426102
clasto-Lactacystin β-Lactone
A highly specific, cell-permeable, and irreversible 20S proteasome inhibitor.
Synonym(s):
clasto-Lactacystin β-Lactone, Omuralide, Proteasome Inhibitor IX
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About This Item
Empirical Formula (Hill Notation):
C10H15NO4
CAS Number:
Molecular Weight:
213.23
UNSPSC Code:
12352202
NACRES:
NA.77
MDL number:
Form:
solid
Storage condition:
OK to freeze
Quality Segment
form
solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
color
white
solubility
DMSO: 3 mg/mL
shipped in
ambient
storage temp.
−20°C
SMILES string
N1[C@@]2([C@@H](OC2=O)[C@H](C1=O)C)[C@@H](O)C(C)C
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
InChI key
FWPWHHUJACGNMZ-NBBQQVJHSA-N
General description
A cell-permeable, irreversible inhibitor of the trypsin-like, chymotrypsin-like, and peptidylglutamyl peptide hydrolysis activities of the 20S proteasome. It is believed that in vitro, the natural product, Lactacystin (Cat. No. 426100), acts as a precursor for clasto-lactacystin β-lactone, and the later is the sole species that interacts with the proteasome. Inhibits the proteasome in intact cells (IC50 approximately 1 µM). clasto-Lactacystin β-lactone shows 5-10 fold greater potency than lactacystin in vitro.
A highly specific, cell-permeable, and irreversible 20S proteasome inhibitor. It is believed that in vitro, the natural product Lactacystin (Cat. No. 426100) acts as a precursor for clasto-lactacystin β-lactone and that the latter is the sole species that interacts with the proteasome.
Biochem/physiol Actions
Cell permeable: yes
Primary Target
20S proteasome
20S proteasome
Product does not compete with ATP.
Reversible: no
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C. Rapidly hydrolyzed in aqueous buffers.
Other Notes
Corey, E.J., and Wei-Dong, Z. 1999. Chem. Pharm. Bull. 47, 1.
Dick, L.R., et al. 1997. J. Biol. Chem. 272, 182.
Dick, L.R., et al. 1996. J. Biol. Chem.271, 7273.
Fenteany, G., et al. 1995. Science268, 726.
Dick, L.R., et al. 1997. J. Biol. Chem. 272, 182.
Dick, L.R., et al. 1996. J. Biol. Chem.271, 7273.
Fenteany, G., et al. 1995. Science268, 726.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
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Storage Class
11 - Combustible Solids
wgk
WGK 2
Certificates of Analysis (COA)
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