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E3652

Sigma-Aldrich

Epoxomicin

≥95% (HPLC), solid

Sinónimos:

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

Número de CAS:
134381-21-8
Número MDL:
MFCD03791061
Código UNSPSC:
12352202
ID de la sustancia en PubChem:
329799052
NACRES:
NA.77

Análisis

≥95% (HPLC)

formulario

solid

temp. de almacenamiento

−20°C

cadena 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

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

Clave InChI

DOGIDQKFVLKMLQ-JTHVHQAWSA-N

Descripción general

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.

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
L Meng et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(18), 10403-10408 (1999-09-01)
The proteasome regulates cellular processes as diverse as cell cycle progression and NF-kappaB activation. In this study, we show that the potent antitumor natural product epoxomicin specifically targets the proteasome. Utilizing biotinylated-epoxomicin as a molecular probe, we demonstrate that epoxomicin
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)
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)
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