A highly selective proteasome inhibitor
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Epoxomicin

Item No. 10007806

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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
Synonyms
  • BU 4061T
Molecular Formula
C28H50N4O7
Formula Weight
554.7
Purity
≥95%
Formulation
A 250 µg/ml solution in DMSO
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/ml
SMILES
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
InChi Code
InChI=1S/C28H50N4O7/c1-11-16(5)21(30-27(38)23(17(6)12-2)32(10)19(8)34)25(36)31-22(18(7)33)26(37)29-20(13-15(3)4)24(35)28(9)14-39-28/h15-18,20-23,33H,11-14H2,1-10H3,(H,29,37)(H,30,38)(H,31,36)/t16-,17-,18+,20-,21-,22-,23-,28+/m0/s1
InChi Key
DOGIDQKFVLKMLQ-JTHVHQAWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 µg

    $70

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    50 µg

    $129

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    100 µg

    $242

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    250 µg

    $535

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    Cayman Chemical
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    Product 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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(23), 3335-3340 (1999).

    2. Hanada, M., Sugawara, K., Kaneta, K., et al. Epoxomicin, a new antitumor agent of microbial origin. J. Antibiot. (Tokyo) 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.L., et al. Systemic exposure to proteasome inhibitors causes a progressive model of Parkinson’s disease. Ann. Neurol. 56(1), 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(5), 1304-1313 (2005).

    Product Citations

    Njomen, E., Osmulski, P.A., Jones, C.L., et al. Small molecule modulation of proteasome assembly. Biochemistry 57(28), 4214-4224 (2018).