(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE

Product Name: (L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE
CAS No.: 66701-25-5
Chemical Name: (L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE
Synonyms: E-64;CS-1623;E-64 HCl;E64;E-64;E 64;E-64 HEMIHYDRATE;E-64 research grade;E-64 solution (10mM);thiolproteaseinhibitor;proteinaseinhibitore64;E-64 PROTEASE INHIBITOR
CBNumber: CB3667057
Molecular Formula: C15H27N5O5
Formula Weight: 357.41
MOL File: 66701-25-5.mol

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(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE Property

Melting point:: >170°C (dec.)
Density: 1.44±0.1 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: H₂O: 20 mg/mL, clear, colorless
pka: 3.16±0.40(Predicted)
form: White solid
color: White or off-white
Water Solubility: Soluble in DMSO (25mg/ml), or water (20mg/ml)
Sensitive: Light Sensitive
BRN: 1405664
Stability:: Stable for 1 year from date of purchase as supplied.
InChIKey: LTLYEAJONXGNFG-DCAQKATOSA-N
SMILES: O1[C@H](C(N[C@H](C(NCCCCNC(N)=N)=O)CC(C)C)=O)[C@H]1C(O)=O
CAS DataBase Reference: 66701-25-5(CAS DataBase Reference)

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Safety

Safety Statements: 22-24/25
WGK Germany: 3
RTECS: RR0390000
F: 10
HS Code: 29252900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H371May cause damage to organs

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: E3132
Product name: E-64
Purity: protease inhibitor
Packaging: 1mg
Price: $80.5
Updated: 2024/03/01

Sigma-Aldrich

Product number: E3132
Product name: E-64
Purity: protease inhibitor
Packaging: 5mg
Price: $278
Updated: 2024/03/01

Sigma-Aldrich

Product number: E64-RO
Product name: E-64
Purity: N-[N-(L-3-Trans-carboxirane-2-carbonyl)-L-leucyl]-agmatine
Packaging: 10mg
Price: $282
Updated: 2024/03/01

Sigma-Aldrich

Product number: E64-RO
Product name: E-64
Purity: N-[N-(L-3-Trans-carboxirane-2-carbonyl)-L-leucyl]-agmatine
Packaging: 25mg
Price: $544
Updated: 2024/03/01

Alfa Aesar

Product number: J62933
Product name: E-64
Packaging: 5mg
Price: $109.65
Updated: 2024/03/01

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(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE Chemical Properties,Usage,Production

Description

E-64 (66701-25-5) is a cell-permeable, epoxysuccinyl peptide irreversible inhibitor of calpain and other cysteine proteases.1,2?Inhibits calpain-dependent apoptosis pathway in T cells3?but promotes heat-induced apoptosis in FM3A cells. Typical working concentration is 0.5-10 μg/ml.4

Uses

It is used as a broad spectrum cysteine proteinase and calpain activation inhibitor. Additionally, Prevotella intermediate studies report that E-64 blocks the breakdown of methaemoglobin and the oxidation of oxyhaemoglobin by InpA. E-64 has also been used to study excystation in Giardia lamblia. E-64 is an inhibitor of Calpain, cathepsin K and cathepsin S. 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

Definition

ChEBI: E64 is an epoxy monocarboxylic acid, a dicarboxylic acid monoamide, a member of guanidines and a L-leucine derivative. It has a role as a protease inhibitor, an antimalarial and an antiparasitic agent. It is a tautomer of an E64 zwitterion.

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

Hazard

A reproductive hazard.

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.

storage

Store at -20°C

References

1) Wang and Yuen (1994),?Calpain inhibition: an overview of its therapeutic potential; Trends Pharmacol. Sci.,?15?412 2) Barrett?et al.?(1982),?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 3) Sarin?et al.?(1994),?Inhibition of activation-induced programmed cell death and restoration of defective immune responses of HIV+ donors by cysteine protease inhibitors; J. Immunol.,?153?862 4) Zhu?et al.?(1996),?Promotion of heat-induced apoptosis in FM3A cells by protease inhibitors; Biochem. Biophys. Res. Commun.,?225?924

(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE Preparation Products And Raw materials

Raw materials

Preparation Products

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(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE Suppliers

China 165 France 1 Germany 5 India 3 Japan 3 Switzerland 2 Ukraine 1 United Kingdom 8 United States 37 Global 225

Tocris Bioscience

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66701-25-5, (L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATERelated Search:

3,4-DICHLOROISOCOUMARIN ACTINONIN glutamyl-glycyl-arginine chloromethyl ketone Everolimus Bestatin Pepstatin Trametinib 4-(2-Aminoethyl)benzenesulfonylfluoride hydrochloride Z-VAD-FMK TRANS-2,3-EPOXYBUTANE (R)-(-)-AMINO-3-HYDROXYBUTANOIC ACID GLYCIDAMIDE (L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE 2-Hydroxy-4-amino butanoic acid (2-amino-2-oxoethoxy)acetic acid 2(2-HYDROXYETHOXY)ACETAMIDE (2-AMINO-ETHOXY)-ACETIC ACID EP 459

(2S,3S)-3-(((S)-1-((4-Guanidinobutyl)amino)-4-methyl-1-oxopentan-2-yl)carbamoyl)oxirane-2-carboxylic acid

(2S,3S)-3-(((S)-1-((4-Guanidinobutyl)amino)-4-methyl-1-oxopentan-2-yl)carbamoyl)oxirane-2-carb

oxiranecarboxylicacid,3-(((1-(((4-((aminoiminomethyl)amino)butyl)amino)carbon

proteinaseinhibitore64

thiolproteaseinhibitor

TRANS-EPOXYSUCCINYL-L-LEUCYLAMIDO-*(4-GU ANIDINO)BUT

(2S, 3S)-TRANS-EPOXY SUCCINYL-L-LEUCYLAMIDO-(4-GUANIDINO) BUTANE

L-TRANS-3-CARBOXYOXIRAN-2-CARBONYL-L-LEUCYLAGMATINE

L-TRANS-EPOXYSUCCINYL-LEU-4-GUANIDINOBUTYLAMIDE

L-TRANS-EPOXYSUCCINYL-LEU-AGMATINE

(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE (E-64)

E-64, L-trans-Epoxysuccinyl-Leu-agMatine

2-Oxiranecarboxylic acid, 3-[[[(1S)-1-[[[4-[(aMinoiMinoMethyl)aMino]butyl]aMino]carbonyl]-3-Methylbutyl]aMino]carbonyl]-, (2S,3S)-

L-TRANS-EPOXYSUCCINYL-LEUCYLAMIDE-(4-GUANIDO)-BUTANE

TRANS-EPOXYSUCCINYL-LEUCYLAMIDO-[4-GUANIDINO]BUTANE

TRANS-EPOXYSUCCINYL-L-LEUCYL-AMIDO(4-GUANDINO)BUTANE

TRANS-EPOXYSUCCINYL-L-LEUCYLAMIDO-(4-GUANIDINO)BUTANE

TRANS-3-CARBOXYOXIRANE-2-CARBONYL-L-LEUCYLAGMATINE

(2s-(2-alpha,3-beta(r*)))-yl)-3-methylbutyl)amino)carbonyl)

e64(proteinaseinhibitor)

3-[[[(1S)-1-[[[4-[(aminoiminomethyl)amino]butyl]amino]carbonyl]-3-methylbutyl]amino]carbonyl]-(2S,3S)-oxiranecarboxylic acid

trans-Epoxysuccinyl-L-leucylaMido(4-guanidino)butane, L-trans-3-Carboxyoxiran-2-carbonyl-L-leucylagMatine, N-(trans-Epoxysuccinyl)-L-leucine 4-guanidinobutylaMide

(2S,3S)-3-(((S)-1-((4-Guanidinobutyl)amino)-4-methyl-1-oxopentan-2-yl)carbamoyl)oxirane-2-carboxy

EPOXYSUCCINYL-L-LEUCYLAMIDO-(4-GUANIDINO)BUTANE

E-64 HEMIHYDRATE

E-64 PROTEASE INHIBITOR

E-64

EXPOXY[L-3-TRANS-CARBOXYOXIRAN-2-CARBONYL]-L-LEU-AGMATIN

[L-3-TRANS-CARBOXY-OXIRAN-2-CARBONYL]-LEU-AGMATIN

(L-3-TRANS-CARBOXYOXIRAN-2-CARBONYL)-L-LEUCYL-AGMATIN

(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYL-AGMATINE

(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE

N-(TRANS-EPOXYSUCCINYL)-L-LEUCINE 4-GUANIDINOBUTYLAMIDE

N-[N-(L-3-TRANS-CARBOXIRANE-2-CARBONYL)-L-LEUCYL]-AGMATINE

N-[N-(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL]-L-LEUCYL)-AGMATINE

E-64 research grade

CS-1623

E64;E-64;E 64

E-64 Protease Inhibitor - CAS 66701-25-5 - Calbiochem

(2S,3S)-3-[[[(1S)-1-[[[4-(Aminoiminomethyl)amino]butyl]amino]carbonyl]-3-methylbutyl]amino]carbonyl]-2-oxiranecarboxylic acid

(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE USP/EP/BP

E-64 HCl

3-[[1-[4-(diaminomethylideneamino)butylamino]-4-methyl-1-oxopentan-2-yl]carbamoyl]oxirane-2-carboxylic acid

Cathepsin,Inhibitor,Proteinase inhibitor E-64,inhibit,Proteinase inhibitor E64,E-64,Bacterial,Autophagy

E-64 solution (10mM)

66701-25-5

C15H27N5O5

Biochemicals and Reagents

BioChemical

A to C

Organic Covalent Modifiers

Enzyme Inhibitors

Enzyme Inhibitors by Type

Enzyme Inhibitors by Enzyme

Enzymes, Inhibitors, and Substrates

Pepetides

ProteaseInhibitors

Inhibitors