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Epoxomicin

AG-CN2-0422-C050 50 µg INQ
AG-CN2-0422-C100 100 µg INQ
AG-CN2-0422-C250 250 µg INQ
AG-CN2-0422-C500 500 µg INQ
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Additional Information

Product Data
Synonyms Antibiotic BU 4061T
Properties
Formula C28H50N4O7
MW 554.7
Merck Index 14: 3630
CAS 134381-21-8
Source/Host Synthetic.
Purity ≥97% (NMR)
Appearance White to off-white solid.
Solubility Soluble in DMSO. Insoluble in water.
InChi Key DOGIDQKFVLKMLQ-JTHVHQAWSA-N
Product Type Chemical
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.
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Product 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

  1. Epoxomicin, a new antitumor agent of microbial origin: M. Hanada, et al.; J. Antibiot. 45, 1746 (1992)
  2. 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)
  3. 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)
  4. Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo antiinflammatory activity: L. Meng, et al.; PNAS 96, 10403 (1999)
  5. 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)
  6. Systemic exposure to proteasome inhibitors causes a progressive model of Parkinson's disease: K.S. McNaught, et al.; Ann. Neurol. 56, 149 (2004)
  7. 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)
  8. The proteasome inhibitor epoxomicin has potent Plasmodium falciparum gametocytocidal activity: B. Czesny, et al.; Antimicrob. Agents Chemother. 53, 4080 (2009)
  9. Evaluation of the in vitro growth-inhibitory effect of epoxomicin on Babesia parasites: M. Aboulaila, et al.; Vet. Parasitol. 167, 19 (2010)
  10. Mechanisms of cross-talk between the ubiquitin-proteasome and autophagy-lysosome systems: V.I. Korolchuk, et al.; FEBS Lett. 584, 1393 (2010)
  11. 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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