oxiranecarboxylicacid,3-(((1-(((4-((aminoiminomethyl)amino)butyl)amino)carbon - Names and Identifiers
Name | N-(trans-epoxysuccinyl)-L-leucine 4-guanidinobutylamide
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Synonyms | E64 E-64 proteinaseinhibitore64 thiolproteaseinhibitor E-64 Protease Inhibitor trans-epoxysuccinyl-L-leucylamido-*(4-guanidino)B L-TRANS-3-CARBOXYOXIRAN-2-CARBONYL-L-LEUCYLAGMATINE TRANS-EPOXYSUCCINYL-L-LEUCYLAMIDO-*(4-GU ANIDINO)BUT N-(trans-epoxysuccinyl)-L-leucine 4-guanidinobutylamide (2S, 3S)-TRANS-EPOXY SUCCINYL-L-LEUCYLAMIDO-(4-GUANIDINO) BUTANE oxiranecarboxylicacid,3-(((1-(((4-((aminoiminomethyl)amino)butyl)amino)carbon (2S,3S)-3-(((S)-1-((4-Guanidinobutyl)amino)-4-methyl-1-oxopentan-2-yl)carbamoyl)oxirane-2-carb (2S,3S)-3-(((S)-1-((4-Guanidinobutyl)amino)-4-methyl-1-oxopentan-2-yl)carbamoyl)oxirane-2-carboxylic acid (2R,3R)-3-{[(2S)-1-({4-[(diaminomethylidene)amino]butyl}amino)-4-methyl-1-oxopentan-2-yl]carbamoyl}oxirane-2-carboxylic acid (2S,3S)-3-{[(2S)-1-({4-[(diaminomethylidene)amino]butyl}amino)-4-methyl-1-oxopentan-2-yl]carbamoyl}oxirane-2-carboxylic acid
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CAS | 66701-25-5
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EINECS | 613-978-4 |
InChI | InChI=1/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 |
InChIKey | LTLYEAJONXGNFG-DCAQKATOSA-N |
oxiranecarboxylicacid,3-(((1-(((4-((aminoiminomethyl)amino)butyl)amino)carbon - Physico-chemical Properties
Molecular Formula | C15H27N5O5
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Molar Mass | 357.41 |
Density | 1.44±0.1 g/cm3(Predicted) |
Melting Point | >170°C (dec.) |
Water Solubility | Soluble in DMSO (25mg/ml), or water (20mg/ml) |
Solubility | Soluble in DMSO and water. |
Appearance | White powder. |
Color | White or off-white |
BRN | 1405664 |
pKa | 3.16±0.40(Predicted) |
Storage Condition | 2-8°C |
Stability | Stable for 1 year from date of purchase as supplied. Solutions in 1 |
Sensitive | Light Sensitive |
Refractive Index | 1.617 |
MDL | MFCD00080261 |
Use | This product is for scientific research only and shall not be used for other purposes. |
In vitro study | E-64 rapidly inhibited the cysteine proteases cathepsin B,H ,L, and papain, whereas it had no effect on serine proteases or metalloproteases. E-64, a specific inhibitor of cysteine proteases, effectively blocks ovarian cancer cell invasion in vitro. In addition, E-64 also exhibited in vitro antiparasitic activity against Giardia lamella decapsulation. E-64 improves the pre-implantation development of somatic cell nuclear transfer embryos, which shows another important effect of E-64. |
In vivo study | E-64 caused a significant reduction in the number of spontaneous metastases in M5076 tumor mice and had no effect on the formation of experimental metastases. E-64 also showed antiparasitic activity against mice infected with Giardia lamellae. |
oxiranecarboxylicacid,3-(((1-(((4-((aminoiminomethyl)amino)butyl)amino)carbon - Risk and Safety
Safety Description | S22 - Do not breathe dust.
S24/25 - Avoid contact with skin and eyes.
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WGK Germany | 3 |
RTECS | RR0390000 |
FLUKA BRAND F CODES | 10 |
HS Code | 29252900 |
oxiranecarboxylicacid,3-(((1-(((4-((aminoiminomethyl)amino)butyl)amino)carbon - Introduction
E-64 is an irreversible, powerful, highly selective cysteine protease inhibitor. E-64 does not react with non-protease functional sulfur groups, such as L-lactate dehydrogenase or creatine kinase. E-64 like other cysteine protease inhibitors, such as leucopeptide and antipain, do not inhibit serine proteases (except trypsin). E-64 trans-epoxysuccinyl (active moiety) irreversibly binds to many active sulfhydryl groups of cysteine proteases, such as papain, kiwifruit enzyme (actinidase), cathepsin B,H, and L. E-64 is a very useful cysteine protease inhibitor for in vivo research, because it has specific inhibitory characteristics, it can penetrate into cells and tissues, and has low toxicity.
Last Update:2022-10-16 17:27:48
oxiranecarboxylicacid,3-(((1-(((4-((aminoiminomethyl)amino)butyl)amino)carbon - Reference Information
biological activity | E-64 is a non-reversible, selective cysteine protease inhibitor, also inhibit papain, calpain and cathepsin B, H, but does not inhibit serine or aspartic proteases. The IC50 for inhibition of papain was 9nm. E-64 can induce oxidative stress and apoptosis in filarial parasites. |
Target | Value |
Cysteine protease
(Cell-free assay)
| 9 nM |
Use | 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 retention of specificity |
Last Update:2024-04-09 21:04:16