Discovery of inhibitors of the wnt and hedgehog signaling pathways through the catalytic enantioselective synthesis of an iridoid-inspired compound collection

Angewandte Chemie - International Edition

Volumn 52, Issue 47, 2013, Pages 12404-12408

  Takayama, Hiroshi ^a   Jia, Zhi Jun ^a,b   Kremer, Lea ^a   Bauer, Jonathan O ^b   Strohmann, Carsten ^b   Ziegler, Slava ^a   Antonchick, Andrey P ^a,b   Waldmann, Herbert ^a,b  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b TU DORTMUND UNIVERSITY   (Germany)

Author keywords

asymmetric catalysis; cycloaddition; inhibitors; iridoids; signaling pathways

Indexed keywords

ASYMMETRIC CATALYSIS; AZOMETHINE YLIDES; COMPOUND COLLECTIONS; ENANTIOSELECTIVE SYNTHESIS; HEDGEHOG SIGNALING PATHWAYS; IRIDOIDS; POTENT INHIBITOR; SIGNALING PATHWAYS;

CHELATION; CORROSION INHIBITORS; CYCLOADDITION;

SIGNALING;

IRIDOID; SONIC HEDGEHOG PROTEIN; WNT PROTEIN;

ANIMAL; ARTICLE; ASYMMETRIC CATALYSIS; CATALYSIS; CELL LINE; CELL SURVIVAL; CHEMISTRY; CYCLOADDITION; DRUG ANTAGONISM; DRUG EFFECT; DRUG SCREENING; HEK293 CELL LINE; HUMAN; INHIBITORS; METABOLISM; MOUSE; SIGNAL TRANSDUCTION; SIGNALING PATHWAYS; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ASYMMETRIC CATALYSIS; CYCLOADDITION; INHIBITORS; IRIDOIDS; SIGNALING PATHWAYS;

ANIMALS; CATALYSIS; CELL LINE; CELL SURVIVAL; CYCLOADDITION REACTION; DRUG EVALUATION, PRECLINICAL; HEDGEHOG PROTEINS; HEK293 CELLS; HUMANS; IRIDOIDS; MICE; SIGNAL TRANSDUCTION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; WNT PROTEINS;

EID: 84887521002     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201306948     Document Type: Article

References (94)

1. K. Kumar, H. Waldmann, Angew. Chem. 2009, 121, 3272-3290
2. Angew. Chem. Int. Ed. 2009, 48, 3224-3242
3. M. Kaiser, S. Wetzel, K. Kumar, H. Waldmann, Cell. Mol. Life Sci. 2008, 65, 1186-1201
4. R. S. Bon, H. Waldmann, Acc. Chem. Res. 2010, 43, 1103-1114
5. S. Wetzel, R. S. Bon, K. Kumar, H. Waldmann, Angew. Chem. 2011, 123, 10990-11018
6. Angew. Chem. Int. Ed. 2011, 50, 10800-10826.
7. F. E. Koehn, G. T. Carter, Nat. Rev. Drug Discovery 2005, 4, 206-220
8. K. S. Lam, Trends Microbiol. 2007, 15, 279-289
9. D. J. Newman, G. M. Cragg, J. Nat. Prod. 2007, 70, 461-477
10. A. Ganesan, Curr. Opin. Chem. Biol. 2008, 12, 306-317
11. A. L. Harvey, Drug Discovery Today 2008, 13, 894-901
12. J. W. H. Li, J. C. Vederas, Science 2009, 325, 161-165
13. T. F. Molinski, D. S. Dalisay, S. L. Lievens, J. P. Saludes, Nat. Rev. Drug Discovery 2009, 8, 69-85; for previous studies by our research group, see
14. S. Basu, B. Ellinger, S. Rizzo, C. Deraeve, M. Schürmann, H. Preut, H.-D. Arndt, H. Waldmann, Proc. Natl. Acad. Sci. USA 2011, 108, 6805-6810
15. H. Dückert, V. Pries, V. Khedkar, S. Menninger, H. Bruss, A. W. Bird, Z. Maliga, A. Brockmeyer, P. Janning, A. Hyman, S. Grimme, M. Schürmann, H. Preut, K. Hubel, S. Ziegler, K. Kumar, H. Waldmann, Nat. Chem. Biol. 2012, 8, 179-184
16. T. Voigt, C. Gerding-Reimers, T. N. T. Tuyen, S. Bergmann, H. Lachance, B. Schölermann, A. Brockmeyer, P. Janning, S. Ziegler, H. Waldmann, Angew. Chem. 2013, 125, 428-432
17. Angew. Chem. Int. Ed. 2013, 52, 410-414
18. V. Eschenbrenner-Lux, H. Dückert, V. Khedkar, H. Bruss, H. Waldmann, K. Kumar, Chem. Eur. J. 2013, 19, 2294-2304
19. T. Knoth, K. Warburg, C. Katzka, A. Rai, A. Wolf, A. Brockmeyer, P. Janning, T. F. Reubold, S. Eschenburg, D. J. Manstein, K. Hübel, M. Kaiser, H. Waldmann, Angew. Chem. 2009, 121, 7376-7381
20. Angew. Chem. Int. Ed. 2009, 48, 7240-7245.
21. H. Clevers, R. Nusse, Cell 2012, 149, 1192-1205
22. B. T. MacDonald, K. Tamai, X. He, Dev. Cell 2009, 17, 9-26
23. A. Klaus, W. Birchmeier, Nat. Rev. Cancer 2008, 8, 387-398
24. N. Barker, H. Clevers, Nat. Rev. Drug Discovery 2006, 5, 997-1014
25. C. Y. Logan, R. Nusse, Annu. Rev. Cell Dev. Biol. 2004, 20, 781-810
26. A. Kochegarov, Expert Opin. Ther. Pat. 2009, 19, 275-281
27. F. Osakada, Z. B. Jin, Y. Hirami, H. Ikeda, T. Danjyo, K. Watanabe, Y. Sasai, M. Takahashi, J. Cell Sci. 2009, 122, 3169-3179
28. T. Reya, H. Clevers, Nature 2005, 434, 843-850
29. D. L. Zhang, L. J. Gu, L. Liu, C. Y. Wang, B. S. Sun, Z. Li, C. K. Sung, Biochem. Biophys. Res. Commun. 2009, 378, 149-151
30. C. Fathke, L. Wilson, K. Shah, B. Kim, A. Hocking, R. Moon, F. Isik, BMC Cell Biol. 2006, 7, 4
31. D. Silkstone, H. Hong, B. A. Alman, Nat. Clin. Pract. Rheumatol. 2008, 4, 413-419.
32. L. L. Rubin, F. J. de Sauvage, Nat. Rev. Drug Discovery 2006, 5, 1026-1033
33. J. M. Y. Ng, T. Curran, Nat. Rev. Cancer 2011, 11, 493-501
34. S. Peukert, K. Miller-Moslin, ChemMedChem 2010, 5, 500-512
35. M. R. Tremblay, K. McGovern, M. A. Read, A. C. Castro, Curr. Opin. Chem. Biol. 2010, 14, 428-435
36. B. Z. Stanton, L. F. Peng, Mol. BioSyst. 2010, 6, 44-54
37. N. Mahindroo, C. Punchihewa, N. Fujii, J. Med. Chem. 2009, 52, 3829-3845
38. P. Heretsch, L. Tzagkaroulaki, A. Giannis, Bioorg. Med. Chem. 2010, 18, 6613-6624.
39. M. Lepourcelet, Y. N. P. Chen, D. S. France, H. Wang, P. Crews, F. Petersen, C. Bruseo, A. W. Wood, R. A. Shivdasani, Cancer Cell 2004, 5, 91-102
40. N. Chung, S. Marine, E. A. Smith, R. Liehr, S. T. Smith, L. Locco, E. Hudak, A. Kreamer, A. Rush, B. Roberts, M. B. Major, R. T. Moon, W. Arthur, M. Cleary, B. Strulovici, M. Ferrer, Assay Drug Dev. Technol. 2010, 8, 286-294
41. K. H. Emami, C. Nguyen, H. Ma, D. H. Kim, K. W. Jeong, M. Eguchi, R. T. Moon, J. L. Teo, H. Y. Kim, S. H. Moon, J. R. Ha, M. Kahn, Proc. Natl. Acad. Sci. USA 2004, 101, 12682-12687
42. B. Chen, M. E. Dodge, W. Tang, J. Lu, Z. Ma, C. W. Fan, S. Wei, W. Hao, J. Kilgore, N. S. Williams, M. G. Roth, J. F. Amatruda, C. Chen, L. Lum, Nat. Chem. Biol. 2009, 5, 100-107.
43. S. Sinha, J. K. Chen, Nat. Chem. Biol. 2006, 2, 29-30
44. J. K. Chen, J. Taipale, M. K. Cooper, P. A. Beachy, Genes Dev. 2002, 16, 2743-2748
45. J. K. Chen, J. Taipale, K. E. Young, T. Maiti, P. A. Beachy, Proc. Natl. Acad. Sci. USA 2002, 99, 14071-14076
46. M. F. Strand, S. R. Wilson, J. L. Dembinski, D. D. Holsworth, A. Khvat, I. Okun, D. Petersen, S. Krauss, PLOS one 2011, 6, e 19904
47. A. Büttner, K. Seifert, T. Cottin, V. Sarli, L. Tzagkaroulaki, S. Scholz, A. Giannis, Bioorg. Med. Chem. 2009, 17, 4943-4954
48. K. Seifert, A. Büttner, S. Rigol, N. Eilert, E. Wandel, A. Giannis, Bioorg. Med. Chem. 2012, 20, 6465-6481.
49. H. Waldmann, V. Khedkar, H. Dückert, M. Schürmann, I. M. Oppel, K. Kumar, Angew. Chem. 2008, 120, 6975-6978
50. Angew. Chem. Int. Ed. 2008, 47, 6869-6872
51. A. P. Antonchick, C. Gerding-Reimers, M. Catarinella, M. Schürmann, H. Preut, S. Ziegler, D. Rauh, H. Waldmann, Nat. Chem. 2010, 2, 735-740
52. A. P. Antonchick, S. Lõpez-Tosco, J. Parga, S. Sievers, M. Schürmann, H. Preut, S. Höing, H. R. Schöler, J. Sterneckert, D. Rauh, H. Waldmann, Chem. Biol. 2013, 20, 500-509
53. P.-Y. Dakas, J. A. Parga, S. Höing, H. R. Schöler, J. Sterneckert, K. Kumar, H. Waldmann, Angew. Chem. 2013, 125, 9755-9760
54. Angew. Chem. Int. Ed. 2013, 52, 9576-9581.
55. B. Dinda, D. R. Chowdhury, B. C. Mohanta, Chem. Pharm. Bull. 2009, 57, 765-796
56. B. Dinda, S. Debnath, R. Banik, Chem. Pharm. Bull. 2011, 59, 803-833
57. B. Dinda, S. Debnath, Y. Harigaya, Chem. Pharm. Bull. 2007, 55, 689-728
58. B. Dinda, S. Debnath, Y. Harigaya, Chem. Pharm. Bull. 2007, 55, 159-222.
59. E. L. Ghisalberti, Phytomedicine 1998, 5, 147-163
60. R. Tundis, M. R. Loizzo, F. Menichini, G. A. Statti, F. Menichini, Mini-Rev. Med. Chem. 2008, 8, 399-420
61. A. Viljoen, N. Mncwangi, I. Vermaak, Curr. Med. Chem. 2012, 19, 2104-2127.
62. J. Adrio, J. C. Carretero, Chem. Commun. 2011, 47, 6784-6794
63. C. Nájera, J. M. Sansano, M. Yus, J. Braz. Chem. Soc. 2010, 21, 377-412
64. L. M. Stanley, M. P. Sibi, Chem. Rev. 2008, 108, 2887-2902
65. H. Pellissier, Tetrahedron 2007, 63, 3235-3285
66. V. Nair, T. D. Suja, Tetrahedron 2007, 63, 12247-12275
67. G. Pandey, P. Banerjee, S. R. Gadre, Chem. Rev. 2006, 106, 4484-4517.
68. B. M. Trost, S. M. Silverman, J. Am. Chem. Soc. 2012, 134, 4941-4954
69. S. Reboredo, E. Reyes, J. L. Vicario, D. Badía, L. Carrillo, A. De Cõzar, F. P. Cossío, Chem. Eur. J. 2012, 18, 7179-7188
70. E. Conde, D. Bello, A. de Cõzar, M. Sánchez, M. A. Vázquez, F. P. Cossío, Chem. Sci. 2012, 3, 1486-1491
71. M. González-Esguevillas, J. Adrio, J. C. Carretero, Chem. Commun. 2012, 48, 2149-2151
72. Z.-L. He, H.-L. Teng, C.-J. Wang, Angew. Chem. 2013, 125, 3006-3010
73. Angew. Chem. Int. Ed. 2013, 52, 2934-2938
74. M. González-Esguevillas, J. Adrio, J. C. Carretero, Chem. Commun. 2013, 49, 4649-4651
75. J. Hernández-Toribio, S. Padilla, J. Adrio, J. C. Carretero, Angew. Chem. 2012, 124, 8984-8988
76. Angew. Chem. Int. Ed. 2012, 51, 8854-8858
77. X. Jing, C. He, D. P. Dong, L. L. Yang, C. Y. Duan, Angew. Chem. 2012, 124, 10274-10278
78. Angew. Chem. Int. Ed. 2012, 51, 10127-10131.
79. M. Potowski, J. O. Bauer, C. Strohmann, A. P. Antonchick, H. Waldmann, Angew. Chem. 2012, 124, 9650-9654
80. Angew. Chem. Int. Ed. 2012, 51, 9512-9516
81. M. Potowski, M. Schürmann, H. Preut, A. P. Antonchick, H. Waldmann, Nat. Chem. Biol. 2012, 8, 428-430
82. A. P. Antonchick, H. Schuster, H. Bruss, M. Schürmann, H. Preut, D. Rauh, H. Waldmann, Tetrahedron 2011, 67, 10195-10202
83. H. Waldmann, E. Blaser, M. Jansen, H. P. Letschert, Angew. Chem. 1994, 106, 717-719
84. Angew. Chem. Int. Ed. Engl. 1994, 33, 683-685.
85. K. Willert, K. A. Jones, Genes Dev. 2006, 20, 1394-1404.
86. S. Park, J. Gwak, M. Cho, T. Song, J. Won, D. E. Kim, J. G. Shin, S. Oh, Mol. Pharmacol. 2006, 70, 960-966.
87. M. A. Koch, L. O. Wittenberg, S. Basu, D. A. Jeyaraj, E. Gourzoulidou, K. Reinecke, A. Odermatt, H. Waldmann, Proc. Natl. Acad. Sci. USA 2004, 101, 16721-21676
88. M. A. Koch, A. Schuffenhauer, M. Scheck, S. Wetzel, M. Casaulta, A. Odermatt, P. Ertl, H. Waldmann, Proc. Natl. Acad. Sci. USA 2005, 102, 17272-17277
89. A. Nören-Müller, I. Reis-Corrêa, Jr., H. Prinz, C. Rosenbaum, K. Saxena, H. J. Schwalbe, D. Vestweber, G. Cagna, S. Schunk, O. Schwarz, H. Schiewe, H. Waldmann, Proc. Natl. Acad. Sci. USA 2006, 103, 10606-10611.
90. J. Skolnick, M. Gao, Proc. Natl. Acad. Sci. USA 2013, 110, 9344-9349.
91. X. Wu, S. Ding, Q. Ding, N. S. Gray, P. G. Schultz, J. Am. Chem. Soc. 2002, 124, 14520-14521
92. M. M. Beloti, L. S. Bellesini, A. L. Rosa, Cell Biol. Int. 2005, 29, 537-541
93. X. Wu, J. Walker, J. Zhang, S. Ding, P. G. Schultz, Chem. Biol. 2004, 11, 1229-1238
94. X.-J. Li, B.-Y. Hu, S. A. Jones, Y.-S. Zhang, Y. Sha, T. Lavaute, Z.-W. Du, Stem Cells 2008, 26, 886-893.