calpeptin

Names

[ Name ]:
calpeptin

[Synonym ]:
Z-LEU-NLE-CHO
BENZYLOXYCARBONYLLEUCYL-NORLEUCINAL
N-Benzyloxycarbonyl-L-leucylnorieucinal Z-Leu-Nle-CHO
MFCD00155623
N-CBZ-L-LEUCYL-NORLEUCINAL
N-[(benzyloxy)carbonyl]-N-[(2S)-1-oxohexan-2-yl]-L-leucinamide
Z-Leu-Nle-H
CalpeptinN-Benzyloxycarbonyl-L-leucyl-norleucinal
CALPEPTIN
Z-LEU-NLE-OH
Z-LEU-NORLEUCINAL
Carbamic acid, N-[(1S)-1-[[[(1S)-1-formylpentyl]amino]carbonyl]-3-methylbutyl]-, phenylmethyl ester
N-BENZYLOXYCARBONYL-L-LEUCYLNORLEUCINAL
BENZYLOXYCARBONYLDIPEPTIDYL ALDEHYDE
N-benzyloxycarbonyl-L-leucyl-L-norleucinal
N-[(Benzyloxy)carbonyl]-N-[(2S)-1-oxo-2-hexanyl]-L-leucinamide

Biological Activity

[Description]:

Calpeptin is a potent, cell penetrating calpain inhibitor, with an ID50 of 40 nM for Calpain I in human platelets[1]. Calpeptin is also an inhibitor of cathepsin K[2].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Metabolic Enzyme/Protease >> Proteasome

Signaling Pathways >> Metabolic Enzyme/Protease >> Cathepsin

[Target]

ID50: 40 nM (Calpain I in human platelets)[1]. Cthepsin K[2]

[In Vitro]

Calpeptin (0-100 nM, 24 hours) treatment suppresses the proliferation of both WI38 VA13 and IMR90 cells in a dose-dependent manner. Calpeptin (1000 pg/ml, 24 hours) inhibits IL-6-induced cell proliferation of lung fibroblasts[3]. Cell Proliferation Assay[3] Cell Line: WI38 VA13 and IMR90 cells Concentration: 0-100 nM Incubation Time: 24 hours Result: Suppressed the proliferation in a dose-dependent manner.

[In Vivo]

Calpeptin with Bleo (0.04 mg/mouse, i.p., 3 times weekly, 28 days) administration significantly inhibits the collagen deposition and increases of calpain activity in the bleomycintreatedmouse lung tissues[3]. Animal Model: C57BL/6 female mice (Eight-week-old)[3]. Dosage: 0.04 mg/mouse. Administration: Intraperitoneally three times weekly for 28 days (together with Bleo). Result: Inhibited the collagen deposition and increase of calpain activity in the bleomycintreatedmouse lung tissues.

[References]

[1]. Tsujinaka T, et al. Synthesis of a new cell penetrating calpain inhibitor (calpeptin). Biochem Biophys Res Commun. 1988 Jun 30;153(3):1201-8.

[2]. Catalano JG, et al. Design of small molecule ketoamide-based inhibitors of cathepsin K. Bioorg Med Chem Lett. 2004 Feb 9;14(3):719-22.

[3]. Tabata C, et al. The calpain inhibitor calpeptin prevents pulmonary fibrosis in mice. Clin Exp Immunol. 2010 Dec;162(3):560-7.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
550.7±45.0 °C at 760 mmHg

[ Melting Point ]:
60-75 °C

[ Molecular Formula ]:
C₂₀H₃₀N₂O₄

[ Molecular Weight ]:
362.463

[ Flash Point ]:
286.8±28.7 °C

[ Exact Mass ]:
362.220551

[ PSA ]:
84.50000

[ LogP ]:
4.37

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.508

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Calpain mediates processing of the translation termination factor eRF3 into the IAP-binding isoform p-eRF3.

FEBS Lett. 589 , 2241-7, (2015)

The involvement of polypeptide chain-releasing factor eRF3 in translation termination and mRNA decay is well established. Moreover, the finding that the proteolytically processed isoform of eRF3 (p-eR...

Cytosolic HMGB1 controls the cellular autophagy/apoptosis checkpoint during inflammation.

J. Clin. Invest. 125(3) , 1098-110, (2015)

The intracellular protein HMGB1 is released from cells and acts as a damage-associated molecular pattern molecule during many diseases, including inflammatory bowel disease (IBD); however, the intrace...

Salbutamol inhibits RhoA activation in normal but not in desensitized bronchial smooth muscle cells.

J. Pharm. Pharmacol. 67 , 1416-20, (2015)

This study was aimed at investigating whether the β2 -adrenoceptor agonist, salbutamol, could modulate RhoA activation in normal and homologously desensitized bronchial smooth muscle cells (BSMC).Seru...