1211877-36-9

Basic information

• Product Name: (R)-MG132
• Synonyms: (R)-MG132;Cbz-L-leu-D-leu-L-leu-H;N-[(Phenylmethoxy)carbonyl]-L-leucyl-N-[(1S)-1-formyl-3-methylbutyl]-D-leucinamide;MG-132(R)
• CAS NO: 1211877-36-9
• Molecular Formula: C₂₆H₄₁N₃O₅
• Molecular Weight: 475.62084
• Product Categories: peptides
• Mol File: 1211877-36-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C
• CAS DataBase Reference: (R)-MG132(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-MG132(1211877-36-9)
• EPA Substance Registry System: (R)-MG132(1211877-36-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1211877-36-9(Hazardous Substances Data)

Usage

Description

(R)-MG132 is a potent, reversible, and selective tripeptide aldehyde proteasome inhibitor that plays a crucial role in the ubiquitin-proteasome pathway, which is essential for the selective degradation of intracellular proteins. This pathway is vital for clearing damaged or misfolded proteins and regulating the availability of key proteins involved in controlling inflammatory processes, cell cycle regulation, and gene expression.

Uses

Used in Biochemical Research:
(R)-MG132 is used as a proteasome inhibitor for ubiquitination assays, helping researchers study the role of the ubiquitin-proteasome pathway in various cellular processes.
Used in Pharmaceutical Industry:
(R)-MG132 is used as a research tool for the development of drugs targeting the proteasome, which can have potential therapeutic applications in treating various diseases, including cancer and inflammatory conditions.
Used in Cell Biology:
(R)-MG132 is used as a cell permeable proteasome inhibitor to investigate the effects of proteasome inhibition on cell cycle regulation, apoptosis, and other cellular functions.

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.

Upstream product

• 1211877-30-3 C₂₆H₄₃N₃O₅ 

Relevant articles and documents

Studies of the synthesis of all stereoisomers of MG-132 proteasome inhibitors in the tumor targeting approach

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 two stereoisomers of MG-132 have been reported. Here, we propose a new approach to the synthesis of tripeptide aldehydes based on the Ugi reaction. Chiral, enantiomerically stable 2-isocyano-4-methylpentyl acetates were used as substrates for Ugi reaction resulting in a formation of tripeptide skeletons. Further functionalization of the obtained products led to a synthesis of tripeptide aldehydes. All stereoisomers of MG-132 were synthesized and studied as potential inhibitors of chymotrypsin-like, trypsin-like, and peptidylglutamyl peptide hydrolyzing activities of proteasome. These studies demonstrated the influence of absolute configuration of chiral aldehydes on the cytostatic/cytotoxic effects of the synthesized compounds and revealed that only (S,R,S)-(-)-2 stereoisomer is a more potent. proteasome inhibitor than MG-132.