Small molecule inhibitors of the XIAP protein-protein interaction

Current Topics in Medicinal Chemistry

Volumn 7, Issue 10, 2007, Pages 966-971

  Rajapakse, Hemaka A ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Apoptosis; BIR 2; BIR 3; Smac; Small molecule inhibitor; XIAP

Indexed keywords

4 (4 BROMOPHENYL) 5 PHENYLAMINOTHIAZOLE; 4 METHYL 5 PHENYLAMINOTHIAZOLE; ANTINEOPLASTIC AGENT; ANTISENSE OLIGONUCLEOTIDE; CARBANILAMIDE DERIVATIVE; CASPASE 3; CASPASE 7; CASPASE 9; DOXORUBICIN; EMBELIN; ETOPOSIDE; PACLITAXEL; PEPTIDE DERIVATIVE; PROTEIN BAX; SECOND MITOCHONDRIAL ACTIVATOR OF CASPASE; SMALL INTERFERING RNA; SULFONAMIDE; TETRAZOLE DERIVATIVE; THIAZOLE DERIVATIVE; TWX 006; TWX 024; UBIQUITIN PROTEIN LIGASE E3; UNCLASSIFIED DRUG; X LINKED INHIBITOR OF APOPTOSIS;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; BREAST CANCER; CANCER INHIBITION; CELL DEATH; CELL PROLIFERATION; CLINICAL TRIAL; COMPLEX FORMATION; DRUG DESIGN; DRUG EFFICACY; DRUG IDENTIFICATION; DRUG POTENCY; DRUG POTENTIATION; DRUG SCREENING; DRUG SENSITIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ACTIVE SITE; HUMAN; IC 50; NONHUMAN; PROGNOSIS; PROTEIN DOMAIN; PROTEIN FUNCTION; PROTEIN PROTEIN INTERACTION; PROTEIN STRUCTURE; REVIEW; SIGNAL TRANSDUCTION; SOLID PHASE SYNTHESIS; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CASPASES; DRUG DESIGN; HUMANS; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; PROTEIN BINDING; PROTEIN INTERACTION MAPPING; X-LINKED INHIBITOR OF APOPTOSIS PROTEIN;

EID: 34447255680     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802607780906816     Document Type: Review

References (26)

1. Hanahan, D.; Weinberg, R. A. The hallmarks of cancer. Cell 2000, 100, 57-70.
2. Lowe, S. W.; Cepero, E.; Evan, G. Intrinsic tumor suppression. Nature 2004, 432, 307-315.
3. Arkin, M. Protein-protein interactions and cancer: small molecules going in for the kill. Curr. Opinion Chem. Biol. 2005, 9, 317-324.
4. Deveraux, Q. L.; Takahashi, R.; Salvesen, G. S.; Reed, J. C. X-linked IAP is a direct inhibitor of cell death proteases. Nature 1997, 388, 300-304.
5. Salvesen, G. S.; Duckett, C. S. IAP proteins: blocking the road to death's door. Nat. Rev. Mol. Cell Biol. 2002, 3, 401-410.
6. Wrzesien-Kus, A.; Smolewski, P.; Sobczak-Pluta, A.; Wierzbowska, A.; Robak, T. The inhibitor of apoptosis family and it antagonists in acute leukemias. Apoptosis 2004, 9, 705-715.
7. Shi, Y. Caspase activation, inhibition and reactivation: a mechanistic view. Protein Sci. 2004, 13, 1979-1987.
8. Schimmer, A. D.; Dalili, S.; Batey, R. A.; Riedl, S. J. Targeting XIAP for the treatment of malignancy. Cell Death Differ. 2006, 13, 179-188.
9. Deveraux, Q. L.; Roy, N.; Stennicke, H. R.; Welsh, K.; Salvesen, G. S.; Reed. J. C. Cleavage of human apoptosis protein XIAP results in fragments with distinct specificities for caspases. EMBO J. 1999, 18, 5242-5251.
10. Sun, C.; Cai, M.; Meadows, R. P.; Xu, N.; Gunasekara, A. H.; Hermann, J.; Wu, J. C.; Fesik, S. W. NMR structure and mutagenesis of the third Bir domain of the inhibitor of apoptosis protein XIAP. J. Biol. Chem. 2000, 275, 33777-33781.
11. Tamm, I.; Richter, S.; Scholz, F.; Schmelz, K.; Oltersdorf, D.; Karawajew, L.; Schoch, C.; Haferlach, T.; Ludwig, W. D.; Wuchter, C. XIAP expression correlates with monocytic differentiation in aduct de novo AML: impact on prognosis. Hematol J. 2004, 89, 489-495.
12. Tamm, I.; Richter, S.; Oltersdorf, D.; Creutzig, U.; Harbott, J.; Scholz, F.; Karawajew, L.; Ludwig, W. D.; Wuchter, C. High expression levels of X-linked inhibitor of apoptosis protein and survivin correlate with poor overall survival in childhood de novo acute myeloid leukemia. Clin. Cancer Res. 2004, 10, 3737-3744.
13. Carter, B. Z.; Kornblau, S. M.; Tsao, T.; Wang, R. Y.; Schober, W. D.; Milella, M.; Sung, H. G.; Reed, J. C.; Andreef, M. Caspase-independent cell death in AML: caspase inhibition in vivo with pan-caspase inhibitors or in vivo by XIAP or survivin does not affect cell survival or prognosis. Blood 2003, 102, 4179-4186.
14. Ferreira, C. G.; van der Valk, P.; Span, S. W.; Ludwig, I.; Smit, E. F.; Kruyt, F. A.; Pinedo, H. M.; van Tinteren, H.; Giaccone, G. Expression of x-linked inhibitor of apoptosis as a novel prognostic marker in radically resected non-small cell cancer patients. Clin. Cancer Res. 2001, 7, 2468-2474.
15. See www.aegera.com.
16. Wu, T. Y. H.; Wagner, K. W.; Bursulaya, B.; Schultz, P. G.; Deveraux, Q. L. Development and characterization of nonpeptidic small molecule inhibitors of the XIAP/caspase-3 interaction. Chem. Biol. 2003, 10, 759-767.
17. Shimmer, A. D.; Welsh, K.; Pinilla, C.; Wang, Z.; Krajewska, M.; Bonneau, M.-J.; Pedersen, I. M.; Kitada, S.; Scott, F. L.; Bailly-Maitre, B.; Glinsky, G.; Scudiero, D.; Sausville, E.; Salvesen, G.; Nefzi, A.; Ostresh, J. M.; Houghten, R. A.; Reed, J. C. Small-molecule antagonists of apoptosis suppressor XIAP exhibit broad antitumor activity. Cancer Cell 2004, 5, 25-35.
18. Sun, H.; Nikolovska-Coleska, Z.; Yang, C.-Y.; Xu, L.; Tomita, Y.; Krajewski, K.; Roller, P. P.; Wang, S. Structure-based design, synthesis and evaluation of conformationally constrained mimetics of the second mitochondria-derived activator of caspase that target the X-linked inhibitor of apoptosis protein/caspase-9 interaction site. J. Med. Chem. 2004, 47, 4147-4150.
19. Sun, H.; Nikolovska-Coleska, Z.; Chen, J.; Yang, C.-Y.; Tomita, Y.; Pan, H.; Yoshioka, Y.; Krajewski, K.; Roller, P. P.; Wang, S. Structure-based design, synthesis and biochemical testing of novel and potent Smac peptidomimetics, Bioorg. Med. Chem. Lett. 2005, 15, 793-797.
20. Sun, H.; Nikolovska-Coleska, Z.; Yang, C.-Y.; Xu, L.; Liu, M.; Tomita, Y.; Pan, H.; Yoshioka, Y.; Krajewski, K.; Roller, P. P.; Wang, S. Structure-based design of potent conformationally constrained Smac mimetics. J. Am. Chem. Soc. 2004, 126, 16686-16687.
21. Oost, T. K.; Sun. C.; Armstrong, R. C.; Al-Assaad, A.-S.; Betz, S. F.; Deckwerth, T. L.; Ding, H.; Elmore, S. W.; Meadows, R. P.; Olejnicznak, E. T.; Oleksijew, A.; Oltersdorf, T.; Rosenberg, S. H.; Shoemaker, A. R.; Tomaselli, K. J.; Zou, H.; Fesik, S. W. J. Med. Chem. 2004, 47, 4417-4426.
22. Zobel, K.; Wang, L.; Varfolomeev, E.; Franklin, M. C.; Elliot, L. O.; Wallweber, H. J. A.; Okawa, D. C.; Flygare, J. A.; Vucic, D.; Fairbrother, W. J.; Deshayes, K. Design, synthesis, and biological activity of a potent Smac mimetic that sensitizes cancer cells to apoptosis by antagonizing IAP's. ACS Chem. Biol. 2006, 1, 525-533.
23. Nikolovska-Coleska, Z.; Xu, L.; Hu, Z.; Tomita, Y.; Li, P.; Roller, P. P.; Wang, R.; Fang, X.; Guo, R.; Zhang, M.; Lippman, M. E.; Yang, D.; Wang, S. Discovery of embelin as a cell-permeable, small-molecular weight inhibitor of XIAP through structure-based computational screening of a traditional herbal medicine three-dimensional structure databse. J. Med. Chem. 2004, 47, 2430-2440.
24. Chen, J.; Nikolovska-Coleska, Z.; Wang, G.; Qiu, S.; Wang, S. Design, synthesis and characterization of new embelin derivatives as potent inhibitors of X-linked inhibitor of apoptosis protein. Bioorg. Med. Chem. Lett. 2006, 16, 5805-5808.
25. Li, L.; Thomas, R. M.; Suzuki, H.; De Brabander, J. K.; Wang, X.; Harran, P. G. A small molecule Smac mimic potentiates TRAIL- and TNFa-mediated cell death. Science 2004, 305, 1471-1474.
26. Park, C.-M.; Sun, C.; Olejniczak, E. T.; Wilson, A. E.; Meadows, R. P.; Betz, S. F.; Elmore, S. W.; Fesik, S. W. Non-peptidic small molecule inhibitors of XIAP. Bioorg. Med. Chem. Lett. 2005, 15, 771-775.