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

Journal of Medicinal Chemistry

Volumn 47, Issue 17, 2004, Pages 4147-4150

  Sun, Haiying ^a   Nikolovska Coleska, Zaneta ^a   Yang, Chao Yie ^a   Xu, Liang ^a   Tomita, York ^b   Krajewski, Krzysztof ^c   Roller, Peter P ^c   Wang, Shaomeng ^a  

^a UNIVERSITY OF MICHIGAN COMPREHENSIVE CANCER CENTER   (United States)

^b GEORGETOWN UNIVERSITY   (United States)

^c NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALANYLVALYLPROLYLISOLEUCINE; CASPASE 9; CISPLATIN; PEPTIDE; PEPTIDE DERIVATIVE; SECOND MITOCHONDRIAL ACTIVATOR OF CASPASE; UNCLASSIFIED DRUG; X LINKED INHIBITOR OF APOPTOSIS;

APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL DEATH; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG DESIGN; DRUG POTENCY; DRUG TARGETING; ENZYME ACTIVATION; HUMAN; HUMAN CELL; PROSTATE CANCER; PROTEIN DOMAIN; PROTEIN PROTEIN INTERACTION; STRUCTURE ANALYSIS; TARGET CELL;

AMINO ACID MOTIFS; APOPTOSIS; CARRIER PROTEINS; CASPASE 9; CASPASES; CELL LINE, TUMOR; CYCLIZATION; HETEROCYCLIC COMPOUNDS, 2-RING; HUMANS; INTRACELLULAR SIGNALING PEPTIDES AND PROTEINS; MITOCHONDRIAL PROTEINS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR MIMICRY; OLIGOPEPTIDES; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; X-LINKED INHIBITOR OF APOPTOSIS PROTEIN;

EID: 3843086358     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0499108     Document Type: Article

References (19)

1. Kerr, J. F.; 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.
2. Thompson, C. B. Apoptosis in the pathogenesis and treatment of disease. Science 1995, 267, 1456-1462.
3. Nicholson, D. W. From bench to clinic with apoptosis-based therapeutic agents. Nature 2000, 407, 810-816.
4. Reed, J. C. Apoptosis-based therapies. Nat. Rev. Drug Discovery 2002, 1, 111-121.
5. Deveraux, Q. L.; Reed, J. C. IAP family proteins-suppressors of apoptosis. Genes Dev. 1999, 1, 239-252.
6. Salvesen, G. S.; Duckett, C. S. IAP proteins: blocking the road to death's door. Nat. Rev. Mol. Cell Biol. 2002, 3, 401-410.
7. Huang, Y.; Park, Y. C.; Rich, R. L.; Segal, D.; Myszka, D. G.; Wu, H. Structural basis of caspase inhibition by XIAP: differential roles of the linker versus the BIR domain. Cell 2001, 104, 781-790.
8. Ekert, P. G.; Silke, J.; Hawkins, C. J.; Verhagen, A. M.; Vaux, D. L. DIABLO promotes apoptosis by removing MIHA/XIAP from processed caspase 9. J. Cell Biol. 2001, 152, 483-490.
9. Srinivasula, S. M.; Hegde, R.; Saleh, A.; Datta, P.; Shiozaki, E.; Chai, J.; Lee, R. A.; Robbins, P. D.; Fernandes-Alnemri, T.; Shi, Y.; Alnemri, E. S. A conserved XIAP-interaction motif in caspase-9 and Smac/DIABLO regulates caspase activity and apoptosis. Nature 2001, 410, 112-116.
10. Shiozaki, E. N.; Chai, J.; Rigotti, D. J.; Riedl, S. J.; Li, P.; Srinivasula, S. M.; Alnemri, E. S.; Fairman, R.; Shi, Y. Mechanism of XIAP-mediated inhibition of caspase-9. Mol. Cell 2003, 11, 519-527.
11. Du, C.; Fang, M.; Li, Y.; Li, L.; Wang, X. Smac, a mitochondrial protein that promotes cytochrome c-dependent caspase activation by eliminating IAP inhibition. Cell 2000, 102, 33-42.
12. Verhagen, A. M.; Ekert, P. G.; Pakusch, M.; Silke, J.; Connolly, L. M.; Reid, G. E.; Moritz, R. L.; Simpson, R. J.; Vaux, D. L. Identification of DIABLO, a mammalian protein that promotes apoptosis by binding to and antagonizing IAP proteins. Cell 2000, 102, 43-53.
13. Wu, G.; Chai, J.; Suber, T. L.; Wu, J. W.; Du, C.; Wang, X.; Shi, Y. Structural basis of IAP recognition by Smac/DIABLO. Nature 2000, 408, 1008-1012.
14. Liu, Z.; Sun, C.; Olejniczak, E. T.; Meadows, R.; Betz, S. F.; Oost, T.; Herrmann, J.; Wu, J. C.; Fesik, S. W. Structural basis for binding of Smac/DIABLO to the XIAP BIR3 domain. Nature 2000, 408, 1004-1008.
15. Kipp, R. A.; Case, M. A.; Wist, A. D.; Cresson, C. M.; Carrell, M.; Griner, E.; Wiita, A.; Albiniak, P. A.; Chai, J.; Shi, Y.; Semmelhack, M. F.; McLendon, G. L. Molecular targeting of inhibitors of apoptosis proteins based on small molecule mimics of natural binding partners. Biochemistry 2002, 41, 7344-7349.
16. Fulda, S.; Wick, W.; Weller, M.; Debatin, K.-M. Smac agonists sensitize for Apo2L/TRAIL- or anticancer drug-induced apoptosis and induce regression of malignant glioma in vivo. Nat. Med. 2002, 8, 808-815.
17. Arnt, C. R.; Chiorean, M. V.; Heldebrant, M. P.; Gores, G. J.; Kaufmann, S. H. Synthetic Smac/DIABLO Peptides Enhance the Effects of Chemotherapeutic Agents by Binding XIAP and cIAP1 in Situ. J. Biol. Chem. 2002, 277, 44236-44243.
18. Yang, L.; Mashima, T.; Sato, S.; Mochizuki, M.; Sakamoto, H.; Yamori, T.; Oh-Hara, T.; Tsuruo, T. Predominant suppression of apoptosome by inhibitor of apoptosis protein in non-small cell lung cancer H460 cells: therapeutic effect of a novel polyarginine-conjugated Smac peptide. Cancer Res. 2003, 63, 831-837.
19. Lombart, H.-G.; Lubell, W. D. Rigid Dipeptide Mimetics: Efficient Synthesis of Enantiopure Indolizidinone Amino Acids. J. Org. Chem. 1996, 61, 9437.