A selective inhibitor of the 20S proteasome
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Parent Compound(s)
70980Lactacystin
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Clasto-Lactacystin β-lactone

Item No. 70988

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1R-[1S-1hydroxy-2-methylpropyl]-4R-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
CAS Number
154226-60-5
Synonyms
  • β-Clastolactacystin
  • Omuralide
Molecular Formula
C10H15NO4
Formula Weight
213.2
Purity
≥95%
Formulation (Request formulation change)
A 500 µg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
SMILES
O=C1C[C@@H]2OC(=O)[C@@]2(N1)C(O)C(C)C
InChi Code
InChI=1S/C9H13NO4/c1-4(2)7(12)9-5(14-8(9)13)3-6(11)10-9/h4-5,7,12H,3H2,1-2H3,(H,10,11)/t5-,7-,9-/m0/s1
InChi Key
HKJIEDVBDJEURI-GCHGDONOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    50 µg

    $77

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    100 µg

    $139

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    500 µg

    $578

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    Product Description

    Clasto-lactacystin β-lactone was later identified as the active metabolite of lactacystin, resulting from the elimination of cysteine and the formation of a reactive β-lactone. Both lactacystin and its β-lactone metabolite induce differentiation and inhibit cell cycle progression in several tumor cell lines.1 Clasto-lactacystin β-lactone irreversibly alkylates subunit X of the 20S proteasome.2 It is at least 10 times more active than the parent compound; this increased activity may be a function of increased cell permeability. Inhibition of proteasome peptidase activity results in the accumulation of a variety of ubiquitinated proteins which would normally undergo rapid degradation. Thus, the effects of clasto-lactacystin β-lactone are pleiotropic and depend substantially on the expression pattern of signaling proteins within the treated cell.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fenteany, G., Standaert, R.F., Reichard, G.A., et al. A β-lactone related to lactacystin induces neurite outgrowth in a neuroblastoma cell line and inhibits cell cycle progression in an osteosarcoma cell line. Proc. Natl. Acad. Sci. USA 91, 3358-3362 (1994).

    2. Fenteany, G., and Schreiber, S.L. Lactacystin, proteasome function, and cell fate. The Journal of Biological Chemisty 273(15), 8545-8548 (1998).