibitors of tyrosine and dual-specificity protein phosphatases and its evaluation regarding VHR and CDC25B inhibition J. Med. Chem. 2001, 44, 3216-3222 (Pubitemid 32917101)
19. Hirai, G.; Tsuchiya, A.; Koyama, Y.; Otani, Y.; Oonuma, K.; Dodo, K.; Simizu, S.; Osada, H.; Sodeoka, M. Development of a Vaccinia H1-related (VHR) phosphatase inhibitor with a nonacidic phosphate-mimicking core structure ChemMedChem 2011, 6, 617-622
20. Rahmouni, S.; Cerignoli, F.; Alonso, A.; Tsutji, T.; Henkens, R.; Zhu, C.; Louis-dit-Sully, C.; Moutschen, M.; Jiang, W.; Mustelin, T. Loss of the VHR dual-specific phosphatase causes cell-cycle arrest and senescence Nat. Cell Biol. 2006, 8, 524-531
21. Mineo, C.; Murakami, Y.; Ishimi, Y.; Hanaoka, F.; Yamada, M. Isolation and analysis of a mammalian temperature-sensitive mutant defective in G2 functions Exp. Cell Res. 1986, 167, 53-62 (Pubitemid 17178183)
22. Th'ng, J. P. H; Wright, P. S.; Hamaguchi, J.; Lee, M. G.; Norbury, C. J.; Nurse, P.; Bradbury, E. M. The FT210 cell line is a mouse G2 phase mutant with a temperature-sensitive CDC2 gene product Cell 1990, 63, 313-324