AdipoGen Life Sciences

Loxistatin acid [E-64c]

CHF 70.00

In stock

AG-CP3-7007-M0011 mgCHF 70.00

AG-CP3-7007-M0055 mgCHF 280.00

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Product Details
Synonyms	Ep 475; 2S,3S-trans-(Carboxyoxirane-2-carbonyl)-L-leucine-(3-methylbutyl) amide; NSC 694279
Product Type	Chemical
Properties
Formula	C₁₅H₂₆N₂O₅
MW	314.4
CAS	76684-89-4
RTECS	RR0404200
Source/Host Chemicals	Synthetic.
Purity Chemicals	≥98% (HPLC)
Appearance	White solid.
Solubility	Soluble in DMSO (10mg/ml) or ethanol (10mg/ml). Slightly soluble in water (1mg/ml).
InChi Key	SCMSYZJDIQPSDI-QJPTWQEYSA-N
Smiles	O=C(O)[C@H]1[C@H](C(N[C@@H](CC(C)C)C(NCCC(C)C)=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

E-64c is a potent cell-impermeable epoxysuccinyl peptide inhibitor of calpain and other cysteine proteases, such as papain, cathepsin B, H and L. Does not inhibit the serine proteases trypsin, chymotrypsin or elastase.
E-64c is an active metabolite of the protease inhibitor E-64d (Prod. No. AG-CR1-3737), and a synthetic analog of E-64 (Prod. No. AG-CP3-7006). Studies indicate that E-64c is a more potent inhibitor of cathepsins B and L compared to E-64.
E-64c has in vitro antiviral, antiparasitic and immunomodulatory properties. It reduces the autocatalytic activity of the foot-and-mouth-disease virus (FMDV) leader protease, reduces infection of HEK293T cells by an HIV-based virus system pseudotyped with SARS-CoV spike glycoprotein in a concentration-dependent manner, inhibits human rotavirus replication, and exhibits entry-blocking effects against MERS-CoV. It also inhibits the trypanosomal cysteine protease cruzain. Significantly reduces calpain-mediated depletion of microtubule-associated protein (MAP2) in an animal model of an ischemic brain.

Product References

The effect of an in vivo-injected thiol protease inhibitor, E-64-c, on the calcium-induced degeneration of myofilaments: S. Ishiura, et al.; J. Biochem. 90, 1557 (1981)
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)
In vitro and in vivo inhibition of cysteine proteinases by EST, a new analog of E-64: M. Tamai, et al.; J. Pharmacobiodyn. 9, 672 (1986)
Mode of binding of E-64-c, a potent thiol protease inhibitor, to papain as determined by X-ray crystal analysis of the complex: K. Matsumoto, et al.; FEBS Lett. 245, 177 (1989)
Calcium-activated neutral protease inhibitor (E-64c) and reperfusion for experimental myocardial infarction: G. Toda, et al.; Jpn. Heart J. 30, 375 (1989)
Protease inhibitors prevent the development of human rotavirus-induced diarrhea in suckling mice: T. Ebina & K. Tsukada; Microbiol. Immunol. 35, 583 (1991)
Antiviral effects of a thiol protease inhibitor on foot-and-mouth disease virus: L.G. Kleina & M.J. Grubman; J. Virol. 66, 7168 (1992)
Structural basis of inhibition of cysteine proteases by E-64 and its derivatives: K. Matsumoto, et al.; Pept. Sci. 51, 99 (1999)
Design, synthesis and evaluation of d-homophenylalanyl epoxysuccinate inhibitors of the trypanosomal cysteine protease cruzain: W.R. Roush, et al.; Tetrahedron 56, 9747 (2000)
Inhibitors of cathepsin L prevent severe acute respiratory syndrome coronavirus entry: G. Simmons, et al.; PNAS 102, 11876 (2005)
Safe, High-Throughput Screening of Natural Compounds of MERS-CoV Entry Inhibitors Using a Pseudovirus Expressing MERS-CoV Spike Protein: J.Y. Kim, et al.; Int. J. Antimicrob. Agents 52, 730 (2018)

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