See personalized New Product recommendations! Get personalized New Product recommendations! Register or Login for personalized New Product recommendations!

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)

See more

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
Copy SMILES to clipboard
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).

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).

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).

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).

Show all 7 Hide all but first 3
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
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-10. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

Clasto-Lactacystin β-lactone
Lactacystin

Downloads

Batch-specific Information

Login to access batch-specific information

Cayman Chemical is a manufacturer, supplier and vendor of biochemical reagents, assay kits, antibodies, and proteins.

Other Resources
Management Team Company Profile Company History ChemAssistant Tools FAQs Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule Order Terms Browser Recommendation Privacy Statement Site Map

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2012 Cayman Chemical Company

Lost password?