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474791

Sigma-Aldrich

Z-Leu-Leu-Leu-al

InSolution, ≥98%, 10 mM, reversible proteasome inhibitor

Synonyme(s) :

MG-132

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About This Item

Formule empirique (notation de Hill):
C26H41N3O5
Numéro CAS:
133407-82-6
Poids moléculaire :
475.62
Numéro MDL:
MFCD00674886
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

liquid

Fabricant/nom de marque

Calbiochem®

Conditions de stockage

OK to freeze
protect from light

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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

InChI

1S/C26H41N3O5/c1-17(2)12-21(15-30)27-24(31)22(13-18(3)4)28-25(32)23(14-19(5)6)29-26(33)34-16-20-10-8-7-9-11-20/h7-11,15,17-19,21-23H,12-14,16H2,1-6H3,(H,27,31)(H,28,32)(H,29,33)/t21-,22-,23-/m0/s1

Clé InChI

TZYWCYJVHRLUCT-VABKMULXSA-N

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Amino Acid Sequence

Z-Leu-Leu-Leu-al

Description générale

Potent, reversible, and cell-permeable proteasome inhibitor (Ki = 4 nM). Reduces the degradation of ubiquitin-conjugated proteins in mammalian cells and permeable stains of yeast by the 26S complex without affecting its ATPase or isopeptidase activities. Activates c-Jun N-terminal kinase (JNK1) and inhibits NF-κB activation (IC50 = 3 µM).

Actions biochimiques/physiologiques

Cell permeable: yes
Product does not compete with ATP.
Reversible: yes
Target IC50: 3 µM in inhibiting NF-κB activation
Target Ki: 4 nM as proteasome inhibitor

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Irritant (B)

Forme physique

A 10 mM (1 mg/210 µl) or (5mg/1050 µl) solution of MG-132 (Cat. No. 474790) in DMSO.

Autres remarques

Meriin, A.B., et al. 1998. J. Biol. Chem.273, 6373.
Adams, J., and Stein, R. 1996. Ann. Rep. Med. Chem.31, 279.
Lee, D.H., and Goldberg, A.L. 1996. J. Biol. Chem.271, 27280.
Wiertz, E.J.H.J., et al. 1996. Cell84, 769.
Read, M.A., et al. 1995. Immunity2, 493.
Rock, K.L., et al. 1994. Cell78, 761.

Informations légales

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

188.6 °F - closed cup - (Dimethylsulfoxide)

Point d'éclair (°C)

87 °C - closed cup - (Dimethylsulfoxide)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

D H Lee et al.
The Journal of biological chemistry, 271(44), 27280-27284 (1996-11-01)
We have studied whether various agents that inhibit purified yeast and mammalian 26 S proteasome can suppress the breakdown of different classes of proteins in Saccharomyces cerevisiae. The degradation of short-lived proteins was inhibited reversibly by peptide aldehyde inhibitors of
E J Wiertz et al.
Cell, 84(5), 769-779 (1996-03-08)
Human cytomegalovirus (HCMV) down-regulates expression of MHC class I products by selective proteolysis. A single HCMV gene, US11, which encodes an endoplasmic reticulum (ER) resident type-I transmembrane glycoprotein, is sufficient to cause this effect. In US11+cells, MHC class I molecules
A B Meriin et al.
The Journal of biological chemistry, 273(11), 6373-6379 (1998-04-16)
Inhibition of the major cytosolic protease, proteasome, has been reported to induce programmed cell death in several cell lines, while with other lines, similar inhibition blocked apoptosis triggered by a variety of harmful treatments. To elucidate the mechanism of pro-
Clarissa Braun et al.
Cell stress, 5(12), 176-182 (2021-12-18)
Programmed cell death protein 4 (PDCD4) exerts critical functions as tumor suppressor and in immune cells to regulate inflammatory processes. The phosphoinositide 3-kinase (PI3K) promotes degradation of PDCD4 via mammalian target of rapamycin complex 1 (mTORC1). However, additional pathways that
M A Read et al.
Immunity, 2(5), 493-506 (1995-05-01)
Multiple cell adhesion proteins are up-regulated in vascular endothelial cells in response to TNF alpha and other inflammatory cytokines. This increase in cell adhesion gene expression is thought to require the transcription factor NF-kappa B. Here, we show that peptide
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