Epoxomicin

Proteasome inhibitor

Catalog No. SIH-388

0 out of 5 based on 0 customer ratings
CAS No. 134381-21-8
Molecular Formula C28H50N4O7
SKU: SIH-388 Categories: ,

Clear
SIH-388_Epoxomicin_Chemical_Structure.png
Product Name Epoxomicin
Description

Proteasome inhibitor

Purity >95%
CAS No. 134381-21-8
Molecular Formula C28H50N4O7
Molecular Weight 554.7
Field of Use Not for use in humans. Not for use in diagnostics or therapeutics. For in vitro research use only.

Properties

Storage Temperature -20ºC
Shipping Temperature Shipped Ambient
Product Type Inhibitor
Solubility Soluble in DMSO (15 mg/ml) or dichloromethane:methanol (9:1); insoluble in water.
Source Synthetic
Appearance White solid
SMILES [C@@H](CC)(C)[C@@H](C(N[C@H](C(N[C@@H]([C@@H](C)O)C(=O)N[C@H](C(=O)NCC(=O)[C@]1(C)OC1)CC(C)C)=O)[C@H](CC)C)=O)N(C)C
InChI 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
InChIKey DOGIDQKFVLKMLQ-JTHVHQAWSA-N
Safety Phrases Classification: Caution. Substance not yet fully tested.
Safety Phrases:
S22 - Do not breathe dust
S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection
S24/25 - Avoid contact with skin and eyes
Cite This Product Epoxomicin (StressMarq Biosciences Inc., Victoria BC CANADA, Catalog # SIH-388)

Biological Description

Alternative Names N-Acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]-L-threoninamide
Research Areas Cell Signaling
PubChem ID 11226684
Scientific Background Epoxomicin is a potent, cell-permeable, and selective inhibitor of the proteasome, originally isolated from an Actinomycetes strain for its antitumor properties. In neuroscience, Epoxomicin is widely used to study the ubiquitin-proteasome system (UPS), a critical pathway for protein degradation and cellular homeostasis in neurons. Dysfunction of the UPS is a hallmark of several neurodegenerative diseases, including Alzheimer’s, Parkinson’s, and Huntington’s disease, where misfolded or aggregated proteins accumulate. Epoxomicin inhibits the chymotrypsin-like, trypsin-like, and PGPH activities of the proteasome, making it a valuable tool for dissecting proteostasis mechanisms. It also indirectly activates autophagy, a compensatory degradation pathway, by blocking UPS function. Additionally, Epoxomicin suppresses NF-κB activation and inflammation, further supporting its use in neuroinflammatory models. Its dual role in modulating protein clearance and inflammatory signaling makes it highly relevant in neurodegenerative disease research.
References 1. F. Yang, et al. (2009) Neurosci. Lett. 454: 203.
2. K. Ohkawa, et al. (2004) Int. J. Oncol. 24: 425.
3. K. Schwarz, et al. (2000) J. Immunol. 164: 6147.
4. L. Meng, et al. (1999) PNAS. 96: 10403.
5. K.B. Kim, et al. (1999) Bioorg. Med. Chem. Lett. 9: 3335.
6. N. Sin, et al. (1999) Bioorg. Med. Chem. Lett. 9: 2283.
7. M. Hanada, et al. (1992) J. Antibiot. (Tokyo) 45: 1746.

Product Images

<p>Chemical structure of Epoxomicin (SIH-388), a Proteasome inhibitor. CAS #: 134381-21-8. Molecular Formula: C28H50N4O7. Molecular Weight: 554.7 g/mol.</p>

Chemical structure of Epoxomicin (SIH-388), a Proteasome inhibitor. CAS #: 134381-21-8. Molecular Formula: C28H50N4O7. Molecular Weight: 554.7 g/mol.

Reviews

Reviews

There are no reviews yet.

Be the first to review “Epoxomicin”

Your email address will not be published. Required fields are marked *