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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

Epoxomicin

Cayman Chemical Item Number 10007806

BU 4061T (CAS 134381-21-8)

Epoxomicin (CAS 134381-21-8)

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Description

Epoxomicin is a potent anti-tumor agent isolated from Actinomycetes that is used as a selective and irreversible inhibitor of the 20S proteasome. It inhibits proteasome activity in cell growth assays with an IC50 value of 4 nM and demonstrates potent cytotoxicity against B16-F10, HCT116, and Moser solid tumor cells, as well as P388 and K562 leukemia cells with IC50 values ranging from 2-44 nM.1,2 By inhibiting osteoblast proteasome activity, epoxomicin stimulates bone formation at concentrations as low as 10 nM.3 Intraperitoneal injection of 1.5 mg/kg epoxomicin given daily for two weeks induces Parkinson’s-like symptoms in rats and addition of 100 nM epoxomicin to rat ventral midbrain cultures results in apoptosis specific to dopaminergic neurons.4,5 Epoxomicin-induced parkinsonism can be a useful model to examine mechanisms and therapies for the disease.

1 Kim, K.B., Myung, J., Sin, N., et al. Proteasome inhibition by the natural products epoxomicin and dihydroeponemycin: Insights into specificity and potency. Bioorg Med Chem Lett 9 3335-3340 (1999).

2 Hanada, M., Sugawara, K., Kaneta, K., et al. Epoxomicin, a new antitumor agent of microbial origin. J Antibiot 45(11) 1746-1752 (1992).

3 Garrett, I.R., Chen, D., Gutierrez, G., et al. Selective inhibitors of the osteoblast proteasome stimulate bone formation in vivo and in vitro. J Clin Invest 111(11) 1771-1782 (2003).

4 McNaught, K.S.M., Perl, D.P., Brownell, A., et al. Systemic exposure to proteasome inhibitors causes a progressive model of Parkinson’s disease. Ann Neurol 56 149-162 (2004).

5 Rideout, H.J., Lang-Rollin, I.C.J., Savalle, M., et al. Dopaminergic neurons in rat ventral midbrain cultures undergo selective apoptosis and form inclusions, but do not up-regulate iHSP70, following proteasomal inhibition. J Neurochem 93 1304-1313 (2005).

Synonyms
  • BU 4061T
Formal Name N-​acetyl-​N-​methyl-​L-​isoleucyl-​L-​isoleucyl-​N-​[(1S)-​3-​methyl-​1-​[[(2R)-​2-​methyloxiranyl]carbonyl]butyl]-​L-​threoninamide
CAS Number 134381-21-8
Molecular Formula C28H50N4O7
Formula Weight 554.7
Formulation A solution in DMSO
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CC[C@H]​(C)​[C@@H]​(NC(=O)​[C@H]​([C@@H]​(C)​CC)​N(C)​C(=O)​C)​C(=O)​N[C@@H]​([C@@H]​(C)​O)​C(=O)​N[C@H]​(CC(C)​C)​C(=O)​[C@]​1(C)​OC1

Background Reading

Hanada, M., Sugawara, K., Kaneta, K., et al. Epoxomicin, a new antitumor agent of microbial origin. J Antibiot 45(11) 1746-1752 (1992).

Kim, K.B., Myung, J., Sin, N., et al. Proteasome inhibition by the natural products epoxomicin and dihydroeponemycin: Insights into specificity and potency. Bioorg Med Chem Lett 9 3335-3340 (1999).

Rideout, H.J., Lang-Rollin, I.C.J., Savalle, M., et al. Dopaminergic neurons in rat ventral midbrain cultures undergo selective apoptosis and form inclusions, but do not up-regulate iHSP70, following proteasomal inhibition. J Neurochem 93 1304-1313 (2005).

McNaught, K.S.M., Perl, D.P., Brownell, A., et al. Systemic exposure to proteasome inhibitors causes a progressive model of Parkinson’s disease. Ann Neurol 56 149-162 (2004).

Garrett, I.R., Chen, D., Gutierrez, G., et al. Selective inhibitors of the osteoblast proteasome stimulate bone formation in vivo and in vitro. J Clin Invest 111(11) 1771-1782 (2003).

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Size Price Quantity Subtotal
25 µg $50.00 $0.00
50 µg $95.00 $0.00
100 µg $180.00 $0.00
250 µg $400.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-02-12. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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