AdipoGen Life Sciences

clasto-Lactacystin β-lactone

CHF 350.00

In stock

AG-CN2-0442-C100100 µgCHF 350.00

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Product Details
Synonyms	Omuralide
Product Type	Chemical
Properties
Formula	C₁₀H₁₅NO₄
MW	213.2
CAS	154226-60-5
Purity Chemicals	≥95% (HPLC)
Appearance	White to off-white solid.
Solubility	Soluble in DMSO or acetonitrile. Undergoes hydrolysis in aqueous buffers.
Other Product Data	In vitro lactacystin does not react with the proteasome. It rather undergoes a spontaneous conversion (lactonization) to the active metabolite clasto-lactacystin β-lactone.
InChi Key	FWPWHHUJACGNMZ-OEUIFBLYSA-N
Smiles	CC(C)[C@H](O)C12NC(=O)[C@H](C)[C@@H]1OC2=O
Shipping and Handling
Shipping	BLUE ICE
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light.
Use/Stability	Stable for at least 1 year after receipt when stored at -20°C. Store solutions at -20°C in the dark.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Description

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 (Prod. No. AG-CN2-0104) 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.

Product References

Inhibition of proteasome activities and subunit-specific amino-terminal threonine modification by lactacystin: G. Fenteany, et al.; Science 268, 726 (1995)
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)
Mechanistic studies on the inactivation of the proteasome by lactacystin in cultured cells: L.R. Dick, et al.; J. Biol. Chem. 272, 182 (1997)
Lactacystin, proteasome function, and cell fate: G. Fenteany & S.L. Schreiber; J. Biol. Chem. 273, 8545 (1998) (Review)
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)
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)
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)

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