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

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

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.