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Key Documents

M8699

Sigma-Aldrich

(R)-MG132

Synonym(s):

Z-L-Leu-D-Leu-L-Leu-al

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About This Item

Empirical Formula (Hill Notation):
C26H41N3O5
CAS Number:
Molecular Weight:
475.62
UNSPSC Code:
12352200
NACRES:
NA.32

Assay

≥98%

Quality Level

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.

Physical form

crystalline solid or supercooled liquid

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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A Mad2-Mediated Translational Regulatory Mechanism Promoting S-Phase Cyclin Synthesis Controls Origin Firing and Survival to Replication Stress.
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Activation of anaphase-promoting complex by p53 induces a state of dormancy in cancer cells against chemotherapeutic stress.
Dai Y, et al.
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Determination of H-ATPase Activity in Arabidopsis Guard Cell Protoplasts through H-pumping Measurement and H-ATPase Quantification.
Yamauchi S and Ken-ichiro S
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Natural and synthetic progestogens have been commonly used to prevent recurrent pregnancy loss in women with inadequate progesterone secretion or reduced progesterone sensitivity. However, the clinical efficacy of progesterone and its analogs for maintaining pregnancy is variable. Additionally, the underlying
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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