Epoxomicin

SKU: orb1300427

Description

Epoxomicin is a potent and selective proteasome inhibitor that primarily targets the chymotrypsin-like (CH-L) activity of the 20S proteasome. It is widely used in research to study proteasome function, protein degradation pathways, and has demonstrated anti-inflammatory and anti-cancer effects in both cellular and animal models.

Research Area

Protein Biochemistry, Stem Cell & Developmental Biology

Key Properties

• CAS Number: 134381-21-8
• MW: 554.73
• Purity: >98%
• Formula: C₂₈H₅₀N₄O₇
• SMILES: CC[C@H](C)[C@H](NC(=O)[C@H]([C@@H](C)CC)N(C)C(C)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(=O)[C@@]1(C)CO1
• Target: Proteasome
• Solubility: Soluble in DMSO (up to 10 mg/ml).

Bioactivity

• In Vivo:
  Epoxomicin (0.58 mg/kg per day) reduces the CS response by 44% relative to the control group of mice treated with vehicle alone. Epoxomicin (2.9 mg/kg) potently inhibits the irritant-associated inflammatory response by 95% when ear edema measurements are made 24 hours postchallenge in mice.
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• In Vitro:
  Epoxomicin covalently binds to the LMP7, X, MECL1, and Z catalytic subunits of the proteasome. Epoxomicin (100 nM) results in a 30-fold increase in the levels of p53 protein, a known target of the proteasome, in HUVECs. Epoxomicin (10 μM) results in the accumulation of ubiquitinated proteins in HeLa cells. Epoxomicin (10 μM) inhibits IκBα degradation by 10-fold in HeLa cells. Epoxomicin (10 μM) produces a significant dose-dependent reduction in TNF-α-stimulated NF-κB DNA-binding activity in HeLa cells. Epoxomicin inhibits proliferating of EL4 lymphoma cells with biotinylated chimerae with IC50 of 4 nM. Epoxomicin (1 μM) leads to a reduction of LCMV GP33 presentation and an enhancement of GP276 presentation. Epoxomicin inhibits growth of Babesia bigemina with IC50 of 4 nM. Epoxomicin (0.5 mg/kg and 0.05 mg/kg) results in peak parasitemia levels of 34.8% and 42.3% in B. microti. Epoxomicin (100 nM) decreases the total parasitemia by 78%, 86% and 77% in Plasmodium falciparum. Epoxomicin (10 μM) inhibits gametogenesis and exflagellation as well as development into oocysts of anopheles mosquitoes.
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Storage & Handling

• Storage: -20°C
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

covalently, cytotoxicities, BBB, BU-4061T, Apoptosis, 20S proteasome, Epoxomicin, Epoxyketone-containing, Proteasome

Chemical structure of Epoxomicin.

Compound Identifiers

PubChem CID

11226684