(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
- Molecular Weight:
- 357.41
- MDL Number:
- MFCD07366493
- MOL File:
- 66701-25-5.mol
- MSDS File:
- SDS
| 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) |
| FDA UNII | R76F7856MV |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS08 |
|---|---|
| Signal word | Warning |
| Hazard statements | H371 |
| Precautionary statements | P260-P264-P270-P308+P311-P405-P501 |
| Safety Statements | 22-24/25 |
| WGK Germany | 3 |
| RTECS | RR0390000 |
| F | 10 |
| HS Code | 29252900 |
(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE price More Price(47)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | E3132 | E-64 protease inhibitor | 66701-25-5 | 1mg | $80.5 | 2024-03-01 | Buy |
| Sigma-Aldrich | E3132 | E-64 protease inhibitor | 66701-25-5 | 5mg | $278 | 2024-03-01 | Buy |
| Sigma-Aldrich | E64-RO | E-64 N-[N-(L-3-Trans-carboxirane-2-carbonyl)-L-leucyl]-agmatine | 66701-25-5 | 10mg | $282 | 2024-03-01 | Buy |
| Sigma-Aldrich | E64-RO | E-64 N-[N-(L-3-Trans-carboxirane-2-carbonyl)-L-leucyl]-agmatine | 66701-25-5 | 25mg | $544 | 2024-03-01 | Buy |
| Alfa Aesar | J62933 | E-64 | 66701-25-5 | 5mg | $109.65 | 2024-03-01 | Buy |
(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE Chemical Properties,Uses,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
(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Alpha Biopharmaceuticals Co., Ltd | +86-411-39042497 +8613921981412 | sales@alphabiopharm.com | China | 886 | 58 |
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 32480 | 60 |
| Hubei xin bonus chemical co. LTD | 86-13657291602 | linda@hubeijusheng.com | CHINA | 22968 | 58 |
| BOC Sciences | +1-631-485-4226 | inquiry@bocsci.com | United States | 19553 | 58 |
| Career Henan Chemica Co | +86-0371-86658258 15093356674; | laboratory@coreychem.com | China | 30255 | 58 |
| ANHUI WITOP BIOTECH CO., LTD | +8615255079626 | eric@witopchemical.com | China | 23556 | 58 |
| Dideu Industries Group Limited | +86-29-89586680 +86-15129568250 | 1026@dideu.com | China | 29525 | 58 |
| Henan Alfa Chemical Co., Ltd | +8618339805032 | alfa4@alfachem.cn | China | 12756 | 58 |
| Nextpeptide Inc | +86-0571-81612335 +8613336028439 | sales@nextpeptide.com | China | 19915 | 58 |
| InvivoChem | +1-708-310-1919 +1-13798911105 | sales@invivochem.cn | United States | 6393 | 58 |