Molecular Oncology
Volume 2, Issue 1 , Pages 70-80 , June 2008

Mutant p53 targeting by the low molecular weight compound STIMA-1

  • Nicole Zache

      Affiliations

    • Karolinska Institutet, Department of Oncology-Pathology, Cancer Center Karolinska (CCK), Karolinska University Hospital, Stockholm, Sweden
  • ,
  • Jeremy M.R. Lambert

      Affiliations

    • Karolinska Institutet, Department of Oncology-Pathology, Cancer Center Karolinska (CCK), Karolinska University Hospital, Stockholm, Sweden
    • International Agency for Research on Cancer (IARC), World Health Organization, Lyon, France
  • ,
  • Nina Rökaeus

      Affiliations

    • Karolinska Institutet, Department of Oncology-Pathology, Cancer Center Karolinska (CCK), Karolinska University Hospital, Stockholm, Sweden
  • ,
  • Jinfeng Shen

      Affiliations

    • Karolinska Institutet, Department of Oncology-Pathology, Cancer Center Karolinska (CCK), Karolinska University Hospital, Stockholm, Sweden
  • ,
  • Pierre Hainaut

      Affiliations

    • International Agency for Research on Cancer (IARC), World Health Organization, Lyon, France
  • ,
  • Jan Bergman

      Affiliations

    • Karolinska Institutet, Department of Biosciences, Novum, Huddinge, Sweden
  • ,
  • Klas G. Wiman

      Affiliations

    • Karolinska Institutet, Department of Oncology-Pathology, Cancer Center Karolinska (CCK), Karolinska University Hospital, Stockholm, Sweden
    • Corresponding Author InformationCorresponding author. Cancer Center Karolinska (CCK), R8:04, Karolinska University Hospital, 171 76 Stockholm, Sweden. Tel.: +48 8 5177 9342; fax: +46 8 321 047.
  • ,
  • Vladimir J.N. Bykov

      Affiliations

    • Karolinska Institutet, Department of Oncology-Pathology, Cancer Center Karolinska (CCK), Karolinska University Hospital, Stockholm, Sweden

Received 28 October 2007 ,Revised 25 February 2008 ,Accepted 28 February 2008.

References 

  1. Bhanoori M, Yellaturu CR, Ghosh SK, Hassid A, Jennings LK, Rao GN. Thiol alkylation inhibits the mitogenic effects of platelet-derived growth factor and renders it proapoptotic via activation of STATs and p53 and induction of expression of caspase1 and p21(waf1/cip1). Oncogene. 2003;22:117–130
  2. Bogert MT, Beal GD, et al. Researches on quinazolones. XXVI. Synthesis of some stilbazoles, hydrazones and Schiff bases in the 4-quinazolone group. J. Am. Chem. Soc. 1911;32:1654–1664
  3. Borresen-Dale AL. TP53 and breast cancer. Hum. Mutat. 2003;21:292–300
  4. Bykov VJ, Issaeva N, Selivanova G, Wiman KG. Mutant p53-dependent growth suppression distinguishes PRIMA-1 from known anticancer drugs: a statistical analysis of information in the National Cancer Institute database. Carcinogenesis. 2002;23:2011–2018
  5. Bykov VJ, Issaeva N, Shilov A, Hultcrantz M, Pugacheva E, Chumakov P, et al. Restoration of the tumor suppressor function to mutant p53 by a low-molecular-weight compound. Nat. Med. 2002;8:282–288
  6. Bykov VJ, Selivanova G, Wiman KG. Small molecules that reactivate mutant p53. Eur. J. Cancer. 2003;39:1828–1834
  7. Bykov VJ, Issaeva N, Zache N, Shilov A, Hultcrantz M, Bergman J, et al. Reactivation of mutant p53 and induction of apoptosis in human tumor cells by maleimide analogs. J. Biol. Chem. 2005;280:30384–30391
  8. Bykov VJ, Zache N, Stridh H, Westman J, Bergman J, Selivanova G, et al. PRIMA-1(MET) synergizes with cisplatin to induce tumor cell apoptosis. Oncogene. 2005;24:3484–3491
  9. Campling BG, El-Deiry WS. Clinical implications of p53 mutations in lung cancer. Methods Mol. Med. 2003;75:53–77
  10. Dorr RT, Von Hoff DD. Cancer Chemotherapy Handbook. second ed.. Norwalk, CT: Appleton and Lange; 1994;
  11. El-Deiry WS. Regulation of p53 downstream genes. Semin. Cancer Biol. 1998;8:345–357
  12. Foster BA, Coffey HA, Morin MJ, Rastinejad F. Pharmacological rescue of mutant p53 conformation and function. Science. 1999;286:2507–2510
  13. Friedler A, Hansson LO, Veprintsev DB, Freund SM, Rippin TM, Nikolova PV, et al. A peptide that binds and stabilizes p53 core domain: chaperone strategy for rescue of oncogenic mutants. Proc. Natl. Acad. Sci. U.S.A. 2002;99:937–942
  14. Greenblatt MS, Bennett WP, Hollstein M, Harris CC. Mutations in the p53 tumor suppressor gene: clues to cancer etiology and molecular pathogenesis. Cancer Res. 1994;54:4855–4878
  15. Hainaut P, Hollstein M. p53 and human cancer: the first ten thousand mutations. Adv. Cancer Res. 2000;77:81–137
  16. Hainaut P, Milner J. Redox modulation of p53 conformation and sequence-specific DNA binding in vitro. Cancer Res. 1993;53:4469–4473
  17. Jiang JB, Hesson DP, Dusak BA, Dexter DL, Kang GJ, Hamel E. Synthesis and biological evaluation of 2-styrylquinazolin-4(3H)-ones, a new class of antimitotic anticancer agents which inhibit tubulin polymerization. J. Med. Chem. 1990;33:1721–1728
  18. Kelland LR, Farrell NP. Platinum-based Drugs in Cancer Therapy. Totowa, NJ: Humana Press; 2000;
  19. Levine AJ. p53, the cellular gatekeeper for growth and division. Cell. 1997;88:323–331
  20. Luu Y, Bush J, Cheung KJ, Li G. The p53 stabilizing compound CP-31398 induces apoptosis by activating the intrinsic Bax/mitochondrial/caspase-9 pathway. Exp. Cell Res. 2002;276:214–222
  21. Matas D, Sigal A, Stambolsky P, Milyavsky M, Weisz L, Schwartz D, et al. Integrity of the N-terminal transcription domain of p53 is required for mutant p53 interference with drug-induced apoptosis. Embo J. 2001;20:4163–4172
  22. North S, Pluquet O, Maurici D, El-Ghissassi F, Hainaut P. Restoration of wild-type conformation and activity of a temperature-sensitive mutant of p53 (p53(V272M)) by the cytoprotective aminothiol WR1065 in the esophageal cancer cell line TE-1. Mol. Carcinog. 2002;33:181–188
  23. Ohnishi T, Matsumoto H, Wang X, Takahashi A, Tamamoto T, Ohnishi K. Restoration by glycerol of p53-dependent apoptosis in cells bearing the mutant p53 gene. Int. J. Radiat. Biol. 1999;75:1095–1098
  24. Olivier M, Eeles R, Hollstein M, Khan MA, Harris CC, Hainaut P. The IARC TP53 database: new online mutation analysis and recommendations to users. Hum. Mutat. 2002;19:607–614
  25. Rainwater R, Parks D, Anderson ME, Tegtmeyer P, Mann K. Role of cysteine residues in regulation of p53 function. Mol. Cell. Biol. 1995;15:3892–3903
  26. Rippin TM, Bykov VJ, Freund SM, Selivanova G, Wiman KG, Fersht AR. Characterization of the p53-rescue drug CP-31398 in vitro and in living cells. Oncogene. 2002;21:2119–2129
  27. Ryan KM, Phillips AC, Vousden KH. Regulation and function of the p53 tumor suppressor protein. Curr. Opin. Cell Biol. 2001;13:332–337
  28. Samuels-Lev Y, O'Connor DJ, Bergamaschi D, Trigiante G, Hsieh JK, Zhong S, et al. ASPP proteins specifically stimulate the apoptotic function of p53. Mol. Cell. 2001;8:781–794
  29. Selivanova G, Iotsova V, Okan I, Fritsche M, Strom M, Groner B, et al. Restoration of the growth suppression function of mutant p53 by a synthetic peptide derived from the p53 C-terminal domain. Nat. Med. 1997;3:632–638
  30. Seo YR, Kelley MR, Smith ML. Selenomethionine regulation of p53 by a ref1-dependent redox mechanism. Proc. Natl. Acad. Sci. U.S.A. 2002;99:14548–14553
  31. Shi LM, Fan Y, Myers TG, O'Connor PM, Paull KD, Friend SH, et al. Mining the NCI anticancer drug discovery databases: genetic function approximation for the QSAR study of anticancer ellipticine analogues. J. Chem. Inf. Comput. Sci. 1998;38:189–199
  32. Smith MA, March J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. New York: John Wiley & Sons; 2001;
  33. Sun XZ, Vinci C, Makmura L, Han S, Tran D, Nguyen J, et al. Formation of disulfide bond in p53 correlates with inhibition of DNA binding and tetramerization. Antioxid. Redox Signal. 2003;5:655–665
  34. Takimoto R, Wang W, Dicker DT, Rastinejad F, Lyssikatos J, El-Deiry WS. The mutant p53-conformation modifying drug, CP-31398, can induce apoptosis of human cancer cells and can stabilize wild-type p53 protein. Cancer Biol. Ther. 2002;1:47–55
  35. Vogelstein B, Lane D, Levine AJ. Surfing the p53 network. Nature. 2000;408:307–310
  36. Wang W, Takimoto R, Rastinejad F, El-Deiry WS. Stabilization of p53 by CP-31398 inhibits ubiquitination without altering phosphorylation at serine 15 or 20 or MDM2 binding. Mol. Cell. Biol. 2003;23:2171–2181
  37. Wischhusen J, Naumann U, Ohgaki H, Rastinejad F, Weller M. CP-31398, a novel p53-stabilizing agent, induces p53-dependent and p53-independent glioma cell death. Oncogene. 2003;22:8233–8245
  38. Witt A, Bergman J. Synthesis and reactions of some 2-Vinyl-3H-quinazolin-4-ones. Tetrahedron. 2000;56:7245–7253
  39. Witt A, Bergman J. Total syntheses of the benzodiazepine alkaloids circumdatin F and circumdatin C. J. Org. Chem. 2001;66:2784–2788

PII: S1574-7891(08)00028-8

doi: 10.1016/j.molonc.2008.02.004

Molecular Oncology
Volume 2, Issue 1 , Pages 70-80 , June 2008