Identification of the spiro(oxindole-3,3′-thiazolidine)-based derivatives as potential p53 activity modulators

Journal of Medicinal Chemistry

Volumn 53, Issue 23, 2010, Pages 8319-8329

  Gomez Monterrey, Isabel ^a   Bertamino, Alessia ^a   Porta, Amalia ^b   Carotenuto, Alfonso ^a   Musella, Simona ^b   Aquino, Claudio ^a   Granata, Ilaria ^b   Sala, Marina ^b   Brancaccio, Diego ^a   Picone, Delia ^a   Ercole, Carmine ^a   Stiuso, Paola ^c   Campiglia, Pietro ^b   Grieco, Paolo ^a   Ianelli, Pio ^b   Maresca, Bruno ^b   Novellino, Ettore ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF SALERNO   (Italy)

^c SECOND UNIVERSITY OF NAPLES   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

(3,7A) 5' METHYL 6 (3,4,5 TRIMETHOXYBENZYL) 1H SPIRO[IMIDAZO[1,5 C]THIAZOLE 3,3' INDOLINE] 2',5,7 (6H,7AH)TRIONE; (3,7A) 6 (4 CHLOROBENZYL) 1H SPIRO[IMIDAZO[1,5 C]THIAZOLE 3,3' INDOLINE] 2',5,7 (6H,7AH)TRIONE; ANTINEOPLASTIC AGENT; PROTEIN MDM2; PROTEIN P53; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CANCER INHIBITION; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL CYCLE PROGRESSION; CONTROLLED STUDY; DRUG DESIGN; DRUG IDENTIFICATION; GROWTH INHIBITION; HUMAN; HUMAN CELL; MELANOMA CELL; TUMOR CELL LINE; TUMOR GROWTH;

APOPTOSIS; CELL LINE; CELL LINE, TUMOR; FLOW CYTOMETRY; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; PROTO-ONCOGENE PROTEINS C-MDM2; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; THIAZOLIDINES; TUMOR SUPPRESSOR PROTEIN P53;

EID: 78649825828     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100838z     Document Type: Article

References (42)

1. Vogelstein, B.; Lane, D.; Levine, A. J. Surfing the p53 Network Nature 2000, 408, 307-310
2. Vousden, K. H.; Lu, X. Live or Let Die: The Cell's Response to p53 Nat. Rev. Cancer 2002, 2, 594-604
3. Levine, A. J. P53, The Cellular Gatekeeper for Growth and Division Cell 1997, 88, 323-331
4. Hainaut, P.; Hollstein, M. P53 and Human Cancer: The First Ten Thousand Mutations Adv. Cancer Res. 2000, 77, 81-137
5. Olivier, M.; Eeles, R.; Hollstein, M.; Khan, M. A.; Harris, C. C.; Hainaut, P. The IARC TP53 Database: New Online Mutation Analysis and Recommendations to Users Hum. Mutat. 2002, 19, 607-614
6. Freedman, D. A.; Wu, L.; Levine, A. J. Functions of the MDM2 Oncoprotein Cell. Mol. Life Sci. 1999, 55, 96-107
7. Momand, J.; Wu, H. H.; Dasgupta, G. MDM2 Master Regulator of the p53 Tumor Suppressor Protein Gene 2000, 242, 15-29
8. Haupt, Y.; Maya, R.; Kazaz, A.; Moshe, O. Mdm2 Promotes the Rapid Degradation of p53 Nature 1997, 387, 296-299
9. Kubbutat, M. H. G.; Jones, S. N.; Vousden, K. H. Regulation of p53 Stability by Mdm2 Nature 1997, 387, 299-303
10. Juven-Gershon, T.; Oren, M. Mdm2: The Ups and Downs Mol. Med. 1999, 5, 71-83
11. Fakharzadeh, S. S.; Trusko, S. P.; George, D. L. Tumorigenic Potential Associated with Enhanced Expression of a Gene That Is Amplified in a Mouse Tumor Cell Line EMBO J. 1991, 10, 1565-1569
12. Oliner, J. D.; Kinzler, K. W.; Meltzer, P. S.; George, D. L.; Vogelstein, B. Amplification of a Gene Encoding a p53-Associated Protein in Human Sarcomas Nature 1992, 358, 80-83
13. Bottger, A.; Bottger, V.; Sparks, A.; Liu, W. L.; Howard, S. F.; Lane, D. P. Design of a Synthetic Mdm2-Binding Mini Protein that Activates the p53 Response in Vivo Curr. Biol. 1997, 7, 860-869
14. Chen, L.; Lu, W.; Agrawal, S.; Zhou, W.; Zhang, R.; Chen, J. Ubiquitous Induction of p53 in Tumor Cells by Antisense Inhibition of MDM2 Expression Mol. Med. 1999, 5, 21-34
15. Zhang, Z.; Li, M.; Wang, H.; Agrawal, S.; Zhang, R. Antisense Therapy Targeting MDM2 Oncogene in Prostate Cancer: Effects on Proliferation, Apoptosis, Multiple Gene Expression, and Chemotherapy Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 11636-11641
16. Wang, H.; Nan, L.; Yu, D.; Agrawal, S.; Zhang, R. Antisense Anti-MDM2 Oligonucleotides as a Novel Therapeutic Approach to Human Breast Cancer: In Vitro and in Vivo Activities and Mechanisms Clin. Cancer Res. 2001, 7, 3613-3624
17. Wasylyk, C.; Salvi, R.; Argentini, M.; Dureuil, C.; Delumeau, I.; Abecassis, J.; Debussche, L.; Wasylyk, B. P53 Mediated Death of Cells Overexpressing MDM2 by an Inhibitor of MDM2 Interaction with p53 Oncogene 1999, 18, 1921-1934
18. Chene, P.; Fuchs, J.; Carena, I.; Furet, P.; Garcia-Echeverria, C. Study of the Cytotoxic Effect of a Peptidic Inhibitor of the p53-Hdm2 Interaction in Tumor Cells FEBS Lett. 2002, 529, 293-297
19. Klein, C.; Vassilev, L. T. Targeting the p53-MDM2 Interaction to Treat Cancer Br. J. Cancer 2004, 91, 1415
20. Vassilev, L. T. p53 Activation by Small Molecules: Application in Oncology J. Med. Chem. 2005, 48, 4491-4499
21. Chen, J.; Marechal, V.; Levine, A. J. Mapping of the p53 and Mdm-2 Interaction Domains Mol. Cell. Biol. 1993, 13, 4107-4114
22. Kussie, P. H.; Gorina, S.; Marechal, V.; Elenbaas, B.; Moreau, J.; Levine, A. J.; Pavletich, N. P. Structure of the MDM2 Oncoprotein Bound to the p53 Tumor Suppressor Transactivation Domain Science 1996, 274, 948-953 (Pubitemid 26398409)
23. Murray, J. K.; Gellman, S. H. Targeting Protein-Protein Interactions: Lessons from p53/MDM2 Biopolymers 2007, 88, 657-686
24. Shangary, S.; Wang, S. Small-Molecule Inhibitors of the MDM2-p53 Protein-Protein Interaction to Reactivate p53 Function: A Novel Approach for Cancer Therapy Annu. Rev. Pharmacol. Toxicol. 2009, 49, 223-241
25. Zhao, J.; Wang, M.; Chen, J.; Luo, A.; Wanga, X.; Wua, M.; Yinb, D.; Liua, Z. The Initial Evaluation of Non-Peptidic Small-Molecule HDM2 Inhibitors Based on p53-HDM2 Complex Structure Cancer Lett. 2002, 183, 69-77
26. Galatin, P. S.; Abraham, D. J. A Nonpeptidic Sulfonamide Inhibits the p53-mdm2 Interaction and Activates p53-Dependent Transcription in Mdm2-Overexpressing Cells J. Med. Chem. 2004, 47, 4163-4165
27. Grasberger, B. L.; Lu, T.; Schubert, C.; Parks, D. J.; Carver, T. E.; Koblish, H. K.; Cummings, M. D.; LaFrance, L. V.; Milkiewicz, K. L.; Calvo, R. R.; Maguire, D.; Lattanze, J.; Franks, C. F.; Zhao, S.; Ramachandren, K.; Bylebyl, G. R.; Zhang, M.; Manthey, C. L.; Petrella, E. C.; Pantoliano, M. W.; Deckman, I. C.; Spurlino, J. C.; Maroney, A. C.; Tomczuk, B. E.; Molloy, C. J.; Bone, R. F. Discovery and Cocrystal Structure of Benzodiazepinedione HDM2 Antagonists That Activate p53 in Cells J. Med. Chem. 2005, 48, 909-912
28. Vassilev, L. T.; Vu, B. T.; Graves, B.; Carvajal, D.; Podlaski, F.; Filipovic, Z.; Kong, N.; Kammlott, U.; Lukacs, C.; Klein, C.; Fotouhi, N.; Liu, E. A. In Vivo Activation of the p53 Pathway by Small-Molecule Antagonists of MDM2 Science 2004, 303, 844-848
29. Ding, K.; Lu, Y.; Nikolovska-Coleska, Z.; Qui, S.; Ding, Y.; Gao, W.; Stuckey, J.; Krajewski, K.; Roller, P. P.; Tomita, Y.; Parrish, D. A.; Deschamps, J. R.; Wang, S. Structure-Based Design of Potent Non-Peptide MDM2 Inhibitors J. Am. Chem. Soc. 2005, 127, 10130-10131
30. Yu, S.; Qin, D.; Shangary, S.; Chen, J.; Wang, G.; Ding, K.; McEachern, D.; Qiu, S.; Nikolovska-Coleska, Z.; Miller, R.; Kang, S.; Yang, D.; Wang, S. Potent and Orally Active Small-Molecule Inhibitors of the MDM2-p53 Interaction J. Med. Chem. 2009, 52, 7970-7973
31. Issaeva, N.; Bozko, P.; Enge, M.; Protopopova, M.; Verhoef, L. G. G. C.; Masucci, M.; Pramanik, A.; Selivanova, G. Small Molecule RITA Binds to p53, Blocks p53-HDM-2 Interaction and Activates p53 Function in Tumors Nat. Med. 2004, 10, 1321-1328
32. Galliford, C. V.; Scheidt, K. A. Pyrrolidinyl-Spirooxindole Natural Products as Inspirations for the Development of Potential Therapeutic Agents Angew. Chem., Int. Ed. 2007, 46, 8748-8758
33. Bertamino, A.; Aquino, C.; Sala, M.; de Simone, N.; Mattia, C. A.; Erra, L.; Musella, S.; Iannelli, P.; Carotenuto, A.; Grieco, P.; Novellino, E.; Campiglia, P.; Gomez- Monterrey, I. Design and Synthesis of Spirotryprostatin- Inspired Diketopiperazine Systems from Prolyl Spirooxoindolethiazolidine Derivatives Bioorg. Med. Chem. 2010, 18, 4328-4337
34. Dömling, A. Small Molecular Weight Protein-Protein Interaction Antagonists-An Insurmountable Challenge? Curr. Opin. Chem. Biol. 2008, 12, 281-291
35. Miskolczi, I.; Zekany, A.; Rantal, F.; Linden, A.; Kover, K.; Gyorgydeak, Z. Diastereo- and Regioisomeric Bicyclic Thiohydantoins from Chiral 1,3-Thiazolidine-2,4-Dicarboxylic Acids Helv. Chim. Acta 1998, 81, 744-753
36. Kerr, J. F. R.; Wyllie, A. H.; Currie, A. R. Apoptosis: A Basic Biological Phenomenon with Wide-Ranging Implications in Tissue Kinetics Br. J. Cancer 1972, 26, 239-257
37. Jaanicke, R. U.; Sprengart, M. L.; Wati, M. R.; Porter, A. G. Caspase-3 Is Required for DNA Fragmentation and Morphological Changes Associated with Apoptosis J. Biol. Chem. 1998, 273, 9357-9360
38. Germain, M.; Affar, E. B.; D'Amours, D.; Dixit, V. M.; Salvesen, G. S.; Poirier, G. G. Cleavage of Automodified Poly(ADP-ribose) Polymerase During Apoptosis J. Biol. Chem. 1999, 274, 28379-28384
39. D'Silva, L.; Ozdowy, P.; Krajewski, M.; Rothweiler, U.; Singh, M.; Holak, T. A. Monitoring the Effects of Antagonists on Protein-Protein Interactions with NMR Spectroscopy J. Am. Chem. Soc. 2005, 127, 13220-13226
40. Krajewski, M.; Rothweiler, U.; D'Silva, L.; Sudipta Majumdar, S.; Klein, C.; Holak., T. A. An NMR-Based Antagonist Induced Dissociation Assay for Targeting the Ligand-Protein and Protein-Protein Interactions in Competition Binding Experiments J. Med. Chem. 2007, 50, 4382-4387
41. Dawson, R.; Mueller, L.; Dehner, A.; Klein, C.; Kessler, H.; Buchner, J. The N-terminal Domain of p53 Is Natively Unfolded J. Mol. Biol. 2003, 332, 1131-1141
42. Hwang, T. L.; Shaka, A. J. Water Suppression That Works. Excitation Sculpting Using Arbitrary Wave-Forms and Pulsed-Field Gradients J. Magn. Reson. 1995, 112, 275-279