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Merck
CN

C8999

Calpeptin

≥98% (HPLC), calpain inhibitor, powder

Synonym(s):

N-Benzyloxycarbonyl-L-leucylnorieucinal, Z-Leu-Nle-CHO

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About This Item

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

Key Documents

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Product Name

Calpeptin, ≥98% (HPLC)

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

Related Categories

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 calpain inhibitor and rho kinase activator.
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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000502860
0000502859
0000502859
0000502860
0000404045

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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)
Heike Hardelauf et al.
Lab on a chip, 11(16), 2763-2771 (2011-06-29)
Spatially defined neuronal networks have great potential to be used in a wide spectrum of neurobiology assays. We present an original technique for the precise and reproducible formation of neuronal networks. A PDMS membrane comprising through-holes aligned with interconnecting microchannels
Grace Soong et al.
The Journal of infectious diseases, 205(10), 1571-1579 (2012-03-30)
The USA300 strains of Staphylococcus aureus are the major cause of skin and soft tissue infection in the United States. Invasive USA300 infection has been attributed to several virulence factors, including protein A and the α-hemolysin (Hla), which cause pathology
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)
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