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117591-20-5

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  • Carbamic acid, [(1S)-1-[[[(1S)-1-formylpentyl]amino]carbonyl]-3-methylbutyl]-, phenylmethyl ester

    Cas No: 117591-20-5

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117591-20-5 Usage

Chemical Properties

white to off-white powder

Uses

Calpeptin is used to to inhibit the activities of cathepsin L and calpain-1. Calpeptin blocked the expression of aspartyl protease cathepsin D, amyloid precursor protein, and calparin. It acts as an inhibitor of the Ca2+-dependent protease, calpain. Prevents collagen- and thrombin-induced platelet aggregation, probably by blocking calpain induced phospholipase C and thromboxane synthase activation. Potent cathepsin L inhibitor. It is shown to preferentially inhibit a subset of protein-tyrosine phosphatases.

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).

Biological Activity

Potent, cell-permeable inhibitor of the Ca 2+ -dependent protease, calpain. Prevents collagen- and thrombin-induced platelet aggregation, probably by blocking calpain induced phospholipase C and thromboxane synthase activation. Potent cathepsin L inhibitor. Recently shown to preferentially inhibit a subset of protein-tyrosine phosphatases.

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.

in vitro

calpeptin reduced production of tgf-b1, il-6, angiopoietin-1 and collagen synthesis from lung fibroblasts. calpeptin also reduced both angiopoietin-1-dependent migration and il-6-dependent proliferation of the cells, which could be the underlying mechanism of the preventive effect of calpeptin on pulmonary fibrosis [1].

in vivo

the preventive effect of calpeptin has been examined on bleomycin-induced pulmonary fibrosis in mice. histological examinations and quantitative measurements of related proteins in bleomycin-treated mouse lung tissues with or without calpeptin were performed. calpeptin histologically ameliorated bleomycininduced pulmonary fibrosis in mice. results showed that calpeptin decreased the expression of il-6, tgf-b1, angiopoietin-1 and collagen type ia1 mrna in mouse lung tissues [1].

IC 50

5 nm for human calpain 1

references

[1] tabata c,tabata r,nakano t. the calpain inhibitor calpeptin prevents bleomycin-induced pulmonary fibrosis in mice. clin exp immunol.2010 dec;162(3):560-7.

Check Digit Verification of cas no

The CAS Registry Mumber 117591-20-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,7,5,9 and 1 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 117591-20:
(8*1)+(7*1)+(6*7)+(5*5)+(4*9)+(3*1)+(2*2)+(1*0)=125
125 % 10 = 5
So 117591-20-5 is a valid CAS Registry Number.
InChI:InChI=1/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

117591-20-5 Well-known Company Product Price

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  • Sigma

  • (C8999)  Calpeptin  ≥98% (HPLC)

  • 117591-20-5

  • C8999-5MG

  • 921.96CNY

  • Detail
  • Sigma

  • (C8999)  Calpeptin  ≥98% (HPLC)

  • 117591-20-5

  • C8999-25MG

  • 3,728.79CNY

  • Detail

117591-20-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name Calpeptin,N-Benzyloxycarbonyl-L-leucylnorleucinal

1.2 Other means of identification

Product number -
Other names Z-LEU-NLE-CHO

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:117591-20-5 SDS

117591-20-5Relevant articles and documents

Cycloalkylcarbonylamino Acid Derivative and Process For Producing The Same

-

Page/Page column 68, (2009/05/28)

Cycloalkylcarbonylamino acid derivatives, which are raw material intermediates of a novel cycloalkane carboxamide derivative that selectively inhibits cathepsin K, and a production process thereof, are provided. A cycloalkylcarbonylamino acid derivative r

OXAZOLONE DERIVATIVE

-

Page/Page column 92-93, (2008/12/07)

Novel raw material compounds are provided that are useful for producing novel cycloalkane carboxamide derivatives having cathepsin K inhibitory action. An oxazolone derivative represented by formula (I): [wherein, R1 represents a substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted phenyl group, substituted or unsubstituted naphthyl group or substituted or unsubstituted heterocyclic group, and ring A represents a saturated cyclic alkylidene group having 6 to 7 carbon atoms].

Ketoheterocycle-based inhibitors of cathepsin K: A novel entry into the synthesis of peptidic ketoheterocycles

Tavares, Francis X.,Deaton, David N.,Miller, Aaron B.,Miller, Larry R.,Wright, Lois L.

, p. 3891 - 3895 (2007/10/03)

Ketoheterocyclic inhibitors of cathepsin K have been disclosed. SAR of potency enhancing P2-P3 groups coupled with ketoheterocyclic warheads to provide cathepsin K inhibitors have been described. In addition, a novel route to access

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