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E-64c

Cayman Chemical Item Number 10007964

EP 475; Loxistatin Acid; NSC 694279 (CAS 76684-89-4)

E-64c (CAS 76684-89-4)

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Description

Cysteine proteases are a class of enzymes containing an active-site cysteine residue that are important in protein degradation pathways. E-64c is a synthetic analog of E-64, a potent and irreversible cysteine protease inhibitor isolated from Aspergillus japonicus.1 E-64c inhibits the cysteine proteases cathepsin B and cathepsin L from rat liver with IC50 values of 8.7 and 3.5 nM, respectively.2 The ethyl ester of E-64c, E-64d, is cell permeable and hydrolyzed in cell culture to E-64c. E-64d arrests the growth of A431 cells in metaphase at concentrations between 20-200 µg/ml.2

1 Drahl, C., Cravatt, B.F., and Sorensen, E.J. Protein-reactive natural products. Angew Chem Int Ed 44 5788-5809 (2005).

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 85 146-150 (1988).

Synonyms
  • EP 475
  • Loxistatin Acid
  • NSC 694279
Formal Name (2S,​3S)-​3[[(1S)-​3-​methyl-​1-​[[(3-​methylbutyl)amino]carbonyl]butyl]amino]carbonyl]-​oxiranecarboxylic acid
CAS Number 76684-89-4
Molecular Formula C15H26N2O5
Formula Weight 314.4
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CC(C)​CCN[C@H]​(=O)​[C@H]​(CC(C)​C)​NC(=O)​C1OC1C(=O)​O

Background Reading

Drahl, C., Cravatt, B.F., and Sorensen, E.J. Protein-reactive natural products. Angew Chem Int Ed 44 5788-5809 (2005).

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 85 146-150 (1988).

Sarabia, F., Sánchez-Ruiz, A., and Chammaa, S. Steroselective synthesis of E-64 and related cysteine proteases inhibitors from 2,3-epoxyamides. Bioorg Med Chem 13 1691-1705 (2005).
Size Price Quantity Subtotal
1 mg $49.00 $0.00
5 mg $221.00 $0.00
10 mg $392.00 $0.00
25 mg $858.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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