CAS Number66701-25-5
SynonymsE64; (L-3-trans-carboxyoxiran-2-carbonyl)-L-leucyl-agmatin; L-TRANS-EPOXYSUCCINYL-LEU-4-GUANIDINOBUTYLAMIDE; E-64; E-64 HEMIHYDRATE; E-64,L-trans-Epoxysuccinyl-Leu-agMatine; L-TRANS-EPOXYSUCCINYL-LEU-AGMATINE; EPOXYSUCCINYL-L-LEUCYLAMIDO-(4-GUANIDINO)BUTANE; MFCD07366493
Molecular FormulaC15H27N5O5
Molecular Weight357.41
Purity98.00%
Density1.4±0.1 g/cm3
Melting Point182ºC
Appearancewhite solid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 66701-25-5 |
| Catalog No. | 2A-9046466 |
| Chinese Name | N-(反式-环氧丁二酰基)-L-亮氨酸-4-胍基丁基酰胺 |
| Synonyms | E64; (L-3-trans-carboxyoxiran-2-carbonyl)-L-leucyl-agmatin; L-TRANS-EPOXYSUCCINYL-LEU-4-GUANIDINOBUTYLAMIDE; E-64; E-64 HEMIHYDRATE; E-64,L-trans-Epoxysuccinyl-Leu-agMatine; L-TRANS-EPOXYSUCCINYL-LEU-AGMATINE; EPOXYSUCCINYL-L-LEUCYLAMIDO-(4-GUANIDINO)BUTANE; MFCD07366493 |
| Molecular Formula | C15H27N5O5 |
| Molecular Weight | 357.41 |
| Purity | 98.00 |
| Density | 1.4±0.1 g/cm3 |
| Melting Point | 182ºC |
| Appearance | white solid |
| Water Solubility | H2O: 20 mg/mL, clear, colorless |
| Storage Condition | Store in a sealed container filled with inert gas |
| Application | E-64 is a potent irreversible inhibitor of cysteine proteases with an IC50 of 9 nM for papin. |
| PubChem ID | 329798998 |
| SMILES | CC(C)CC(NC(=O)C1OC1C(=O)O)C(=O)NCCCCN=C(N)N |
| InChI | InChI=1S/C15H27N5O5/c1-8(2)7-9(20-13(22)10-11(25-10)14(23)24)12(21)18-5-3-4-6-19-15(16)17/h8-11H,3-7H2,1-2H3,(H,18,21)(H,20,22)(H,23,24)(H4,16,17,19)/t9-,10+,11+/m0/s1 |
| InChI Key | LTLYEAJONXGNFG-UHFFFAOYSA-N |
| Hazard Symbols | transportation |
| Bioactivity | E-64 is a potent irreversible inhibitor against general cysteine proteases with IC50 of 9 nM for papain. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Metabolic Enzyme/Protease >> Cathepsin Research Areas >> Inflammation/Immunology Target IC50: 9 nM (Papain)[1] In Vitro E-64 is a cathepsin B-specific inhibitor, and its binding modes with papain, actinidin, cathepsin L, and cathepsin K have been reviewed at the atomic level. E-64 has been widely used as a potent and irreversible (covalent-type) inhibitor for many cysteine proteases such as papain, ficin, actinidin, cathepsin B and L[1]. The S.cervi adult parasites are incubated in the Kreb's Ringer bicarbonate (KRB) maintenance medium for 8 h at 37°C, 5% CO2 with 5, 10, 20 and 40 μM concentration of E-64. E-64 shows a concentration and time dependent decrease in motility and viability of the parasites (EC50=16 μM)[2]. In Vivo A broad spectrum of expression of CD4 and CD19 is found exists in both the islets and pancreatic lymph nodes (PLNs) and that anti-serpin B13 mAb exposure causes a significant shift that favored cells expressing low-to-intermediate amounts of these markers. However, this shift is abolished in animals that receive anti-serpin B13 mAb in the presence of the protease inhibitor E-64 (E64), which maintains its blocking activity under the experimental conditions used[3]. Dahl salt-sensitive (SS) rats are fed an 8% high salt NaCl diet and intravenously infused with the irreversible cysteine cathepsin inhibitor E-64 (1 mg/day) or the vehicle (control). Both the control and E-64 infused groups develope significant hypertension and kidney damage, and no difference of the mean arterial pressure and the hypertension-associated albuminuria is observed between the groups[4]. Kinase Assay The Cathepsin B activity is determined using Z-Arg-Arg-4mβNA as substrate with slight modifications. The crude extract is pre-incubated at 37°C for 5 min in 50 mM sodium acetate buffer, pH 5.0 containing 1 mM EDTA and 5 mM DTT. The substrate (final concentration, 100 μM) is added to make the final assay volume of 1 mL. The reaction mixture is incubated at 37°C for 30 min. The reaction is terminated by adding equal volume of stopping reagent containing Fast Garnet GBC salt (1 mg/mL), 10 mM pHMB and 50 mM EDTA, pH 6.0. The extraction of product, β-napthylamine (β-NA), is carried out with n-butanol. After complete layer separation, the absorbance is measured in n-butanol layer and activity is calculated using molar extinction coefficient of β-napthylamine solution as 31.5 M/cm per sec at 520 nm. One unit of enzyme activity is defined as the amount of enzyme liberating 1 μmol of βNA per minute at 37°C. The half maximal inhibitory concentration (IC50) is calculated by plotting the graph between the different concentration of E-64 and the % inhibition in cathepsin B activity. Here, IC50 indicates the concentration of the E-64 required to inhibit the parasitic cathepsin B activity by half[2]. Animal Admin Mice[3] The NOD/LtJ and BDC2.5 T cell receptor (TCR) transgenic NOD mice are used to study the effects of treatment with anti-serpin B13 monoclonal antibody (mAb). Four-week-old female NOD/LtJ mice are injected intravenously four times over a period of 10 days with anti-serpin B13 mAb (100 μg/injection). In addition, during the same period, some animals are also injected intraperitoneally with the protease inhibitor E64 at 10 mg/kg/day for several days. Control mice are treated with diluent (a sterilized PBS solution containing 10% DMSO) and control IgG. The solutions containing E64 or DMSO are prepared immediately before use. Twenty-four hours after the last injection, the mice are killed, and cells from their lymphoid organs and pancreatic islets are subjected to FACS analysis. Rats[4] Seven-week old male Dahl Salt Sensitive rats (SS/JrHsdMcwi) are used. Briefly, 8-week old anesthetized SS rats have their left femoral artery and vein catheterized. Both catheters are fixed and exteriorized from the back of the neck and the arterial line is connected to a heparinized saline infusion pump that is in line with a blood pressure transducer, and the venous line is connected to a saline infusion pump. Animals are allowed 360° movement using a tether-swivel system. This preparation allowed chronic venous infusion and arterial blood pressure measurement in conscious, freely moving rats. A stable baseline blood pressure is obtained for 4 days prior to switching both groups to an 8.0% NaCl diet and the simultaneous addition of E-64 (1 mg/day; 280 mM stock in DMSO) or the vehicle (DMSO in saline) control to the venous catheter. Daily MAP is calculated by averaging MAP taken every min over the beginning 3 h period of the rat sleep cycle. References [1]. Matsumoto K, et al. Structural basis of inhibition of cysteine proteases by E-64 and its derivatives. Biopolymers. 1999;51(1):99-107. [2]. Wadhawan M, et al. Inhibition of cathepsin B by E-64 induces oxidative stress and apoptosis in filarial parasite. PLoS One. 2014 Mar 25;9(3):e93161. [3]. Baldzizhar R, et al. Anti-serpin antibody-mediated regulation of proteases in autoimmune diabetes. J Biol Chem. 2013 Jan 18;288(3):1612-9. [4]. Blass G, et al. Chronic cathepsin inhibition by E-64 in Dahl salt-sensitive rats. Physiol Rep. 2016 Sep;4(17). pii: e12950. Chemical & Physical Properties Density 1.4±0.1 g/cm3 Melting Point 182ºC Molecular Formula C15H27N5O5 Molecular Weight 357.405 Exact Mass 357.201233 PSA 169.93000 LogP -1.46 Index of Refraction 1.618 InChIKey LTLYEAJONXGNFG-UHFFFAOYSA-N SMILES CC(C)CC(NC(=O)C1OC1C(=O)O)C(=O)NCCCCN=C(N)N Storage condition 2-8°C Water Solubility H2O: 20 mg/mL, clear, colorless |
| Use of | E-64 is a potent irreversible inhibitor against general cysteine proteases with IC50 of 9 nM for papain. Properties Articles115 Synonym More Synonyms E-64 Biological Activity Description E-64 is a potent irreversible inhibitor against general cysteine proteases with IC50 of 9 nM for papain. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Metabolic Enzyme/Protease >> Cathepsin Research Areas >> Inflammation/Immunology IC50: 9 nM (Papain)[1] References [1]. Matsumoto K, et al. Structural basis of inhibition of cysteine proteases by E-64 and its derivatives. Biopolymers. 1999;51(1):99-107. [2]. Wadhawan M, et al. Inhibition of cathepsin B by E-64 induces oxidative stress and apoptosis in filarial parasite. PLoS One. 2014 Mar 25;9(3):e93161. [3]. Baldzizhar R, et al. Anti-serpin antibody-mediated regulation of proteases in autoimmune diabetes. J Biol Chem. 2013 Jan 18;288(3):1612-9. [4]. Blass G, et al. Chronic cathepsin inhibition by E-64 in Dahl salt-sensitive rats. Physiol Rep. 2016 Sep;4(17). pii: e12950. Chemical & Physical Properties Molecular Formula C15H27N5O5 Exact Mass 357.201233 PSA 169.93000 LogP -1.46 Index of Refraction 1.618 InChIKey LTLYEAJONXGNFG-UHFFFAOYSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available See reverse side of invoice or packing slip. |
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