ChemicalBook CAS DataBase List 88321-09-9

88321-09-9

Name	EST
CAS	88321-09-9
Molecular Formula	C17H30N2O5
MDL Number	MFCD00132883
Molecular Weight	342.43
MOL File	88321-09-9.mol

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)-

Chemical Properties

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
color	Fine needles from EtOH
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.

Safety Data

Hazard Codes	Xi
Risk Statements	36/37/38 less more
Safety Statements	26-36-24/25 less more
RIDADR	3077
WGK Germany	2
RTECS	RR0404300
HS Code	29242990
Toxicity	cyt-ham:lng 200 mg/L IYKEDH 17,815,86 less more

Hazard Information

Description

E-64d is an irreversible, membrane-permeable inhibitor of lysosomal and cytosolic cysteine proteases and has diverse biological activities. 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. E-64d (20-200 μM) induces cell cycle arrest at the G₂/M phase in A431 human epidermoid carcinoma cells. It inhibits protease-resistant prion protein accumulation in scrapie-infected neuroblastoma cells with an IC₅₀ value of 0.5 μM. 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.

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

Spectrum Detail

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