M8699

Sigma-Aldrich

(R)-MG132

Synonym(s):
Z-L-Leu-D-Leu-L-Leu-al
Empirical Formula (Hill Notation):
C26H41N3O5
CAS Number:
Molecular Weight:
475.62

Quality Level

assay

≥98%

form

crystalline solid or supercooled liquid

solubility

DMSO or DMF: 25 mg/mL

storage temp.

−20°C

SMILES string

CC(C)C[C@@H](C(N[C@H](C(N[C@H](C=O)CC(C)C)=O)CC(C)C)=O)NC(OCC1=CC=CC=C1)=O

Application

(R)-MG132 has been used in ubiquitination assay and is used as a proteasome inhibitor.

Biochem/physiol Actions

MG132 (carbobenzoxy-Leu-Leu-leucinal) is a tri-peptide aldehyde. It possesses antitumor activity and boosts cytostatic/cytotoxic effects of chemo- and radiotherapy. (R)-MG132 is a potent, membrane-permeable proteasome inhibitor. It can inhibit proteasome activity in lysates of J558L multiple myeloma cells and EMT6 breast cancer cells. The (R)-MG132 stereoisomer is a more effective inhibitor of chymotrypsin-like (ChTL), trypsin-like (TL), and peptidylglutamyl peptide hydrolyzing proteasome (PGPH) activities than the (S)-MG132.

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Alternative promotion and suppression of metastasis by JNK2 governed by its phosphorylation.
Hu S, et al.
Oncotarget, 8(34), 56569-56569 (2017)
Studies of the synthesis of all stereoisomers of MG-132 proteasome inhibitors in the tumor targeting approach.
Mroczkiewicz M, et al.
Journal of Medicinal Chemistry, 53(4), 1509-1518 (2010)
A Mad2-Mediated Translational Regulatory Mechanism Promoting S-Phase Cyclin Synthesis Controls Origin Firing and Survival to Replication Stress.
Gay S, et al.
Molecular Cell, 70(4), 628-638 (2018)
Fang Guo et al.
Molecular neurobiology, 54(10), 7597-7609 (2016-11-11)
Autophagy and the ubiquitin proteasome system (UPS), as two major protein degradation pathways, coordinate with each other in regulating programmed cell death. Autophagy can compensate for the UPS impairment-induced cell dysfunction and apoptosis. However, it is not clear how cells...
Michał Mroczkiewicz et al.
Journal of medicinal chemistry, 53(4), 1509-1518 (2010-02-02)
MG-132 is a tripeptide aldehyde (Z-l-leu-l-leu-l-leu-H, 2) proteasome inhibitor that exerts antitumor activity and enhances cytostatic/cytotoxic effects of chemo- and radiotherapy. Because of a troublesome synthesis of tripeptides with a non-natural configuration and modified side chains of amino acids, only...

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