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226811 Clasto-Lactacystin beta-lactone (Omuralide) CAS: 154226-60-5

Specifications
References
CAS Number
154226-60-5
Grade
Highly Purified
Molecular Formula
C10H15NO4
Molecular Weight
213.2
EU Commodity Code
38220090
Shipping Temp
Blue Ice
Storage Temp
-20°C

In vitro lactacystin does not react with the proteasome. It rather undergoes a spontaneous conversion (lactonization) to the active metabolite clasto-lactacystin beta-lactone. Potent and selective irreversible and cell permeable proteasome inhibitor. Inhibits the chymotrypsin-like, trypsin-like and caspase-like peptidase activity of the proteasome. The active metabolite of lactacystin with higher potency since it does not require hydrolysis in order to become cell permeable. Calpain and cathepsin inhibitor. Apoptosis inducer. Anticancer compound. Induces differentiation and inhibits cell cycle progression in several tumor cell lines. Induces neuritogenesis. Autophagy inducer.

Molecular Formula
C10H15NO4
Molecular Weight
213.2
Solubility
Soluble in DMSO or acetonitrile. Undergoes hydrolysis in aqueous buffers.
Storage and Stability
Stable for at least 1 year after receipt when stored at -20°C. Store solutions at -20°C in the dark.
Purity
≥95% (HPLC)
Form
Supplied as a white to off-white solid.
Important Note
This product as supplied is intended for research use only, not for use in human, therapeutic or diagnostic applications without the expressed written authorization of United States Biological.
References
1. Inhibition of proteasome activities and subunit-specific amino-terminal threonine modification by lactacystin: G. Fenteany, et al.; Science 268, 726 (1995). 2. Lactacystin and clasto-lactacystin beta-lactone modify multiple proteasome beta-subunits and inhibit intracellular protein degradation and major histocompatibility complex class I antigen presentation: A. Craiu, et al.; J. Biol. Chem. 272, 56 (1997). 3. Mechanistic studies on the inactivation of the proteasome by lactacystin in cultured cells: L.R. Dick, et al.; J. Biol. Chem. 272, 182 (1997). 4. Lactacystin, proteasome function, and cell fate: G. Fenteany & S.L. Schreiber; J. Biol. Chem. 273, 8545 (1998) (Review). 5. Prediction of the mechanism of action of omuralide (clasto-lactacystin beta-lactone) on human cathepsin A based on a structural model of the yeast proteasome beta5/PRE2-subunit/omuralide complex: S. Aikawa, et al.; Biochim. Biophys. Acta 1764, 1372 (2006). 6. Importance of the different proteolytic sites of the proteasome and the efficacy of inhibitors varies with the protein substrate: A.F. Kisselev, et al.; J. Biol. Chem. 281, 8582 (2006). 7. Effect of proteasome inhibitor clasto-lactacystin-beta-lactone on the proteome of the haloarchaeon Haloferax volcanii: P.A. Kirkland, et al.; Microbiology 153, 2271 (2007).
USBio References
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