A protease inhibitor
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Active Metabolite(s)
10007964E-64c
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E-64d

Item No. 13533

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[[[(1S)-3-methyl-1[[(3S-methylbutyl)amino]carbonyl]butyl]amino]carbonyl]-2S-oxiranecarboxylic acid, ethyl ester
CAS Number
88321-09-9
Synonyms
  • Aloxistatin
  • E-64c ethyl ester
  • EP 453
  • EST
  • Loxistatin
  • NSC 694281
Molecular Formula
C17H30N2O5
Formula Weight
342.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/mlEthanol: 10 mg/ml
SMILES
CCOC([C@@H]1[C@@H](C(N[C@H](C(NCCC(C)C)=O)CC(C)C)=O)O1)=O
InChi Code
InChI=1S/C17H30N2O5/c1-6-23-17(22)14-13(24-14)16(21)19-12(9-11(4)5)15(20)18-8-7-10(2)3/h10-14H,6-9H2,1-5H3,(H,18,20)(H,19,21)/t12-,13-,14-/m0/s1
InChi Key
SRVFFFJZQVENJC-IHRRRGAJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

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    Cayman Chemical
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    Product Description

    E-64d is an irreversible, membrane-permeable inhibitor of lysosomal and cytosolic cysteine proteases and has diverse biological activities.1,2,3,4 It is a synthetic analog of E-64 (Item No. 10007963) and prodrug form of E-64c (Item No. 10007964) that inhibits calpain and the cysteine proteases cathepsins F, -K, -B, -H, and -L.1,5 E-64d (20-200 µM) induces cell cycle arrest at the G2/M phase in A431 human epidermoid carcinoma cells.2 It inhibits protease-resistant prion protein accumulation in scrapie-infected neuroblastoma cells with an IC50 value of 0.5 µM.3 E-46d also inhibits entry of vesicular stomatitis virus (VSV) particles pseudotyped with severe acute respiratory syndrome coronavirus (SARS-CoV) or SARS-CoV-2 spike glycoprotein into Vero cells, an effect that is reduced by expression of the serine protease TMPRSS2.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wilcox, D., and Mason, R.W. Inhibition of cysteine proteinases in lysosomes and whole cells. Biochem. J. 285, 495-502 (1992).

    2. Shoji, Y., Senshu, M., Iwashita, S., et al. Thiol protease-specific inhibitor E-64 arrests human epidermoid carcinoma A431 cells at mitotic metaphase. Proc. Natl. Acad. Sci. USA 85(1), 146-150 (1988).

    3. Doh-Ura, K., Iwaki, T., and Caughey, B. Lysosomotropic agents and cysteine protease inhibitors inhibit scrapie-associated prion protein accumulation. J. Virol. 74(10), 4894-4897 (2000).

    4. Hoffmann, M., Kleine-Weber, H., Schroeder, S., et al. SARS-CoV-2 cell entry depends on ACE2 and TMPRSS2 and is blocked by a clinically proven protease inhibitor. Cell 181(2), 271-280 (2020).

    Product Citations

    Liu, F., Zuo, X., Liu, Y., et al. Suppression of membranous LRP5 recyling, Wnt/β-catenin signaling, and colon carcinogenesis by 15-LOX-1 peroxidation of linoleic acid in PI3P. Cell Rep. 32(7), 108049 (2020).

    Han, H., Chou, C.C., Li, R., et al. Chalcomoracin is a potent anticancer agent acting through triggering oxidative stress via a mitophagy- and paraptosis-dependent mechanism. Sci. Rep. 8(1), 9566 (2018).