Clasto-Lactacystin β-lactone

Cayman Chemical Item Number 70988

Omuralide; β-Clastolactacystin (CAS 154226-60-5)

Clasto-Lactacystin β-lactone (CAS 154226-60-5)

Description

Lactacystin is a microbial metabolite isolated from Streptomyces which is now widely used as a selective inhibitor of the 20S proteasome.^1,2,3 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.⁴ Clasto-lactacystin β-lactone irreversibly alkylates subunit X of the 20S proteasome.³ 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 signalling proteins within the treated cell.

1 Omura, S., Fujimoto, T.T., Otoguro, K., et al. Lactacystin, a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells. J Antibiot 44 113-116 (1991 Jan 1).

2 Corey, E.J., and Reichard, G.A. Total synthesis of lactacystin. J Am Chem Soc 114 10677-10678 (1992).

3 Fenteany, G., and Schreiber, S.L. Lactacystin, proteasome function, and cell fate. J Biol Chem 273(15) 8545-8548 (1998).

4 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).

Synonyms

Omuralide
β-Clastolactacystin

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

Molecular Formula

C₁₀H₁₅NO₄

Formula Weight

213.2

Formulation

A solution in methyl acetate

Purity

≥98%

Stability

2 years

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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O=C1C[C@@H]2OC(=O)[C@@]2(N1)C(O)C(C)C

Background Reading

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).

Corey, E.J., and Reichard, G.A. Total synthesis of lactacystin. J Am Chem Soc 114 10677-10678 (1992).

Fenteany, G., and Schreiber, S.L. Lactacystin, proteasome function, and cell fate. J Biol Chem 273(15) 8545-8548 (1998).

Omura, S., Fujimoto, T.T., Otoguro, K., et al. Lactacystin, a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells. J Antibiot 44 113-116 (1991 Jan 1).

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Size

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