Epoxomicin

Specifications / Handling

More Information
Product Details
Synonyms	Antibiotic BU 4061T
Product Type	Chemical
Properties
Formula	C₂₈H₅₀N₄O₇
MW	554.7
Merck Index	14: 3630
CAS	134381-21-8
Source/Host Chemicals	Synthetic.
Purity Chemicals	≥97% (HPLC)
Appearance	White to off-white solid.
Solubility	Soluble in DMSO. Insoluble in water.
Identity	Determined by ¹H-NMR.
InChi Key	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
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry. Protect from light and moisture.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Antibiotic [1].
Potent anticancer compound [1, 7].
Cell permeable, potent, selective and irreversible 20S proteasome inhibitor. Predominantly inhibits the chymotrypsin-like (CTRL) activity of the proteasome. Exhibits lower level inhibition of proteasome trypsin-like and caspase-like activitives (100 and 1,000-fold slower rates respectively) [2, 3].
Anti-inflammatory [4].
Antimicrobial and antimalarial [8].
Anti-parasitic [9].
Stimulates bone formation by inhibiting osteoblast proteasome activity [5].
Induces Parkinson's-like symptoms in rats [6].
The ubiquitin-proteasome system (UPS) and autophagy serve as two complementary, reciprocally regulated protein degradation systems. Blockade of UPS by Epoxomicin activates autophagy.
Blocks the Thymoproteasome β5t subunit activity.

Product References

Epoxomicin, a new antitumor agent of microbial origin: M. Hanada, et al.; J. Antibiot. 45, 1746 (1992)
Total synthesis of the potent proteasome inhibitor epoxomicin: a useful tool for understanding proteasome biology: N. Sin, et al.; Bioorg. Med. Chem. Lett. 9, 2283 (1999)
Proteasome inhibition by the natural products epoxomicin and dihydroeponemycin: insights into specificity and potency: K.B. Kim, et al.; Bioorg. Med. Chem. Lett. 9, 3335 (1999)
Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo antiinflammatory activity: L. Meng, et al.; PNAS 96, 10403 (1999)
Selective inhibitors of the osteoblast proteasome stimulate bone formation in vivo and in vitro: I.R. Garrett, et al.; J. Clin. Invest. 111, 1771 (2003)
Systemic exposure to proteasome inhibitors causes a progressive model of Parkinson's disease: K.S. McNaught, et al.; Ann. Neurol. 56, 149 (2004)
Establishment and some characteristics of epoxomicin (a proteasome inhibitor) resistant variants of the human squamous cell carcinoma cell line, A431: K. Ohkawa, et al.; Int. J. Oncol. 24, 425 (2004)
The proteasome inhibitor epoxomicin has potent Plasmodium falciparum gametocytocidal activity: B. Czesny, et al.; Antimicrob. Agents Chemother. 53, 4080 (2009)
Evaluation of the in vitro growth-inhibitory effect of epoxomicin on Babesia parasites: M. Aboulaila, et al.; Vet. Parasitol. 167, 19 (2010)
Mechanisms of cross-talk between the ubiquitin-proteasome and autophagy-lysosome systems: V.I. Korolchuk, et al.; FEBS Lett. 584, 1393 (2010)
Activity-Based Profiling Reveals Reactivity of the Murine Thymoproteasome-Specific Subunit β5t: B.I. Florea, et al.; Chem. Biol. 17, 795 (2010)

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