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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

Lactacystin

Cayman Chemical Item Number 70980

(CAS 133343-34-7)

Lactacystin (CAS 133343-34-7)

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Description

Lactacystin is a microbial metabolite isolated from Streptomyces that is now widely used as a selective inhibitor of the 20 S proteasome.1,2,3 Lactacystin was first characterized by its ability to induce differentiation and inhibit cell cycle progression in several tumor cell lines. At concentrations from 2 to 10 µM, lactacystin induces the outgrowth of neurites in the neuroblastoma cell line Neuro 2A.4 Lactacystin irreversibly alkylates subunit X of the 20 S proteasome.3 The concomitant inhibition of proteasome peptidase activity results in the accumulation of a variety of ubiquitinated proteins which would normally undergo rapid degradation. Thus, the effects of lactacystin are pleiotropic and depend substantially on the expression pattern of signalling proteins within the treated cell.

1 Omura, S., Fujimoto, T.T., Otoguro, K., et al. Lactacystin, a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells. J Antibiot 44 113-116 (1991 Jan 1).

2 Corey, E.J., and Reichard, G.A. Total synthesis of lactacystin. J Am Chem Soc 114 10677-10678 (1992).

3 Fenteany, G., and Schreiber, S.L. Lactacystin, proteasome function, and cell fate. J Biol Chem 273(15) 8545-8548 (1998).

4 Fenteany, G., Standaert, R.F., Reichard, G.A., et al. A β-lactone related to lactacystin induces neurite outgrowth in a neuroblastoma cell line and inhibits cell cycle progression in an osteosarcoma cell line. Proc Natl Acad Sci USA 91 3358-3362 (1994).

Formal Name 3S-​hydroxy-​2R-​(1-​hydroxy-​2-​methylpropyl)-​4R-​methyl-​5-​oxo-​2-​pyrrolidinecarboxylate-​N-​acetyl-​L-​cysteine
CAS Number 133343-34-7
Molecular Formula C15H24N2O7S
Formula Weight 376.4
Formulation A clear film
Purity >98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=C(SC[C@@H]​(C(O)​=O)​N(C(C)​=O)​[H]​)​[C@@]​1(N([H]​)​C([C@H]​(C)​[C@@H]​1O)​=O)​[C@H]​(C(C)​C)​O

Background Reading

Fenteany, G., Standaert, R.F., Reichard, G.A., et al. A β-lactone related to lactacystin induces neurite outgrowth in a neuroblastoma cell line and inhibits cell cycle progression in an osteosarcoma cell line. Proc Natl Acad Sci USA 91 3358-3362 (1994).

Corey, E.J., and Reichard, G.A. Total synthesis of lactacystin. J Am Chem Soc 114 10677-10678 (1992).

Fenteany, G., and Schreiber, S.L. Lactacystin, proteasome function, and cell fate. J Biol Chem 273(15) 8545-8548 (1998).

Omura, S., Fujimoto, T.T., Otoguro, K., et al. Lactacystin, a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells. J Antibiot 44 113-116 (1991 Jan 1).

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Lactacystin is available in the following screening library:

Size Price Quantity Subtotal
50 µg $38.00 $0.00
100 µg $72.00 $0.00
500 µg $304.00 $0.00
1 mg $532.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-12. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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