clasto-Lactacystin beta-lactone
Product Code: AG-CN2-0442
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0442-C100 | 100 ug | £260.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Blue Ice
Storage:
-20°C
Further Information
Alternate Names/Synonyms:
Omuralide
Appearance:
White to off-white solid.
CAS:
154226-60-5
EClass:
32160000
Form (Short):
solid
Handling Advice:
Protect from light.
InChi:
InChI=1S/C10H15NO4/c1-4(2)6(12)10-7(15-9(10)14)5(3)8(13)11-10/h4-7,12H,1-3H3,(H,11,13)/t5-,6+,7+,10?/m1/s1
InChiKey:
FWPWHHUJACGNMZ-OEUIFBLYSA-N
Long Description:
Chemical. CAS: 154226-60-5. Formula: C10H15NO4. MW: 213.2. 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.
MDL:
MFCD01076526
Molecular Formula:
C10H15NO4
Molecular Weight:
213.2
Other data:
In vitro lactacystin does not react with the proteasome. It rather undergoes a spontaneous conversion (lactonization) to the active metabolite clasto-lactacystin beta-lactone.
Package Type:
Vial
Product 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.
Purity:
>95% (HPLC)
SMILES:
CC(C)[C@H](O)C12NC(=O)[C@H](C)[C@@H]1OC2=O
Solubility Chemicals:
Soluble in DMSO or acetonitrile. Undergoes hydrolysis in aqueous buffers.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 1 year after receipt when stored at -20°C. Store solutions at -20°C in the dark.
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)