Epoxomicin

Names

[ Name ]:
Epoxomicin

[Synonym ]:
S7038,BU-4061T
Epoxomicin (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
Epoxomicin
N-Acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-{(2S)-4-methyl-1-[(2R)-2-methyl-2-oxiranyl]-1-oxo-2-pentanyl}-L-threoninamide
L-Threoninamide, N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]-

Biological Activity

[Description]:

Epoxomicin is a cell-permeable and irreversible proteasome inhibitor, primarily the chymotrypsin-like activity.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Proteasome

Research Areas >> Cancer

Natural Products >> Others

[References]

[1]. Kim KB, et al. Proteasome inhibition by the natural products epoxomicin and dihydroeponemycin: insights into specificity and potency. Bioorg Med Chem Lett. 1999 Dec 6;9(23):3335-40.

[2]. Hanada M, et al. Epoxomicin, a new antitumor agent of microbial origin. J Antibiot (Tokyo). 1992 Nov;45(11):1746-52.

[3]. Garrett IR, et al. Selective inhibitors of the osteoblast proteasome stimulate bone formation in vivo and in vitro. J Clin Invest. 2003 Jun;111(11):1771-82.

[4]. McNaught KS, et al. Systemic exposure to proteasome inhibitors causes a progressive model of Parkinson's disease. Ann Neurol. 2004 Jul;56(1):149-62.

[5]. Rideout HJ, et al. Dopaminergic neurons in rat ventral midbrain cultures undergo selective apoptosis and form inclusions, but do not up-regulate iHSP70, following proteasomal inhibition. J Neurochem. 2005 Jun;93(5):1304-13.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
795.7±60.0 °C at 760 mmHg

[ Melting Point ]:
107-109ºC

[ Molecular Formula ]:
C₂₈H₅₀N₄O₇

[ Molecular Weight ]:
554.719

[ Flash Point ]:
435.0±32.9 °C

[ Exact Mass ]:
554.367920

[ PSA ]:
157.44000

[ LogP ]:
3.32

[ Vapour Pressure ]:
0.0±6.3 mmHg at 25°C

[ Index of Refraction ]:
1.504

[ Storage condition ]:
-20°C

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

Articles

Intramitochondrial adenylyl cyclase controls the turnover of nuclear-encoded subunits and activity of mammalian complex I of the respiratory chain.

Biochim. Biophys. Acta 1853(1) , 183-91, (2015)

In mammalian cells the nuclear-encoded subunits of complex I are imported into mitochondria, where they are assembled with mt-DNA encoded subunits in the complex, or exchanged with pre-existing copies...

Ataxia telangiectasia mutated (ATM) inhibition transforms human mammary gland epithelial cells.

J. Biol. Chem. 285 , 13092-106, (2010)

Carriers of mutations in the cell cycle checkpoint protein kinase ataxia telangiectasia mutated (ATM), which represent 1-2% of the general population, have an increased risk of breast cancer. However,...

The ubiquitin-proteasome system regulates the stability and activity of the glucose sensor glucokinase in pancreatic β-cells.

Biochem. J. 456(2) , 173-84, (2013)

The ubiquitin-proteasome system is important to maintain pancreatic β-cell function. Inhibition of the proteasome significantly reduced glucose-induced insulin secretion. Key regulators of the stimulu...

Related Compounds

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