| Identification | Back Directory | [Name]
EPOXOMICIN | [CAS]
134381-21-8 | [Synonyms]
CS-1626
BU-4061T
EPOXOMICIN
Aids010837
Aids-010837
Epoxomicin, 99.5%
BU-4061T,Aids010837
Epoxomicin(BU-4061T)
EPOXOMICIN, SYNTHETIC
EPOXOMICIN;BU4061T;BU-4061T
134381-21-8 supplier in China
Epoxomicin, 97%, a selective proteasome inhibitor
(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
L-Threoninamide, N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]-
N-Acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1-[[(2R)-2-methyl-2-oxiranyl]carbonyl]butyl]-L-threoninamide
L-Threoninamide, N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1-[[(2R)-2-methyl-2-oxiranyl]carbonyl]butyl]-
(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 | [Molecular Formula]
C28H50N4O7 | [MDL Number]
MFCD00909008 | [MOL File]
134381-21-8.mol | [Molecular Weight]
554.72 |
| Chemical Properties | Back Directory | [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). | [form ]
solid
| [pka]
13.02±0.46(Predicted) | [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 | [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 |
| Hazard Information | Back Directory | [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]
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]
Store at -20°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 |
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Sigma-Aldrich
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Jinan Putubio Tech Co., Ltd.
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