Lactacystin (CAS 133343-34-7) || Cayman Chemical

Lactacystin

Cayman Chemical Item Number 70980

(CAS 133343-34-7)

Lactacystin (CAS 133343-34-7)

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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Size

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50 µg 
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500 µg 
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1 mg 
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