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E3132

Sigma-Aldrich

E-64

protease inhibitor

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Synonym(s):
trans-Epoxysuccinyl-L-leucylamido(4-guanidino)butane, L-trans-3-Carboxyoxiran-2-carbonyl-L-leucylagmatine, N-(trans-Epoxysuccinyl)-L-leucine 4-guanidinobutylamide
Empirical Formula (Hill Notation):
C15H27N5O5
CAS Number:
Molecular Weight:
357.41
Beilstein:
1405664
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

Assay

≥98% (HPLC)

form

powder

solubility

water: 20 mg/mL, clear, colorless to faintly yellow

storage temp.

2-8°C

SMILES string

CC(C)C[C@H](NC(=O)[C@@H]1O[C@H]1C(O)=O)C(=O)NCCCCNC(N)=N

InChI

1S/C15H27N5O5/c1-8(2)7-9(20-13(22)10-11(25-10)14(23)24)12(21)18-5-3-4-6-19-15(16)17/h8-11H,3-7H2,1-2H3,(H,18,21)(H,20,22)(H,23,24)(H4,16,17,19)/t9-,10+,11+/m0/s1

InChI key

LTLYEAJONXGNFG-HBNTYKKESA-N

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This Item
E8640324890E64-RO
E-64 protease inhibitor

E3132

E-64

E-64d protease inhibitor

E8640

E-64d

E-64 Protease Inhibitor The E-64 Protease Inhibitor, also referenced under CAS 66701-25-5, controls the biological activity of E-64 Protease. This small molecule/inhibitor is primarily used for Protease Inhibitors applications.

324890

E-64 Protease Inhibitor

E-64 N-[N-(L-3-Trans-carboxirane-2-carbonyl)-L-leucyl]-agmatine

E64-RO

E-64

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

-

biological source

-

Quality Level

300

Quality Level

200

Quality Level

200

Quality Level

100

form

powder

form

powder

form

solid

form

powder

solubility

water: 20 mg/mL, clear, colorless to faintly yellow

solubility

methanol: water (1:1): 5 mg/mL, clear, colorless

solubility

water: 20 mg/mL, DMSO: 25 mg/mL

solubility

ethanol: water (1:1): soluble 20 mg/mL

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

General description

E-64 is a cysteine protease inhibitor that was isolated from the mold Aspergillus japonicus TPR-64. E-64 is also known as N-[N-(L-3-trans-carboxyoxiran-2-carbonyl)-L-leucyl]-agmatine. E-64 effectively inhibits various cysteine proteases, in particular:
  • cathepsin K
  • cathepsin L
  • cathepsin S
E-64 also acts against other enzymes, such as:
  • calpain
  • cathepsin B
  • cathepsin H
  • papain

Application

E-64 is an effective ligand for affinity purification of cysteine proteases. When coupled to a thiolated affinity matrix, binding is no longer irreversible, but specificity is retained.

Biochem/physiol Actions

E-64 is an irreversible, potent, and highly selective cysteine protease inhibitor. E-64 does not react with the functional thiol group of non-protease enzymes, such as L-lactate dehydrogenase or creatine kinase. E-64 will not inhibit serine proteases (except trypsin) like other cysteine protease inhibitors, leupeptin and antipain. The trans-epoxysuccinyl group (active moiety) of E-64 irreversibly binds to an active thiol group in many cysteine proteases, such as papain, actinidase, and cathepsins B, H, and L to form a thioether linkage. E-64 is a very useful cysteine protease inhibitor for use in in vivo studies because it has a specific inhibition, it is permeable in cells and tissues and has low toxicity.

Preparation Note

E-64 is soluble in water. A 20 mg/ml solution can be prepared in water (heat may be needed). A suggested stock solution is a 1 mM aqueous solution. The effective concentration for use as a protease inhibitor is 1 to10 μM. Aqueous stock solutions are stable for months at -20 °C. Diluted solutions are stable for days at neutral pH. E-64 is stable from pH 2-10, but is unstable in ammonia or in HCl. E-64 is also soluble in DMSO, a 10 mM solution can be prepared in dry DMSO and stored at -20 °C. Subsequent dilutions were in culture medium. Solutions for injection were prepared by dissolving E-64 in 0.9% sodium chloride or in a minimum amount of saturated sodium bicarbonate followed by dilution with 0.9% sodium chloride (after adjusting the pH to 7.0 with acetic acid).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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