AdipoGen Life Sciences

E-64

CHF 60.00

In stock

AG-CP3-7006-M0055 mgCHF 60.00

AG-CP3-7006-M02525 mgCHF 240.00

AG-CP3-7006-M100100 mgCHF 840.00

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Product Details
Synonyms	L-trans-Epoxysuccinyl-leucylamide-(4-guanido)-butane; N-[N-(L-3-trans-Carboxyoxirane-2-carbonyl]-L-leucyl)-agmatine
Product Type	Chemical
Properties
Formula	C₁₅H₂₇N₅O₅
MW	357.4
CAS	66701-25-5
RTECS	RR0390000
Source/Host Chemicals	Synthetic. Originally isolated from Aspergillus japonicus.
Purity Chemicals	≥98% (HPLC)
Appearance	White solid.
Solubility	Soluble in DMSO (20mg/ml) or water (10mg/ml). Soluble in a 1:1 mixture water/ethanol (15mg/ml).
InChi Key	LTLYEAJONXGNFG-HBNTYKKESA-N
Smiles	O=C(O)[C@H]1[C@H](C(N[C@@H](CC(C)C)C(NCCCCNC(N)=N)=O)=O)O1
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

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.

Product 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)

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