| Identification | Back Directory | [Name]
EST | [CAS]
88321-09-9 | [Synonyms]
EST
E-64D
ep453
Estate
CS-1622
NSC694281
oxistatin
E64d,E-64d
LOXASTATIN
LOXISTATIN
NSC-694281
NSC 694281
aloxistatin
Aloxistatin (E64d
E64c ethyl ester)
E64d, NSC-694281)
Aloxistatin(E-64d)
E-64-D(LOXISTATINE)
E 64d (Aloxistatin)
Aloxistatin (Loxistatin
E-64d [for Biochemical Research]
EST - CAS 88321-09-9 - Calbiochem
Aloxistatin (E-64d) EST Loxistatin
COT (30-397), active, GST tagged human
L-trans-Epoxysuccinyl(OEt)-Leu-3-methylbuty
(2S,3S)-trans-epoxysuccinyl-L-*leucylamido-3-meth
L-TRANS-EPOXYSUCCINYL(OET)-LEU-3-METHYLBUTYLAMIDE
ethylester,(2s-(2-alpha,3-beta(r*)))-mino)carbonyl)
trans-epoxysuccinyl-L-leucylamido 3-methylbutane ethyl
L-TRANS-EPOXYSUCCINYL-LEU-3-METHYLBUTYLAMIDE-ETHYL ESTER
E-64(Trans-Epoxysuccinyl-L-Leucylamido-(4-Guanidino)Butane)
(2S,3S)-ETHYL-TRANS-EPOXYSUCCINYL-L-LEUCYLAMIDO-3-METHYLBUTANE
(2S,3S)-TRANS-EPOXYSUCCINYL-L-LEUCYLAMIDO-3-METHYLBUTANE ETHYL ESTER
Aloxistatin, 98%, irreversible cell-permeable cysteine protease inhibitor
(2S,3S)-trans-Epoxysuccinyl-L-leucylaMido-3-Methylbutane ethyl ester, EST
(L-3TRANS-ETHOXYCARBONYLOXIRANE-2-CARBONYL)-L-LEUCINE-(3-METHYLBUTYL)AMIDE
EST, (2S,3S)-trans-Epoxysuccinyl-L-leucylamido-3-methylbutane ethyl ester
E-64d, L-trans-Epoxysuccinyl(OEt)-Leu-3-MethylbutylaMide, EP453, Aloxistatin, Loxistatin
ALOXISTATIN;E64D;E 64D;LOXISTATIN;E-64C ETHYL ESTER;EP 453;NSC 694281;NSC694281;NSC-694281
(2S,3S)-3-[[[(1S)-3-Methyl-1-[[(3-methylbutyl)amino]carbonyl]-butyl]amino]carbonyl]-2-oxiranec
(2S,3S)-ethyl 3-(((S)-1-(isopentylaMino)-4-Methyl-1-oxopentan-2-yl)carbaMoyl)oxirane-2-carboxylate
Ethyl (2S,3S)-3-[[(2S)-4-Methyl-1-[(3-methylbutyl)amino]-1-oxo-2-pentanyl]carbamoyl]-2-oxiranecarboxylate
[2S,3S,(+)]-3β-[(S)-3-Methyl-1-(3-methylbutylcarbamoyl)butylcarbamoyl]-2α-oxiranecarboxylic acid ethyl ester
3-[[[(1S)-3-methyl-1[[(3S-methylbutyl)amino]carbonyl]butyl]amino]carbonyl]-2S-oxiranecarboxylic acid, ethyl ester
(2S,3S)-3-[[(2S)-4-Methyl-1-[(3-methylbutyl)amino]-1-oxo-2-pentanyl]carbamoyl]-2-oxiranecarboxylic Acid Ethyl Ester
(2S)-3β-[[[(S)-3-Methyl-1-[[(3-methylbutyl)amino]carbonyl]butyl]amino]carbonyl]oxirane-2α-carboxylic acid ethyl ester
(2S,3S)-3-[[[(1S)-3-Methyl-1-[[(3-Methylbutyl)aMino]carbonyl]butyl]aMino]carbonyl]-2-oxiranecarboxylic acid ethyl ester
2-Oxiranecarboxylicacid,3-[[[(1S)-3-methyl-1-[[(3-methylbutyl)amino]carbonyl]butyl]amino]carbonyl]-,ethyl ester, (2S,3S)- | [Molecular Formula]
C17H30N2O5 | [MDL Number]
MFCD00132883 | [MOL File]
88321-09-9.mol | [Molecular Weight]
342.43 |
| Chemical Properties | Back Directory | [Melting point ]
126.2°C | [Boiling point ]
477.88°C (rough estimate) | [density ]
1.0657 (rough estimate) | [refractive index ]
1.5800 (estimate) | [storage temp. ]
−20°C
| [solubility ]
Soluble in DMSO, DMF or ethanol | [form ]
White solid | [pka]
13.32±0.40(Predicted) | [color ]
Fine needles from EtOH | [biological source]
synthetic (organic) | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. |
| Hazard Information | Back Directory | [Description]
E-64d is an irreversible, membrane-permeable inhibitor of lysosomal and cytosolic cysteine proteases and has diverse biological activities.1,2,3,4 It is a synthetic analog of E-64 (Item No. 10007963) and prodrug form of E-64c (Item No. 10007964) that inhibits calpain and the cysteine proteases cathepsins F, -K, -B, -H, and -L.1,5 E-64d (20-200 μM) induces cell cycle arrest at the G2/M phase in A431 human epidermoid carcinoma cells.2 It inhibits protease-resistant prion protein accumulation in scrapie-infected neuroblastoma cells with an IC50 value of 0.5 μM.3 E-46d also inhibits entry of vesicular stomatitis virus (VSV) particles pseudotyped with severe acute respiratory syndrome coronavirus (SARS-CoV) or SARS-CoV-2 spike glycoprotein into Vero cells, an effect that is reduced by expression of the serine protease TMPRSS2.4 | [Uses]
E-64d is an inhibitor of cathepsins B and L as well as a potential inhibitor of calpain. E-64d has been shown to inhibit lysosomal proteases. E-64d has been used in combination with Prepstatin A to in
terfere with autolysosomal digestion. E-64d displays neurovascular and neuronal protective effects after focal cerebral ischemia in rats. | [Definition]
ChEBI: An L-leucine derivative that is the amide obtained by formal condensation of the carboxy group of (2S,3S)-3-(ethoxycarbonyl)oxirane-2-carboxylic acid with the amino group of N-(3-methylb
tyl)-L-leucinamide. | [Biological Activity]
Cell-permeable, ethyl ester of E-64-c. The ester is hydrolyzed by intracellular esterases to produce E-64-c. Inhibits calpain and cathepsins B, H, and L. Inhibits degradation of autophagic cargo inside autophagolysosomes. | [Biochem/physiol Actions]
E-64d is an epoxysuccinyl peptide and an inhibitor of cysteine protease cathepsin B, calpains 1 and 2. E-64d by its cathepsin B protease inhibition functionality, may serve as a potential drug for treating traumatic brain injury (TBI) and Alzheimer′s disease (AD). It inhibits gametocyte surface antigen resulting in a decreased oocyst production in Plasmodium falciparum. | [Safety Profile]
Moderately toxic by intraperitoneal route. An experimental teratogen. Experimental reproductive effects. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx. | [storage]
Store at -20°C | [References]
1) McGowan?et al.?(1989),?Inhibition of calpain in intact platelets by the thiol protease inhibitor E-64d; Biochem. Biophys. Res. Commun.,?158?432
2) Wilcox and Mason (1992),?Inhibition of cysteine proteinases in lysosomes and whole cells; Biochem. J.,?285?495
3) Mizushima?et al.?(2010), Methods in mammalian autophagy research; Cell,?140?313 |
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