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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

E-64

Cayman Chemical Item Number 10007963

(CAS 66701-25-5)

E-64 (CAS 66701-25-5)

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Description

E-64 is a natural, potent, and irreversible inhibitor of cysteine proteases.1 Its IC50 values for inhibiting cathepsins K, S, and L, in vitro, are 1.4, 4.1, and 2.5 nM, respectively.2 E-64 also inhibits papain, calpain, and cathepsins B and H, but not serine proteases (e.g., plasmin, trypsin, tissue kallikrein) or aspartic proteases (e.g., pepsin).3 The mode of action involves the formation of a thioether linkage between E-64 and the thiol group of the protease; E-64 does not react with the functional thiol group of non-protease enzymes (e.g., creatine kinase, L-lactate hydrogenase). While E-64 is usually used in biochemical assays, it can also be used in intact cells at higher (μM) concentrations.4,5,6

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

2 Susa, M., Luong-Nguyen, N., Cappellen, D., et al. Human primary osteoclasts: in vitro generation and applications as pharmacological and clinical assay. J Transl Med 2(6) (2004).

3 Barrett, A.J., Kembhavi, A.A., Brown, M.A., et al. L-trans-Epoxysuccinyl-leucylamido(4-guanidino)butane (E-64) and its analogues as inhibitors of cysteine proteinases including cathepsins B, H and L. Biochem J 201 189-198 (1982).

4 Giusti, I., D'Ascenzo, S., Millimaggi, D., et al. Cathepsin B mediates the pH-dependent proinvasive activity of tumor-shed microvesicles. Neoplasia 10(5) 481-488 (2008).

5 Ahlberg, J., Berkenstam, A., Henell, F., et al. Degradation of short and long lived proteins in isolated rat liver lysosomes; effects of pH, temperature, and proteolytic inhibitors. J Biol Chem 260(9) 5847-5854 (1985).

6 Drew, M.E., Banerjee, R., Uffman, E.W., et al. Plasmodium food vacuole plasmepsins are activated by falcipains. J Biol Chem 283(19) 12870-12876 (2008).

Formal Name 3-​[[[(1S)-​1-​[[[4-​[(aminoiminomethyl)amino]butyl]amino]carbonyl]-​3-​methylbutyl]amino]carbonyl]-​(2S,​3S)-​oxiranecarboxylic acid
CAS Number 66701-25-5
Molecular Formula C15H27N5O5
Formula Weight 357.4
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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NC(=N)​NCCCCNC(=O)​[C@H]​(CC(C)​C)​NC(=O)​[C@H]​1O[C@@H]​1C(=O)​O

Background Reading

Drew, M.E., Banerjee, R., Uffman, E.W., et al. Plasmodium food vacuole plasmepsins are activated by falcipains. J Biol Chem 283(19) 12870-12876 (2008).

Ahlberg, J., Berkenstam, A., Henell, F., et al. Degradation of short and long lived proteins in isolated rat liver lysosomes; effects of pH, temperature, and proteolytic inhibitors. J Biol Chem 260(9) 5847-5854 (1985).

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

Susa, M., Luong-Nguyen, N., Cappellen, D., et al. Human primary osteoclasts: in vitro generation and applications as pharmacological and clinical assay. J Transl Med 2(6) (2004).

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).

Barrett, A.J., Kembhavi, A.A., Brown, M.A., et al. L-trans-Epoxysuccinyl-leucylamido(4-guanidino)butane (E-64) and its analogues as inhibitors of cysteine proteinases including cathepsins B, H and L. Biochem J 201 189-198 (1982).

Giusti, I., D'Ascenzo, S., Millimaggi, D., et al. Cathepsin B mediates the pH-dependent proinvasive activity of tumor-shed microvesicles. Neoplasia 10(5) 481-488 (2008).

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Size Price Quantity Subtotal
1 mg $16.00 $0.00
5 mg $72.00 $0.00
10 mg $128.00 $0.00
25 mg $280.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-02-11. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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