E3652

Epoxomicin

≥95% (HPLC), solid

• Synonym(s): 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
• NACRES: NA.77
• PubChem Substance ID: 329799052
• UNSPSC Code: 12352202
• MDL number: MFCD03791061
• Assay: ≥95% (HPLC)
• Form: solid

Properties

• Quality Segment: 100
• assay: ≥95% (HPLC)
• form: solid
• storage temp.: −20°C
• SMILES string: 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
• 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

Description

General description

Epoxomicin is a linear peptide consisting of a threonine or serine residue with α′, β′-epoxyketone derived from leucine or a γ,δ-dehydroleucine. It is a natural product isolated from Actinomyces sp., and is a cell-permeable, potent, selective and irreversible proteasome inhibitor.

Application

Epoxomicin has been used:

• as an ubiquitin–proteosome system (UPS) inhibitor in pheochromocytoma PC12 cells
• as a proteasome inhibitor in mammary epithelial MCF-10A cells
• as a proteasome inhibitor in chymotryptic assay in cardiomyocytes

Biochem/physiol Actions

Epoxomicin, a natural product isolated from Actinomyces sp., is a cell-permeable, potent, selective and irreversible proteasome inhibitor.

Epoxomicin binds covalently to the catalytic subunits of proteasome. It forms an adduct with target proteins. It inhibits chymotrypsin-like activity of the proteasome. Epoxomicin also inhibits the nuclear factor κ light chain enhancer of activated B cells (NF-κB) mediated proinflammatory signalling pathway. It is also a potent antitumor and anti-inflammatory agent.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)