Screening multicomponent reactions for X-linked inhibitor of apoptosis-baculoviral inhibitor of apoptosis protein repeats domain binder

Journal of Medicinal Chemistry

Volumn 54, Issue 3, 2011, Pages 890-900

  Monfardini, Ilaria ^a   Huang, Jui Wen ^b   Beck, Barbara ^a   Cellitti, Jason F ^b   Pellecchia, Maurizio ^b   Domling, Alexander ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

^b BURNHAM INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NEURONAL APOPTOSIS INHIBITORY PROTEIN; SECOND MITOCHONDRIAL ACTIVATOR OF CASPASE; X LINKED INHIBITOR OF APOPTOSIS;

ARTICLE; BIOMIMETICS; CONTROLLED STUDY; DRUG ACTIVITY; DRUG BINDING; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; PHARMACOPHORE; PROTEIN PROTEIN INTERACTION;

AMINO ACID MOTIFS; AMINO ACID SEQUENCE; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; DATABASES, FACTUAL; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; PEPTIDOMIMETICS; PIPERAZINES; PROTEIN BINDING; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAZOLES; THIAZOLES; THIAZOLIDINES; X-LINKED INHIBITOR OF APOPTOSIS PROTEIN;

EID: 79851498658     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101341m     Document Type: Article

References (55)

1. Yip, K. W.; Reed, J. C. Bcl-2 family proteins and cancer. Oncogene 2008, 27, 6398-6406.
2. Fulda, S. Inhibitor of apoptosis (IAPproteins: novel insights into the cancer-relevant targets for cell death induction. ACS Chem. Biol. 2009, 4, 499-501.
3. Sun, H.; Nikolovska-Coleska, Z.; Yang, C. Y.; Qian, D.; Lu, J.; Qiu, S.; Bai, L.; Peng, Y.; Cai, Q.; Wang, S. Design of small-molecule peptidic and nonpeptidicSmacmimetics. Acc. Chem. Res. 2008, 41, 1264-1277.
4. Schimmer, 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. (Pubitemid 38121594)
5. Huang, Y.; Rich, R. L.; Myszka, D. G.; Wu, H. Requirement of both the second and third BIR domains for the relief of X-linked inhibitor of apoptosis protein (XIAP)-mediated caspase inhibition by Smac. J. Biol. Chem. 2003, 278, 49517-19522.
6. Gao, Z.; Tian, Y.; Wang, J.; Yin, Q.; Wu, H.; Li, Y. M.; Jiang, X. A dimeric Smac/Diablo peptide directly relieves caspase-3 inhibition by XIAP: dynamic and cooperative regulation of XIAP by SMAC/DIABLO. J. Biol. Chem. 2007, 282, 30718-30727. (Pubitemid 350035215)
7. 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. (Pubitemid 40143163)
8. 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 ofnovel and potent Smac peptido-mimetics. Bioorg. Med. Chem. Lett. 2005, 15, 793-797. (Pubitemid 40143167)
9. Sun, H.; Nikolovska-Coleska, Z.; Lu, J.; Meagher, J. L.; Yang, C. Y.; Qiu, S.; Tomita, Y.; Ueda, Y.; Jiang, S.; Krajewski, K.; Roller, P. P.; Stuckey, J. A.; Wang, S. Design, synthesis, and characterization ofa potent, nonpeptide, cell-permeable, bivalent Smac mimetic that concurrently targets both the BIR2 and BIR3 domains in XIAP. J. Am. Chem. Soc. 2007, 129, 15279-15294. (Pubitemid 350247811)
10. Wist, A. D.; Gu, L.; Riedl, S. J.; Shi, Y.; McLendon, G. L. Structure-activity based study of the Smac-binding pocket within the BIR3 domain of XIAP. Bioorg. Med. Chem. 2007, 15, 2935-2943. (Pubitemid 46400464)
11. 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.; Olejniczak, E. T.; Oleksijew, A.; Oltersdorf, T.; Rosenberg, S. H.; Shoemaker, A. R.; Tomaselli, K. J.; Zou, H.; Fesik, S. W. Discovery of potent antagonists of the antiapoptotic protein XIAP for the treatment of cancer. J. Med. Chem. 2004, 47, 4417-4426. (Pubitemid 39096830)
12. Vucic, D.; Franklin, M. C.; Wallweber, H. J. A.; Das, K.; Eckelman, B. P.; Shin, H.; Elliott, L. O.; Kadkhodayan, S.; Deshayes, K.; Salvesen, G. S.; Fairbrother, W. J. Engineering ML-IAP to produce an extraordinarily potent caspase 9 inhibitor: implications for Smac-dependent anti-apoptotic activity of ML-IAP. Biochem. J. 2005, 385, 11-20.
13. Zobel, K.; Wang, L.; Varfolomeev, E.; Franklin, M. C.; Elliott, 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 IAPs. ACS Chem. Biol. 2006, 1, 525-533.
14. Gaither, A.; Porter, D.; Yao, Y.; Borawski, J.; Yang, G.; Donovan, J.; Sage, D.; Slisz, J.; Tran, M.; Straub, C.; Ramsey, T.; Iourgenko, V.; Huang, A.; Chen, Y.; Schlegel, R.; Labow, M.; Fawell, S.; Sellers, W. R.; Zawel, L. A Smac mimetic rescue screen reveals roles for inhibitor of apoptosis proteins in tumor necrosis factor-o signaling. Cancer Res. 2007, 67, 11493-11498.
15. Huang, J. W.; Zhang, Z.; Wu, B.; Cellitti, J. F.; Zhang, X.; Dahl, R.; Shiau, C. W.; Welsh, K.; Emdadi, A.; Stebbins, J. L.; Reed, J. C.; Pellecchia, M. Fragment-based design of small molecule X-linked inhibitor of apoptosis protein inhibitors. J. Med. Chem. 2008, 51, 7111-7118.
16. Chauhan, P. D.; Neri, P.; Velankar, M.; Podar, K.; Hideshima, T.; Fulciniti, M.; Tassone, P.; Raje, N.; Mitsiades, C.; Mitsiades, N.; Richardson, P.; Zawel, L.; Tran, M.; Munshi, N.; Anderson, K. C. Targeting mitochondrial factor Smac/DIABLO as therapy for multiple myeloma (MM). Blood 2007, 109, 1220-1227. (Pubitemid 46220671)
17. Sun, W.; Nikolovska-Coleska, Z.; Qin, D.; Sun, H.; Yang, C. Y.; Bai, L.; Qiu, S.; Wang, Y.; Ma, D.; Wang, S. Design, synthesis, and evaluation of a potent, cell-permeable, conformationally constrained second mitochondria derived activator of caspase (Smacmimetic. J. Med. Chem. 2009, 52, 593-596.
18. Czarna, A.; Beck, B.; Srivastava, S.; Popowicz, G. M.; Wolf, S.; Huang, Y.; Bista, M.; Holak, T. A.; Domling, A. Robust generation of lead compounds for protein-protein interactions by computational and MCR chemistry: p53/Hdm2 antagonists. Angew. Chem.. Int. Ed. 2010, 49, 5352-5356.
19. Popowicz, G. M.; Czarna, A.; Wolf, S.; Wang, K.; Wang, W.; Dömling, A.; Holak, T. A. Structures of low molecular weight inhibitors bound to MDMX and MDM2 reveal new approaches for p53-MDMX/MDM2 antagonist drug discovery. Cell Cycle 2010, 9, 1104-1111.
20. Bista, M.; Kowalska, K.; Janczyk, W.; Dömling, A.; Holak, T. Monitoring the effects of antagonists on protein-protein interactions with NMR spectroscopy. J. Am. Chem. Soc. 2009, 131, 7500-7501.
21. Dömling, A. Recent developments in isocyanide based multi-component reactions in applied chemistry. Chem. Rev. 2006, 106, 17-89. (Pubitemid 43159621)
22. Pirok, G.; Mate, N.; Varga, J.; Szegezdi, J.; Vargyas, M.; Dorant, S.; Csizmadia, F. Making "real" molecules in virtual space. J. Chem. Inf. Model. 2006, 46, 563-568.
23. Gerber, P. R.; Muller, K. MAB, a generally applicable molecular force field for structure modeling in medicinal chemistry. J. Com-out.-AidedMol. Des. 1995, 9, 251-268.
24. Dömling, A.; Ugi, I. The seven-component reaction. Angew. Chem.. Int. Ed. Engl. 1993, 32, 563-564.
25. Rossen, K.; Pye, P. J.; DiMichele, L. M.; Volante, R. P.; Reider, P. J. An efficient asymmetric hydrogenation approach to the synthesis of the Crixivan piperazine intermediate. Tetrahedron Lett. 1998, 39, 6823-6826. (Pubitemid 28407364)
26. Rossen, K.; Weissman, S. A.; Sager, J.; Reamer, R. A.; Askin, D.; Volante, R. P.; Reider, P. J. Asymmetric hydrogenation of tetra-hydropyrazines: synthesis of (S)-piperazine-2-tert-butylcarboxa-mide, an intermediate in the preparation of the HIV protease inhibitor indinavir. Tetrahedron Lett. 1995, 36, 6419-6422.
27. Heck, S.; Doomling, A. A versatile multi-component one-pot thia-zole synthesis. Synlett 2000, 424-426. (Pubitemid 30141091)
28. Nixey, T.; Hulme, C. Rapid generation of cis-constrained norsta-tine analogs using a TMSN3-modified Passerini MCC/N-capping strategy. Tetrahedron Lett. 2002, 43, 6833-6835. (Pubitemid 35245905)
29. Gröger, H.; Martens, J.; Goerlich, J. R.; Schmutzler, R. A novel synthetic approach to o-aminophosphine sulfide structures: the first addition of dimethylephosphine sulfide to 3-thiazolines. Phosphorus. Sulfur Silicon Relat. Elem. 1997, 128, 153-163. (Pubitemid 127387086)
30. Thiel, M.; Asinger, F.; Schmiedel, K. Uber die gemeinsame ein-wirkung von elementarem schwefel und gasförmigem ammoniak auf ketone VIII. Die kondensation von o-mercaptoaldehyden mit oxo-verbindungen und gasformigem ammoniak zu thiazolinen-A. Justus Liekigs Ann. Chem. 1958, 611, 121-131.
31. Martens, J.; Offermanns, H.; Scherberich, P. Facile synthesis of racemic cysteine. Angew. Chem.. Int. Ed. Engl. 1981, 20, 668.
32. Dömling, A.; Ugi, I. A new 5, 6-dihydro-2H-1, 3-oxazine synthesis via Asinger-type condensation. Tetrahedron 1993, 49, 9495-9500.
33. Hatam, M.; Tehranfar, D.; Martens, J. A novel and convenient route to phosphono oligopeptides derived from 1, 3-oxazolines, 1, 3-oxazines and 1, 3-thiazolines. Synth. Commun. 1995, 25, 1677-1688.
34. Gröger, H.; Hatam, M.; Martens, J. Synthese totalgeschützter, nichtproteinogener α-aminosäuren und oligopeptide aus 2H-1, 3-oxazinen und 2H-1, 3-benzoxazinen via Ugi-reaktion. Tetrahedron 1995, 51, 7173-7180.
35. Hatam, M.; Martens, J. Phosphinic acid analogues ofthiaproline and the related heterocyclic amino acids. Synth. Commun. 1995, 25, 2553-2559.
36. Hatam, M.; Goerlich, J. R.; Schmutzler, R.; Gröger, H.; Martens, J. The totally protected hydroxy containing α-amino phosphinic esters and α-amino phosphinoxides as well as their carbamoyl derivatives. Synth. Commun. 1996, 26, 3685-3698. (Pubitemid 26300375)
37. Dömling, A.; Illgen, K. 1-Isocyano-2-dimethylamino-alkenes: versatile reagents in diversity-oriented organic synthesis. Synthesis 2005, 662-667. (Pubitemid 40396062)
38. Henkel, B.; Sax, M.; Dömling, A. A new and efficient multi-component solid-phase synthesis of 2-acylaminomethylthiazoles. Tetrahedron Lett. 2003, 44, 3679-3682. (Pubitemid 36419594)
39. Kolb, J.; Beck, B.; Almstetter, M.; Heck, S.; Herdtweck, E.; Doomling, A. New MCRs: the first 4-component reaction leading to 2, 4-disubstituted thiazoles. Mol. Diversity 2003, 6, 297-313. (Pubitemid 38089868)
40. Kolb, J.; Beck, B.; Doomling, A. Simultaneous assembly of the β-lactam and the thiazole moiety by a new multicomponent reaction. Tetrahedron Lett. 2002, 43, 6897-6901. (Pubitemid 35246075)
41. Dömling, A.; Beck, B.; Eichelberger, U.; Sakamuri, S.; Menon, S.; Chen, Q. Z.; Lu, Y.; Wessjohann, L. A. Total synthesis of tubulysin U and V. Angew. Chem.. Int. Ed. 2007, 46, 2347-2348.
42. Lau, H. H.; Schöllkopf, U. Synthesen mit α-metallierten isocyani-den, LII. Synthesen mit α-metallierten isocyaniden, LII. Synthese von 2-alkyl-und 2-acyl-1-methylimidazol-4-carbon-sauremethylestern aus (Z)-β-dimethylamino-α-isocyanacrylsouremethylester und alkyl-oder acylhalogeniden. Liebigs Ann. Chem. 1982, 2093-2095.
43. Sandham, D. A.; Barker, L.; Beattie, D.; Beer, D.; Bidlake, L.; Bentley, D.; Butler, K. D.; Craig, S.; Farr, D.; Ffoulkes-Jones, C.; Fozard, J. R.; Haberthuer, S.; Howes, C.; Hynx, D.; Jeffers, S.; Keller, T. H.; Kirkham, P. A.; Maas, J. C.; Mazzoni, L.; Nicholls, A. Synthesis and biological properties of novel glucocorticoid androstene C-17 furoate esters. Bioorg. Med. Chem. 2004, 12, 5213-5224. (Pubitemid 39206285)
44. Sabot, C.; Kumar, K. A.; Meunier, S.; Mioskowski, C. Aconvenient aminolysis of esters catalyzed by 1, 5, 7-triazabicyclo[4.4.0]dec-5-ene (TBDunder solvent-free conditions. Tetrahedron Lett. 2007, 48, 3863-3866. (Pubitemid 46669655)
45. Nunami, K.; Yamada, M.; Fukui, T.; Matsumoto, K. A novel synthesis of methyl 1, 5-disubstituted imidazole-4-carboxylates using 3-bromo-2- isocyanoacrylates (BICA). J. Org. Chem. 1994, 59, 7635-7642.
46. Fehrentz, J. A.; Castro, B. An efficient synthesis of optically active α-(t-butoxycarbonylamino)-aldehydes from α-amino acids. Synthesis 1983, 676-678.
47. Bockbrader, K. M.; Tan, M.; Sun, Y. A small molecule Smac-mimic compound induces apoptosis and sensitizes TRAIL-and etoposide-induced apoptosis in breast cancer cells. Oncogene 2005, 24, 7381-7388. (Pubitemid 41622242)
48. 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.; Olejniczak, E. T.; Oleksijew, A.; Oltersdorf, T.; Rosenberg, S. H.; Shoemaker, A. R.; Tomaselli, K. J.; Zou, H.; Fesik, S. W. Discovery of potent antagonists of the antiapoptotic protein XIAP for the treatment of cancer. J. Med. Chem. 2004, 47, 4417-4426. (Pubitemid 39096830)
49. Spencer, R. W. High-throughput screening of historic collections observations on file size, biological targets, and file diversity. Biotechnol. Bioeng. 1998, 61, 61-67. (Pubitemid 28561945)
50. Jacoby, E.; Boettcher, A.; Mayr, L. M.; Brown, N.; Jenkins, J. L.; Kallen, J.; Engeloch, C.; Schopfer, U.; Furet, P.; Masuya, K.; Lisztwan, J. Chemogenomics; Jacoby, E., Ed.; Methods in Molecular Biology, Vol. 575; Springer: Heidelberg, Germany, 2009; pp 173-194.
51. Kussie, P. H.; Gorina, S.; Marechal, V.; Elenbaas, B.; Moreau, B.; 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)
52. Shuker, S. B.; Hajduk, P. J.; Meadows, R. P.; Fesik, S. W. Discovering high-affinity ligands for proteins: SAR by NMR. Science 1996, 274, 1531-1534. (Pubitemid 26403929)
53. Goddard, T. D.; Kneller, D. G. SPARKY, version 3; San Francisco, CA.
54. Rega, M. F.; Reed, J. C.; Pellecchia, M. Robust lanthanide-based assays for the detection of anti-apoptotic Bcl-2-family protein antagonists. Bioorg. Chem. 2007, 35, 113-120. (Pubitemid 46365827)
55. Kangas, L.; Gronroos, M.; Nieminen, A. L. Bioluminescence of cellular ATP: a new method for evaluating cytotoxic agents in vitro. Med. Biol. 1984, 62, 338-343. (Pubitemid 15117242)