All Photos(1)

E0514

Sigma-Aldrich

E-64c

Calpain Inhibitor

Synonym(s):
(2S,3S)-trans-Epoxysuccinyl-L-leucylamido-3-methylbutane
Empirical Formula (Hill Notation):
C15H26N2O5
CAS Number:
Molecular Weight:
314.38
MDL number:
PubChem Substance ID:

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

powder

solubility

ethanol: 20 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

CC(C)CCNC(=O)[C@H](CC(C)C)NC(=O)[C@H]1O[C@@H]1C(O)=O

InChI

1S/C15H26N2O5/c1-8(2)5-6-16-13(18)10(7-9(3)4)17-14(19)11-12(22-11)15(20)21/h8-12H,5-7H2,1-4H3,(H,16,18)(H,17,19)(H,20,21)/t10-,11-,12-/m0/s1

InChI key

SCMSYZJDIQPSDI-SRVKXCTJSA-N

Gene Information

human ... CAPN1(823)

Biochem/physiol Actions

Cysteine protease inhibitor; membrane-impermeable calpain inhibitor. Significantly reduces calpain-mediated depletion of microtubule-associated protein (MAP2) in an animal model of an ischemic brain.

Linkage

Synthetic analog of E-64

Certificate of Analysis

Certificate of Origin

A J Barrett et al.
The Biochemical journal, 201(1), 189-198 (1982-01-01)
1. L-trans-Epoxysuccinyl-leucylamido(4-guanidino)butane (E-64) at a concentration of 0.5 mM had no effect on the serine proteinases plasma kallikrein and leucocyte elastase or the metalloproteinases thermolysin and clostridial collagenase. In contrast, 10 muM-E-64 rapidly inactivated the cysteine proteinases cathepsins B, H
B C Sondergaard et al.
Osteoarthritis and cartilage, 14(8), 738-748 (2006-03-28)
Both matrix metalloprotease (MMP) activity and cathepsin K (CK) activity have been implicated in cartilage turnover. We investigated the relative contribution of MMP activity and CK activity in cartilage degradation using ex vivo and in vivo models. Bovine articular cartilage
Eva Lindskog et al.
Applied microbiology and biotechnology, 71(4), 444-449 (2005-11-12)
Gelatin zymography revealed the presence of proteolytic activity in conditioned medium (CM) from a serum-free, non-infected Spodoptera frugiperda, Sf9 insect cell culture. Two peptidase bands at about 49 and 39 kDa were detected and found to be proform and active
T Moldoveanu et al.
Journal of molecular biology, 343(5), 1313-1326 (2004-10-20)
The endogenous calpain inhibitor, calpastatin, modulates some patho-physiological aspects of calpain signaling. Excess calpain can escape this inhibition and as well, many calpain isoforms and autolytically generated protease core fragments are not inhibited by calpastatin. There is a need, therefore
Jacques Marquay Markiewicz et al.
PLoS neglected tropical diseases, 5(4), e1002-e1002 (2011-04-13)
Exposure of Entamoeba histolytica to specific ligands induces cell polarization via the activation of signalling pathways and cytoskeletal elements. The process leads to formation of a protruding pseudopod at the front of the cell and a retracting uropod at the

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