(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
(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)
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..…
N-Bromosuccinimide Price
- Product number
- E3132
- Product name
- E-64
- Purity
- protease inhibitor
- Packaging
- 1mg
- Price
- $80.5
- Updated
- 2024/03/01
- Product number
- E3132
- Product name
- E-64
- Purity
- protease inhibitor
- Packaging
- 5mg
- Price
- $278
- Updated
- 2024/03/01
- 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
- 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
- Product number
- J62933
- Product name
- E-64
- Packaging
- 5mg
- Price
- $109.65
- Updated
- 2024/03/01
(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
- 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
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