E3652

Epoxomicin

Name: Epoxomicin
Brand: SIGMA

≥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

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About This Item

CAS Number:

134381-21-8

NACRES:

NA.77

PubChem Substance ID:

329799052

UNSPSC Code:

12352202

MDL number:

MFCD03791061

Product Name

Epoxomicin, ≥95% (HPLC), solid

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

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 key

DOGIDQKFVLKMLQ-JTHVHQAWSA-N

assay

≥95% (HPLC)

form

solid

storage temp.

−20°C

Quality Level

100

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 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.

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

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Differential degradation of full-length and cleaved ataxin-7 fragments in a novel stable inducible SCA7 model

Yu X, et al.

Journal of Molecular Neuroscience, 47(2), 219-233 (2012)

Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo antiinflammatory activity

Meng L, et al.

Proceedings of the National Academy of Sciences of the USA, 96(18), 10403-10408 (1999)

From epoxomicin to carfilzomib: chemistry, biology, and medical outcomes.

Kyung Bo Kim et al.

Natural product reports, 30(5), 600-604 (2013-04-12)

The initial enthusiasm following the discovery of a pharmacologically active natural product is often fleeting due to the poor prospects for its ultimate clinical application. Despite this, the ever-changing landscape of modern biology has a constant need for molecular probes

The selective proteasome inhibitors lactacystin and epoxomicin can be used to either up-or down-regulate antigen presentation at nontoxic doses

Schwarz K, et al.

Journal of Immunology, 164(12), 6147-6157 (2000)

Chymase uptake by cardiomyocytes results in myosin degradation in cardiac volume overload

Powell PC, et al.

Heliyon, 5(4), e01397-e01397 (2019)

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