Proteasome inhibition by a totally synthetic β-lactam related to salinosporamide A and omuralide

Journal of the American Chemical Society

Volumn 127, Issue 44, 2005, Pages 15386-15387

  Hogan, Philip C ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE; LACTACYSTIN BETA LACTONE; SALINOSPORAMIDE A; UNCLASSIFIED DRUG;

ARTICLE; DRUG HALF LIFE; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS;

BETA-LACTAMS; DRUG STABILITY; HALF-LIFE; KINETICS; LACTONES; PROTEASOME ENDOPEPTIDASE COMPLEX; PYRROLES;

EID: 27644594831     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056284a     Document Type: Article

References (22)

1. Feling, R. H.; Buchanan, G. O.; Mincer, T. J.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Angew. Chem., Int. Ed. 2003, 42, 355-357.
2. (a) Reviewed in: Corey, E. J.; Li, W.-D. Z. Chem. Pharm. Bull. 1999, 47, 1-10.
3. (b) Corey, E. J.; Reichard, G. A.; Kania, R. Tetrahedron Lett. 1993, 34, 6977-6980.
4. (c) Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677-10678.
5. (d) Fenteany, G.; Standaert, R. F.; Reichard, G. A.; Corey, E. J.; Schreiber, S. L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3358-3362.
6. (a) Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113-116.
7. (b) Omura, S.; Matsuzaki, K.; Fujimoto, T.; Kosuge, K.; Furuya, T.; Fujita, S.; Nakagawa, A. J. Antibiot. 1991, 44, 117-118.
8. i) proteasome inhibitor is currently in use and approved for the treatment of multiple myeloma. In addition, there are numerous ongoing clinical trials on the use of this agent for treatment of other malignant diseases. See: (a) Richardson, P. G.; Hideshima, T.; Anderson, K. C. Cancer Control 2003, 10, 361-369.
9. (b) Steinberg, D. The Scientist 2003, 17(S2), S18-S22.
10. (c) Adams, J., Proteasome Inhibitors in Cancer Therapy; Human Press: New York, 2004.
11. (a) Reddy, L. R.; Saravanan, P.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 6230-6231.
12. (b) Reddy, L. R.; Fournier, J.-F.; Reddy, B. V. S.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 8974-8976.
13. (c) Endo, A.; Danishefsky, S. J. J. Am. Chem. Soc. 2005, 127, 8298-8299.
14. (a) Xiang, C.; Wang, W.; Hruby, V. J. J. Org. Chem. 2002, 67, 3514-3517.
15. (b) Schmidt, U.; Respondek, M.; Lieberknect, A.; Werner, J.; Fischer, P. Synthesis 1989, 256-261.
16. Ghosez, L.; George-Koch, I.; Paling, L.; Houtekie, M.; Bovy, P.; Nshimyumuzika, P. Phan, T. Tetrahedron 1998, 54, 9207-9222.
17. See Supporting Information.
18. Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1987, 28, 4185-4188.
19. Isao, K.; Urabe, H. Tetrahedron Lett. 1981, 22, 5191-5194.
20. McCormack, T.; Baumeister, W.; Grenier, L.; Moomaw, C.; Plamondon, L.; Pramanik, B.; Slaughter, C.; Soucy, F.; Stein, R.; Zuhl, F.; Dick, L. J. Biol. Chem. 1996, 272, 26103-26109.
21. Obtained from Boston Biochem; Suc = succinyl; AMC = aminomethylcoumarin.
22. In vitro proteasome preparations are much less stable than the native in vivo proteins.