E-64

SIGMA/E3132 - protease inhibitor

Synonym: trans-Epoxysuccinyl-L-leucylamido(4-guanidino)butane; L-trans-3-Carboxyoxiran-2-carbonyl-L-leucylagmatine; N-(trans-Epoxysuccinyl)-L-leucine 4-guanidinobutylamide

CAS Number: 66701-25-5
Empirical Formula (Hill Notation): C₁₅H₂₇N₅O₅
Molecular Weight: 357.41
MDL Number: MFCD00080261
Linear Formula: C₁₅H₂₇N₅O₅
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-E3132-1MG	1 mg	$88.70 1/EA	Add To Favorites
45-E3132-5MG	5 mg	$307.00 1/EA	Add To Favorites
45-E3132-10MG	10 mg	$458.00 1/EA	Add To Favorites
45-E3132-25MG	25 mg	$1150.00 1/EA	Add To Favorites
45-E3132-50MG	50 mg	$1590.00 1/EA	Add To Favorites

This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: E3132-10MG

Properties
Descriptions
Safety Info.
Basic Data

assay	≥98% (HPLC)
biological source	synthetic (organic)
form	powder
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
Quality Level	300
SMILES string	CC(C)C[C@H](NC(=O)[C@@H]1O[C@H]1C(O)=O)C(=O)NCCCCNC(N)=N
solubility	water: 20 mg/mL, clear, colorless to faintly yellow
storage temp.	2-8°C

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.
Biochem/physiol Actions:	Effective irreversible inhibitor of cysteine proteases that does not affect cysteine residues in other enzymes or react with low molecular weight thiols such as calpain and cathepsin B. Effective concentration 1-10 μM.
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
Packaging:	1, 5, 10 mg in glass bottle
Packaging:	25, 50 mg in poly bottle
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).

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥98% (HPLC)
Storage Temp.	2-8°C
UNSPSC	12352202

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