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ProductsBack/Epoxomicin [134381-21-8]
Chemical Structure
Chemical Structure
Chemical Structure

Epoxomicin [134381-21-8]

Research Use Only
AG-CN2-0422
AdipoGen Life Sciences
CAS Number134381-21-8
DownloadMSDS
Product group Chemicals
Estimated Purity>97%
Molecular Weight554.7
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Epoxomicin
  • Delivery Days Customer
    10
  • CAS Number
    134381-21-8
  • Certification
    Research Use Only
  • Estimated Purity
    >97%
  • Molecular Formula
    C28H50N4O7
  • Molecular Weight
    554.7
  • Scientific 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 Parkinsons-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 beta5t subunit activity. - Chemical. CAS: 134381-21-8. Formula: C28H50N4O7. MW: 554.7. Synthetic. Antibiotic. Potent anticancer compound. 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). Anti-inflammatory. Antimicrobial and antimalarial. Anti-parasitic. Stimulates bone formation by inhibiting osteoblast proteasome activity. Induces Parkinsons-like symptoms in rats. The ubiquitin-proteasome system (UPS) and autophagy serve as two complementary, reciprocally regulated protein degradation systems. Blockade of UPS by Epoxomicin activates autophagy.
  • 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
  • Storage Instruction
    -20°C,2°C to 8°C
  • UNSPSC
    12352200

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)