ChemicalBook > CAS DataBase List > (L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE

(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

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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