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Epoxomicin (CAS 134381-21-8)

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Application:A potent chymotrypsin-like proteasome inhibitor (CTRL)
CAS Number:134381-21-8
Purity:95%
Molecular Weight:554.7
Molecular Formula:C28H50N4O7
Refer to Certificate of Analysis for lot specific data (including water content).
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Epoxomicin sc-201298 100 µg $205
Description
Epoxomicin is a potent proteasome inhibitor, primarily inhibiting the activity of CTRL(chymotrypsin-like proteasome). The novel α-epoxy ketone moiety of Epoxomicin forms covalent bonds with residues in particular catalytic subunits of the enzyme, disabling activity. The trypsin-like and peptidyl-glutamyl peptide hydrolyzing behavior of the proteasome were both inhibited by Epoxomicin as well (at 100 and 1,000-fold slower rates, respectively). Bone formation is heavily regulated by the ubiquitin-proteasome pathway, and Epoxomicin was shown to increase both bone volume and bone formation rates in rodents. Another study demonstrates that exposure to Epoxomicin and other proteasome inhibitors leads to dopaminergic cell death, producing a model of Parkinson's disease in vivo. Epoxomicin is an inhibitor of 20S Proteasome.
Technical Information
Physical State:Solid
Solubility:Soluble in DMSO (10 mg/mL), and dichloromethane:methanol (9:1). Insoluble in water.
Storage:Store at -20° C
Boiling Point:739.24 °C at 760 mmHg
Density:1.12 g/cm3
Refractive Index:n20D 1.5
IC50:proteasome activity: IC50 = 4 nM; B16-F10, HCT116, and Moser solid tumor cells, as well as P388 and K562 leukemia cells: IC50 = 2-44 nM
Safety and Reference Information
WGK Germany:3
PubChem CID:3035402
Merck Index:14: 3630
MDL Number:MFCD03791061
SMILES:CC[C@H](C)[C@@H](C(=O)NC(=O)[C@H]([C@@H](C)O)NC(CC(C)C)C(=O)[C@]1(CO1)C)NC(= O)[C@H]([C@@H](C)CC)N(C)C(=O)C
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
References
1. Hanada, M., et al. 1992. J. Antibiot. 45: 1746-1752. PMID: 1468981
2. Meng, L., et al. 1999. Proc. Natl. Acad. Sci. U.S.A. 96: 10403-10408. PMID: 10468620
3. Schwarz, K., et al. 2000. J. Immunol. 164: 6147-6157. PMID: 10843664
4. Princiotta, M.F., et al. 2001. Proc. Natl. Acad. Sci. U.S.A. 98: 513-518. PMID: 11149939
5. Garrett, I.R., et al. 2003. J. Clin. Invest. 111: 1771-1782. PMID: 12782679
6. McNaught, K.S., et al. 2004. Ann. Neurol. 56: 149-162. PMID: 15236415
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