EPOXOMICIN

Product Name: EPOXOMICIN
CAS No.: 134381-21-8
Chemical Name: EPOXOMICIN
Synonyms: CS-1626;BU-4061T;EPOXOMICIN;Aids010837;Aids-010837;Epoxomicin, 99.5%;BU-4061T,Aids010837;Epoxomicin(BU-4061T);EPOXOMICIN, SYNTHETIC;EPOXOMICIN;BU4061T;BU-4061T
CBNumber: CB3198331
Molecular Formula: C28H50N4O7
Formula Weight: 554.72
MOL File: 134381-21-8.mol

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EPOXOMICIN Property

Melting point:: 107-109°
alpha: D24.5 -66.1 ± 0.4° (c = 0.5 in MeOH)
Boiling point:: 795.7±60.0 °C(Predicted)
Density: 1.117±0.06 g/cm3(Predicted)
storage temp.: -20°C
solubility: Soluble in DMSO (up to 10 mg/ml).
pka: 13.02±0.46(Predicted)
form: solid
color: White
Stability:: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 2 months.
InChIKey: DOGIDQKFVLKMLQ-JTHVHQAWSA-N

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Safety

WGK Germany: 3
HS Code: 29299090

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: E3652
Product name: Epoxomicin
Purity: ≥95% (HPLC), solid
Packaging: 50μg
Price: $327
Updated: 2024/03/01

Sigma-Aldrich

Product number: 324801
Product name: Epoxomicin
Purity: InSolution, ≥95%
Packaging: 50μg
Price: $201
Updated: 2024/03/01

Sigma-Aldrich

Product number: 324800
Product name: Epoxomicin, Synthetic
Purity: Epoxomicin, Synthetic, CAS 134381-21-8, is a potent, specific, and irreversible inhibitor of chymotrypsin-like, trypsin-like, and peptidyl-glutamyl peptide hydrolyzing activities of the proteasome.
Packaging: 100μG
Price: $360
Updated: 2024/03/01

Cayman Chemical

Product number: 10007806
Product name: Epoxomicin
Purity: ≥98%
Packaging: 25μg
Price: $63
Updated: 2024/03/01

Cayman Chemical

Product number: 10007806
Product name: Epoxomicin
Purity: ≥98%
Packaging: 50μg
Price: $117
Updated: 2024/03/01

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EPOXOMICIN Chemical Properties,Usage,Production

Description

Epoxomicin (134381-21-8) is a potent, selective and cell permeable irreversible inhibitor of the 20S proteasome.1 It does not inhibit non-proteasomal proteases such as papain, chymotrypsin, trypsin, calpain and cathepsin B at concentrations up to 50 μM.1 Epoxomicin was isolated from Actinomycete strain Q996-17 and displayed in vivo antitumor activity against B16 melanoma cells.2 Epoxomicin caused a progressive model of Parkinson’s disease in various systems.3,4,5 This model has been disputed.6,7

Uses

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

Uses

In studies of proteasome biology.

Definition

ChEBI: A tripeptide consisting of an Ile-Ile-Thr-NH2 sequence N-substituted on the threonamide amidic nitrogen with a (2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl group and with acetyl and meth l groups on the nitrogen of the isoleucine residue distal to the threonamide; a naturally occurring selective proteasome inhibitor with anti-inflammatory activity.

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.

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.

target

20S proteasome

storage

+4°C

References

1) Meng et al. (1999), Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo anti-inflammatory activity; Proc. Natl. Acad. Sci. USA, 96 10403 2) Hanada et al. (1992), Epoxomicin, a new antitumor agent of microbial origin; J. Antibiot. (Tokyo), 45 1746 3) McNaught et al. (2004), Systemic exposure to proteasome inhibitors causes a progressive model of Parkinson’s disease; Ann. Neurol., 56 149 4) Matsui et al. (2010), Proteasome inhibition in medaka brain induces the features of Parkinson’s disease; J. Neurochem., 115 178 5) Metcalfe et al. (2012), Coordination between proteasome impairment and caspase activation leading to TAU pathology:neuroprotection by cAMP; Cell Death Diff., 3 e326 6) Kordower et al. (2006), Failure of proteasome inhibitor administration to provide a model of Parkinson’s disease in rats and monkeys; Ann. Neurol., 60 264 7) Bove et al. (2006), Proteasome inhibition and Parkinson’s disease modeling; Ann. Neurol., 60 260

EPOXOMICIN Preparation Products And Raw materials

Raw materials

Preparation Products

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EPOXOMICIN Suppliers

China 69 Europe 1 Germany 2 Japan 3 Switzerland 3 United Kingdom 4 United States 22 Global 104

MedChemexpress LLC

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View Lastest Price from EPOXOMICIN manufacturers

Zhuozhou Wenxi import and Export Co., Ltd

Product: Epoxomicin 134381-21-8
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-10

Zhuozhou Wenxi import and Export Co., Ltd

Product: Epoxomicin 134381-21-8
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-09

Career Henan Chemical Co

Product: EPOXOMICIN 134381-21-8
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 1kg-1000kg
Release date: 2020-01-03

134381-21-8, EPOXOMICINRelated Search:

1,6-BIS(CYCLOHEXYLOXIMINOCARBONYLAMINO)HEXANE PF-622 Zafirlukast Ginkgolide B EPOXOMICIN MICROBIAL EPOXOMICIN

BU-4061T

EPOXOMICIN, SYNTHETIC

EPOXOMICIN

(2R)-2-[ACETYL-(N-METHYL-L-ISOLEUCYL)-L-ISOLEUCYL-L-THREONYL-L-LEUCYL]-2-METHYLOXIRANE

n-acetyl-n-methyl-l-isoleucyl-l-isoleucyl-n-[(1s)-3-methyl-1-[[(2r)-2-methyloxiranyl]carbonyl]butyl]-l-threoninamide

Aids010837

Aids-010837

L-Threoninamide, N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]-

Epoxomicin, 99.5%

CS-1626

Epoxomicin(BU-4061T)

EPOXOMICIN;BU4061T;BU-4061T

(2S,3S)-2-[[(2S,3S)-2-[acetyl(Methyl)aMino]-3-Methylpentanoyl]aMino]-N-[(2S,3R)-3-hydroxy-2-[[(2S)-4-Methyl-1-[(2R)-2-Methyloxiran-2-yl]-1-oxopentan-2-yl]aMino]butanoyl]-3-MethylpentanaMide

N-Acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1-[[(2R)-2-methyl-2-oxiranyl]carbonyl]butyl]-L-threoninamide

Epoxomicin, 97%, a selective proteasome inhibitor

BU-4061T,Aids010837

L-Threoninamide, N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1-[[(2R)-2-methyl-2-oxiranyl]carbonyl]butyl]-

134381-21-8 supplier in China

Epoxomicin, 20S proteasome inhibitor

134381-21-8

C28H50N4O7

Enzymes, Inhibitors, and Substrates

Proteasomes

Proteasome, Calpain and Lysosomal Proteases

Inhibitors

BioChemical

Biochemicals and Reagents

Application Index

Cell Signaling Enzymes

peptides

ProteasomeInhibitors