clasto-Lactacystin beta-Lactone CAS: 154226-60-5
MF: C10H15NO4
MW: 213.23
An active species of lactacystin proteasome inhibition.

clasto-Lactacystin β-Lactone (CAS 154226-60-5)

clasto-Lactacystin β-Lactone | CAS 154226-60-5 is rated 5.0 out of 5 by 1.
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Synonym: Omuralide
Application: An active species of lactacystin proteasome inhibition
CAS Number: 154226-60-5
Purity: ≥95%
Molecular Weight: 213.23
Molecular Formula: C10H15NO4
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Clasto-Lactacystin β-Lactone is the β-lactone active form of the Streptomyces antibiotic lactacystin, a widely employed inhibitor of the 20S proteasome. Hydrolysis of lactacystin releases N-acetyl-L-cysteine and reveals the inactive clasto-Lactacystin dihydroxy carboxylic acid, which then cyclizes to form the active β-lactone species. Clasto-Lactacystin β-Lactone is thought to be the primary compound that interacts with the proteasome, as conditions stabilizing to lactacystin that prevent accumulation of the β-lactone also display diminished inhibition of the proteasome. Clasto-Lactacystin β-Lactone is an inhibitor of cathepsin A.


References

1. Dick, L.R., et al. 1996. J. Biol. Chem. 271: 7273-7276. PMID: 8631740
2. Craiu, A., et al. 1997. J. Biol. Chem. 272: 13437-13445. PMID: 9148969
3. Corey, E.J. and Li, W.D. 1999. Chem. Pharm. Bull. 47: 1-10. PMID: 9987821
4. Barringhaus, K.G., et al. 2007. Exp Clin Cardiol. 12: 119-124. PMID: 18650992

Formulation :
A solution in methyl acetate
Physical State :
Liquid
Solubility :
Soluble in DMSO (25 mg/ml), DMF, ethanol, ethyl acetate (Hot), methanol, pyridine, and acetonitrile.
Storage :
Store at -20° C
Boiling Point :
57° C
Refractive Index :
n20D 1.52 (Predicted)
IC50 :
Inhibition of NF-kB activation in HEK293 cells: IC50 = 1600 nM (human); Cytotoxic activity against RPMI 8226 cells: IC50 = 3300 nM (human); 20S proteasome: IC50 = 49 nM; trypsin-like (T-L) activity of rabbit 20S proteasome: IC50 = 540 nM (rabbit); chymotrypsin-like (CT-L) activity of rabbit 20S proteasome: IC50 = 57 nM (rabbit)
pK Values :
pKa: 13.33 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
2
PubChem CID :
9794358
MDL Number :
MFCD01076526
SMILES :
CC1C2C(C(=O)O2)(NC1=O)C(C(C)C)O

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clasto-Lactacystin beta-Lactone  Product Citations

See how others have used clasto-Lactacystin beta-Lactone. Click on the entry to view the PubMed entry .

Citations 1 to 3 of 3 total

PMID: # 28261569  Rucks, EA. et al. 2017. Frontiers in cellular and infection microbiology. 7: 40.

PMID: # 20599975  Wills, J. et al. 2010. Exp Neurol. 225: 210-218.

PMID: # 15684420  Jiang, HY. et al. 2005. J. Biol. Chem. 280: 14189-14202.

Citations 1 to 3 of 3 total
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Rated 5 out of 5 by from Wills et al Wills et al. (PubMed ID 20599975) used clasto-Lactacystin -Lactone to inhibit degradation of targeted proteins by the 26S proteasome. -SCBT Publication Review
Date published: 2015-04-10
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