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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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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)
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