(L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE
Synonym(s):E-64;N-(trans-Epoxysuccinyl)-L -leucine 4-guanidinobutylamide;n-[n-( l-transepoxysuccinic acid)-l-leucyl]-agmatine;n-[n-(l-3-trans-carboxirane-2-carbonyl)-l-leucyl]-4-aminobutylguanidine;L -trans-3-Carboxyoxiran-2-carbonyl-L -leucylagmatine
- CAS NO.:66701-25-5
- Empirical Formula: C15H27N5O5
- Molecular Weight: 357.41
- MDL number: MFCD07366493
- EINECS: 613-978-4
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-01-26 15:56:31
What is (L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE?
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
The Uses of (L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE
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
What are the applications of Application
E-64 is an irreversible, potent, and highly selective broad spectrum cysteine proteinase and calpain activation inhibitor.
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
Properties of (L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE
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. |
CAS DataBase Reference | 66701-25-5(CAS DataBase Reference) |
Safety information for (L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE
Signal word | Warning |
Pictogram(s) |
Health Hazard GHS08 |
GHS Hazard Statements |
H371:Specific target organ toxicity, single exposure |
Precautionary Statement Codes |
P260:Do not breathe dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P405:Store locked up. P501:Dispose of contents/container to..… |
Computed Descriptors for (L-3-TRANS-CARBOXYOXIRANE-2-CARBONYL)-L-LEUCYLAGMATINE HEMIHYDRATE
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 |
New Products
Tubulysin H Tubulysin I Tubulysin A 4-CYANO-TETRAHYDROPYRAN-4-CARBOXYLIC ACID 4,4-DIFLUOROPIPERIDINE 2,2-Difluoropropanol 3-Aminocyclobutanone hydrochloride CYCLOBUTYLAMINE HYDROCHLORIDE 4-(Benzyloxy)-3-bromophenylacetic Acid (1R,2S)-2-(3,4-Difluorophenyl)cyclopropanamine Calcium Sodium Phosphosilicate IH 2-(1-(Mercaptomethyl) cyclopropyl) acetonitrile 2-[2-[3(S)-3[2-(7-chloro-2-quinolinyl) ethenyl] phenyl-3- hydroxyl propyl] phenyl]-2-propanol 2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol ethanedioate Fuel shell 2-(2,3-Dihydro- benzofuran-5-yl)-1- morpholin-4-yl- ethanethione 5-Piperazin-1-yl- benzofuran-2- carboxylic acid ethyl ester. HCl Latanoprostene Bunod Magnesium Trisilicate Lubiprostone Flame Retardant Zinc Borate 7-Methoxyquinoline-4-carbonitrile 1H-Imidazole-4-carbonitrile 7-Methoxyquinoline-4-carboxylic acidRelated products of tetrahydrofuran
You may like
-
E-64, protease inhibitor CAS 66701-25-5View Details
66701-25-5 -
E-64 CAS 66701-25-5View Details
66701-25-5 -
E-64 Protease Inhibitor CAS 66701-25-5View Details
66701-25-5 -
E-64 CAS 66701-25-5View Details
66701-25-5 -
4,6-dichloro-2-propylthiopyrimidine-5-amine 145783-15-9 98%View Details
145783-15-9 -
151767-02-1 Montelukast Sodium IP/USP 98%View Details
151767-02-1 -
Valacyclovir Hydrochloride IH 98%View Details
124832-27-5 -
2-[2-[3(S)-3[2-(7-chloro-2-quinolinyl) ethenyl] phenyl-3- hydroxyl propyl] phenyl]-2-propanol 98%View Details
142569-70-8