Omuralide and vibralactone: Differences in the proteasome-β-lactone- γ-lactam binding scaffold alter target preferences

Angewandte Chemie - International Edition

Volumn 53, Issue 2, 2014, Pages 571-574

  List, Anja ^a   Zeiler, Evelyn ^b   Gallastegui, Nerea ^a   Rusch, Marion ^c   Hedberg, Christian ^c   Sieber, Stephan A ^a   Groll, Michael ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b HARVARD UNIVERSITY   (United States)

^c MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

Author keywords

click chemistry; drug development; natural products; proteasome; protein crystallography

Indexed keywords

CLICK CHEMISTRY; DRUG DEVELOPMENT; NATURAL PRODUCTS; PROTEASOMES; PROTEIN CRYSTALLOGRAPHY;

PROTEINS;

ESTERS;

APT2 PROTEIN, HUMAN; LACTACYSTIN BETA LACTONE; LACTAM; LACTONE; LYPLA1 PROTEIN, HUMAN; PROTEASOME; PROTEASOME INHIBITOR; THIOL ESTER HYDROLASE; VIBRALACTONE;

ARTICLE; BINDING SITE; CELL SURVIVAL; CHEMISTRY; CLICK CHEMISTRY; DOSE RESPONSE; DRUG ANTAGONISM; DRUG DEVELOPMENT; DRUG EFFECT; HELA CELL LINE; HUMAN; NATURAL PRODUCTS; PROTEIN BINDING; PROTEIN CRYSTALLOGRAPHY; PROTEIN SUBUNIT; STRUCTURE ACTIVITY RELATION;

CLICK CHEMISTRY; DRUG DEVELOPMENT; NATURAL PRODUCTS; PROTEASOME; PROTEIN CRYSTALLOGRAPHY;

BINDING SITES; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; HELA CELLS; HUMANS; LACTAMS; LACTONES; PROTEASOME INHIBITORS; PROTEIN BINDING; PROTEIN SUBUNITS; STRUCTURE-ACTIVITY RELATIONSHIP; THIOLESTER HYDROLASES;

EID: 84891763651     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201308567     Document Type: Article

References (46)

1. A. Hershko, A. Ciechanover, Annu. Rev. Biochem. 1998, 67, 425-479.
2. M. Groll, L. Ditzel, J. Lowe, D. Stock, M. Bochtler, H. D. Bartunik, R. Huber, Nature 1997, 386, 463-471
3. M. Unno, T. Mizushima, Y. Morimoto, Y. Tomisugi, K. Tanaka, N. Yasuoka, T. Tsukihara, Structure 2002, 10, 609-618
4. E. Huber, M. Basler, R. Schwab, W. Heinemeyer, C. J. Kirk, M. Groettrup, M. Groll, Cell 2012, 148, 727-738.
5. J. Löwe, D. Stock, B. Jap, P. Zwickl, W. Baumeister, R. Huber, Science 1995, 268, 533-539.
6. P. G. Richardson, P. Sonneveld, M. W. Schuster, E. A. Stadtmauer, T. Facon, J. L. Harousseau, D. Ben-Yehuda, S. Lonial, H. Goldschmidt, D. Reece, J. Blade, M. Boccadoro, J. D. Cavenagh, A. L. Boral, D. L. Esseltine, P. Y. Wen, A. A. Amato, K. C. Anderson, J. S. Miguel, Br. J. Haematol. 2009, 144, 895-903.
7. G. Cavaletti, A. J. Jakubowiak, Leuk. Lymphoma 2010, 51, 1178-1187.
8. E. M. Huber, M. Groll, Angew. Chem. 2012, 124, 8838-8850
9. Angew. Chem. Int. Ed. 2012, 51, 8708-8720
10. A. Rentsch, D. Landsberg, T. Brodmann, L. Bulow, A. K. Girbig, M. Kalesse, Angew. Chem. 2013, 125, 5560-5599
11. Angew. Chem. Int. Ed. 2013, 52, 5450-5488.
12. K. Fostier, A. DeBecker, R. Schots, OncoTargets Ther. 2012, 5, 237-244.
13. M. L. Stein, P. Beck, M. Kaiser, R. Dudler, C. F. Becker, M. Groll, Proc. Natl. Acad. Sci. USA 2012, 109, 18367-18371.
14. G. Fenteany, R. F. Standaert, W. S. Lane, S. Choi, E. J. Corey, S. L. Schreiber, Science 1995, 268, 726-731.
15. S. Omura, K. Matsuzaki, T. Fujimoto, K. Kosuge, T. Furuya, S. Fujita, A. Nakagawa, J. Antibiot. 1991, 44, 117-118.
16. G. Fenteany, R. F. Standaert, G. A. Reichard, E. J. Corey, S. L. Schreiber, Proc. Natl. Acad. Sci. USA 1994, 91, 3358-3362
17. E. J. Corey, W. Li, T. Nagamitsu, Angew. Chem. 1998, 110, 1784-1787
18. Angew. Chem. Int. Ed. 1998, 37, 1676-1679
19. E. J. Corey, W.-D. Z. Li, T. Nagamitsu, G. Fenteany, Tetrahedron 1999, 55, 3305-3316.
20. R. H. Feling, G. O. Buchanan, T. J. Mincer, C. A. Kauffman, P. R. Jensen, W. Fenical, Angew. Chem. 2003, 115, 369-371
21. Angew. Chem. Int. Ed. 2003, 42, 355-357.
22. M. Groll, R. Huber, B. C. Potts, J. Am. Chem. Soc. 2006, 128, 5136-5141.
23. M. Groll, B. C. Potts, Curr. Top. Med. Chem. 2011, 11, 2850-2878
24. T. A. Gulder, B. S. Moore, Angew. Chem. 2010, 122, 9534-9556
25. Angew. Chem. Int. Ed. 2010, 49, 9346-9367.
26. I. M. Shah, K. R. Lees, C. P. Pien, P. J. Elliott, Br. J. Clin. Pharmacol. 2002, 54, 269-276.
27. V. R. Macherla, S. S. Mitchell, R. R. Manam, K. A. Reed, T. H. Chao, B. Nicholson, G. Deyanat-Yazdi, B. Mai, P. R. Jensen, W. F. Fenical, S. T. Neuteboom, K. S. Lam, M. A. Palladino, B. C. Potts, J. Med. Chem. 2005, 48, 3684-3687.
28. D. Z. Liu, F. Wang, T. G. Liao, J. G. Tang, W. Steglich, H. J. Zhu, J. K. Liu, Org. Lett. 2006, 8, 5749-5752.
29. M. J. Evans, B. F. Cravatt, Chem. Rev. 2006, 106, 3279-3301
30. M. Fonovic, M. Bogyo, Expert Rev. Proteomics 2008, 5, 721-730
31. T. Böttcher, M. Pitscheider, S. A. Sieber, Angew. Chem. 2010, 122, 2740-2759
32. Angew. Chem. Int. Ed. 2010, 49, 2680-2698.
33. E. Zeiler, N. Braun, T. Bottcher, A. Kastenmuller, S. Weinkauf, S. A. Sieber, Angew. Chem. 2011, 123, 11193-11197
34. Angew. Chem. Int. Ed. 2011, 50, 11001-11004.
35. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
36. Angew. Chem. Int. Ed. 2002, 41, 2596-2599
37. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064
38. D. S. Johnson, E. Weerapana, B. F. Cravatt, Future Med. Chem. 2010, 2, 949-964.
39. K. B. Kim, J. Myung, N. Sin, C. M. Crews, Bioorg. Med. Chem. Lett. 1999, 9, 3335-3340.
40. L. R. Dick, A. A. Cruikshank, A. T. Destree, L. Grenier, T. A. McCormack, F. D. Melandri, S. L. Nunes, V. J. Palombella, L. A. Parent, L. Plamondon, R. L. Stein, J. Biol. Chem. 1997, 272, 182-188.
41. M. A. Gräwert, M. Groll, Chem. Commun. 2012, 48, 1364-1378.
42. A. F. Kisselev, A. L. Goldberg, Chem. Biol. 2001, 8, 739-758.
43. P. Beck, C. Dubiella, M. Groll, Biol. Chem. 2012, 393, 1101-1120.
44. M. Rusch, T. J. Zimmermann, M. Burger, F. J. Dekker, K. Gormer, G. Triola, A. Brockmeyer, P. Janning, T. Bottcher, S. A. Sieber, I. R. Vetter, C. Hedberg, H. Waldmann, Angew. Chem. 2011, 123, 10012-10016
45. Angew. Chem. Int. Ed. 2011, 50, 9838-9842.
46. F. J. Dekker, O. Rocks, N. Vartak, S. Menninger, C. Hedberg, R. Balamurugan, S. Wetzel, S. Renner, M. Gerauer, B. Scholermann, M. Rusch, J. W. Kramer, D. Rauh, G. W. Coates, L. Brunsveld, P. I. Bastiaens, H. Waldmann, Nat. Chem. Biol. 2010, 6, 449-456.