| Identification | More | [Name]
(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE | [CAS]
66701-25-5 | [Synonyms]
(2S, 3S)-TRANS-EPOXY SUCCINYL-L-LEUCYLAMIDO-(4-GUANIDINO) BUTANE
E-64
E-64 HEMIHYDRATE
E-64 PROTEASE INHIBITOR
EPOXYSUCCINYL-L-LEUCYLAMIDO-(4-GUANIDINO)BUTANE
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
L-TRANS-3-CARBOXYOXIRAN-2-CARBONYL-L-LEUCYLAGMATINE
L-TRANS-EPOXYSUCCINYL-LEU-4-GUANIDINOBUTYLAMIDE
L-TRANS-EPOXYSUCCINYL-LEU-AGMATINE
L-TRANS-EPOXYSUCCINYL-LEUCYLAMIDE-(4-GUANIDO)-BUTANE
N-[N-(L-3-TRANS-CARBOXIRANE-2-CARBONYL)-L-LEUCYL]-AGMATINE
N-[N-(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL]-L-LEUCYL)-AGMATINE
N-(TRANS-EPOXYSUCCINYL)-L-LEUCINE 4-GUANIDINOBUTYLAMIDE
TRANS-3-CARBOXYOXIRANE-2-CARBONYL-L-LEUCYLAGMATINE
TRANS-EPOXYSUCCINYL-LEUCYLAMIDO-[4-GUANIDINO]BUTANE
TRANS-EPOXYSUCCINYL-L-LEUCYL-AMIDO(4-GUANDINO)BUTANE | [EINECS(EC#)]
613-978-4 | [Molecular Formula]
C30H56N10O11 | [MDL Number]
MFCD07366493 | [Molecular Weight]
732.83 | [MOL File]
66701-25-5.mol |
| Chemical Properties | Back Directory | [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
| [form ]
White solid | [pka]
3.16±0.40(Predicted) | [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. Solutions in 1 | [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) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
RR0390000
| [F ]
10 | [HS Code ]
29252900 |
| Hazard Information | Back Directory | [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 2-8°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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