clasto-Lactacystin β-lactone

CHF 350.00
In stock
AG-CN2-0442-C100100 µgCHF 350.00
More Information
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
  • 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
  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)
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