E-64
| Code | Size | Price |
|---|
| AG-CP3-7006-M005 | 5 mg | £55.00 |
Quantity:
| AG-CP3-7006-M025 | 25 mg | £190.00 |
Quantity:
| AG-CP3-7006-M100 | 100 mg | £640.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
AMBIENT
Storage:
Short Term Storage: +4?C. Long Term Storage: -20?C
Documents
Further Information
Alternate Names/Synonyms:
L-trans-Epoxysuccinyl-leucylamide-(4-guanido)-butane; N-[N-(L-3-trans-Carboxyoxirane-2-carbonyl]-L-leucyl)-agmatine
Appearance:
White solid.
CAS:
66701-25-5
EClass:
32160000
Form (Short):
solid
Handling Advice:
Protect from light and moisture.
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
InChiKey:
LTLYEAJONXGNFG-HBNTYKKESA-N
Long Description:
Chemical. CAS: 66701-25-5. Formula: C15H27N5O5. Molecular Weight: 357.4. The epoxysuccinyl peptide E-64 is an irreversible, potent, and highly selective cysteine protease inhibitor. It inhibits a variety of cysteine proteases, including cathepsins K, L, S, B and H. It inhibits also papain, calpain, ficin and bromelain. Acts by forming a thioether bond with the thiol of the active cysteine. Does not inhibit serine proteases (except reversible inhibition of trypsin) like other cysteine protease inhibitors, e.g. leupeptin and antipain. E-64 is a very useful cysteine protease inhibitor for use for in vitro and in vivo studies because it shows specific inhibition, it is permeable in cells and tissues and has low toxicity. Shown to have diverse biological activities, such as antiviral (FDMV, ASFV), antiparasitic, anticancer and immunomodulatory properties. Shown to reduce bone resorption in embryonic mouse bone explants. Reduces HSC-3 tongue cancer cell invasion and induces oxidative stress and apoptosis in filarial parasites. Inhibits autophagy-associated lysosomal degradation in vitro. 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.
MDL:
MFCD00080261
Molecular Formula:
C15H27N5O5
Molecular Weight:
357.4
Package Type:
Vial
Product Description:
The epoxysuccinyl peptide E-64 is an irreversible, potent, and highly selective cysteine protease inhibitor. It inhibits a variety of cysteine proteases, including cathepsins K, L, S, B and H. It inhibits also papain, calpain, ficin and bromelain. Acts by forming a thioether bond with the thiol of the active cysteine. Does not inhibit serine proteases (except reversible inhibition of trypsin) like other cysteine protease inhibitors, e.g. leupeptin and antipain. E-64 is a very useful cysteine protease inhibitor for use for in vitro and in vivo studies because it shows specific inhibition, it is permeable in cells and tissues and has low toxicity. Shown to have diverse biological activities, such as antiviral (FDMV, ASFV), antiparasitic, anticancer and immunomodulatory properties. Shown to reduce bone resorption in embryonic mouse bone explants. Reduces HSC-3 tongue cancer cell invasion and induces oxidative stress and apoptosis in filarial parasites. Inhibits autophagy-associated lysosomal degradation in vitro. 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.
Purity:
>98% (HPLC)
SMILES:
O=C(O)[C@H]1[C@H](C(N[C@@H](CC(C)C)C(NCCCCNC(N)=N)=O)=O)O1
Solubility Chemicals:
Soluble in DMSO (20mg/ml) or water (10mg/ml). Soluble in a 1:1 mixture water/ethanol (15mg/ml).
Source / Host:
Synthetic. Originally isolated from Aspergillus japonicus.
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20?C.
References
Isolation and characterization of E-64, a new thiol protease inhibitor: K. Hanada, et al.; Agric. Biol. Chem. 42, 523 (1978) | Structure and Synthesis of E-64, a New Thiol Protease Inhibitor: K. Hanada, et al.; Agric. Biol. Chem. 42, 529 (1978) | L-trans-Epoxysuccinyl-leucylamido(4-guanidino)butane (E-64) and its analogues as inhibitors of cysteine proteinases including cathepsins B, H and L: A.J. Barrett, et al.; Biochem. J. 201, 189 (1982) | Inhibitions of cathepsin B and cathepsin L by E-64 in vivo. II. Incorporation of [3H]E-64 into rat liver lysosomes in vivo: S. Hashida, et al.; J. Biochem. 91, 1373 (1982) | In vivo and in vitro evidence for the involvement of cysteine proteinases in bone resorption: J.-M. Delaisse, et al.; BBRC 125, 441 (1984) | Thiol protease-specific inhibitor E-64 arrests human epidermoid carcinoma A431 cells at mitotic metaphase: Y. Shoji-Kasai, et al.; PNAS 85, 146 (1988) | Antiviral effects of a thiol protease inhibitor on foot-and-mouth disease virus: L.G. Kleina & M.J. Grubman; J. Virol. 66, 7168 (1992) | Inhibition of activation-induced programmed cell death and restoration of defective immune responses of HIV+ donors by cysteine protease inhibitors: A. Sarin, et al.; J. Immunol. 153, 862 (1994) | Calpain inhibition: an overview of its therapeutic potential: K.K.W. Wang & P.-W. Yuen; Trends Pharmacol. Sci. 15, 412 (1994) | Promotion of heat-induced apoptosis in FM3A cells by protease inhibitors: W.G. Zhu, et al.; BBRC 225, 924 (1996) | Demonstration that 1-trans-epoxysuccinyl-L-leucylamido-(4-guanidino) butane (E-64) is one of the most effective low Mr inhibitors of trypsin-catalysed hydrolysis. Characterization by kinetic analysis and by energy minimization and molecular dynamics simulation of the E-64-beta-trypsin complex: S.K. Sreedharan, et al.; Biochem. J. 316, 777 (1996) | Inhibition of carcinoma cell invasion and liver metastases formation by the cysteine proteinase inhibitor E-64: R. Navab, et al.; Clin. Exp. Metastasis. 15, 121 (1997) | Purification of active cysteine proteases by affinity chromatography with attached E-64 inhibitor: E. Govrin & A. Levine; Protein Expr. Purif. 15, 247 (1999) | Antiparasitic activity of cystine protease inhibitor E-64 against Giardia lamblia excystation in vitro and in vivo: E.M. Hussein, et al.; J. Egypt. Soc. Parasitol. 39, 111 (2009) | Inhibition of cathepsin B by E-64 induces oxidative stress and apoptosis in filarial parasite: M. Wadhawan, et al.; PLos One 9, e93161 (2014) | Small molecule inhibitor E-64 exhibiting the activity against African swine fever virus pS273R: B. Liu, et al.; Bioorg. Med. Chem. 35, 116055 (2021)