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C8999

Sigma-Aldrich

Calpeptin

≥98% (HPLC)

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Synonym(s):
N-Benzyloxycarbonyl-L-leucylnorieucinal, Z-Leu-Nle-CHO
Empirical Formula (Hill Notation):
C20H30N2O4
CAS Number:
117591-20-5
Molecular Weight:
362.46
MDL number:
MFCD00155623
UNSPSC Code:
12352200
PubChem Substance ID:
329775192
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL, clear

shipped in

wet ice

storage temp.

−20°C

SMILES string

CCCC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1)C=O

InChI

1S/C20H30N2O4/c1-4-5-11-17(13-23)21-19(24)18(12-15(2)3)22-20(25)26-14-16-9-7-6-8-10-16/h6-10,13,15,17-18H,4-5,11-12,14H2,1-3H3,(H,21,24)(H,22,25)/t17-,18-/m0/s1

InChI key

PGGUOGKHUUUWAF-ROUUACIJSA-N

General description

Calpeptin (Z-Leu-nLeu-H) is a cell permeable, peptide aldehyde inhibitor. It is more sensitive to calpain I compared to other inhibitors, such as Z-Leu-Met-H and leupeptin. Calpeptin stimulates neurite elongation in differentiating pheochromocytoma (PC12) cells. Calpeptin decreases microgliosis, astrogliosis, axonal damage and neuron and oligodendrocyte death in experimental autoimmune encephalomyelitis (EAE) spinal cord. Therefore, it can be considered as a potent therapeutic for treating EAE and multiple sclerosis (MS).

Application

Calpeptin has been used as a calpain inhibitor.

Biochem/physiol Actions

Calpeptin is a rho kinase activator and an inhibitor of calpains, a family of calcium-dependent cysteine proteases involved in apoptosis, long-term potentiation in neurons, and cell cycle progression.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Grace Soong et al.
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Inhibition of histone deacetylase 3 (HDAC3) mediates ischemic preconditioning and protects cortical neurons against ischemia in rats.
Yang X, et al.
Frontiers in Molecular Neuroscience, 9, 131-131 (2016)
Hector N Aguilar et al.
PloS one, 6(6), e20903-e20903 (2011-06-23)
The 'phosphate-binding tag' (phos-tag) reagent enables separation of phospho-proteins during SDS-PAGE by impeding migration proportional to their phosphorylation stoichiometry. Western blotting can then be used to detect and quantify the bands corresponding to the phospho-states of a target protein. We
Calpeptin, a calpain inhibitor, promotes neurite elongation in differentiating PC12 cells.
Pinter M, et al.
Neuroscience Letters, 170(1), 91-93 (1994)
Calpeptin attenuated inflammation, cell death, and axonal damage in animal model of multiple sclerosis.
Guyton M K, et al.
Journal of Neuroscience Research, 88(11), 2398-2408 (2010)
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