474790

MG-132

≥98% (HPLC), proteasome inhibitor, solid

• Synonym(s): Z-Leu-Leu-Leu-al, Carbobenzoxy-L-leucyl-L-leucyl-L-leucinal, Z-LLL-CHO, Proteasome Inhibitor XI, MG-132
• Empirical Formula (Hill Notation): C₂₆H₄₁N₃O₅
• CAS Number: 133407-82-6
• Molecular Weight: 475.62
• NACRES: NA.77
• UNSPSC Code: 12352200
• MDL number: MFCD00674886
• Assay: ≥98% (HPLC)
• Form: solid
• Storage condition: OK to freeze

Properties

• Product Name: MG-132, A cell-permeable, potent, reversible proteasome inhibitor (K_i = 4 nM).
• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white
• solubility: DMSO: 20 mg/mL, ethanol: 20 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: [H]C(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1
• InChI: 1S/C26H41N3O5/c1-17(2)12-21(15-30)27-24(31)22(13-18(3)4)28-25(32)23(14-19(5)6)29-26(33)34-16-20-10-8-7-9-11-20/h7-11,15,17-19,21-23H,12-14,16H2,1-6H3,(H,27,31)(H,28,32)(H,29,33)/t21-,22-,23-/m0/s1
• InChI key: TZYWCYJVHRLUCT-VABKMULXSA-N

Description

General description

A potent, reversible, and cell-permeable proteasome inhibitor (K_i = 4 nM). Reduces the degradation of ubiquitin-conjugated proteins in mammalian cells and permeable strains of yeast by the 26S complex without affecting its ATPase or isopeptidase activities. Activates c-Jun N-terminal kinase (JNK1), which initiates apoptosis. Inhibits NF-κB activation (IC₅₀ = 3 µM). Also reported to increases the survival rate of mesenchymal stem cells following their transplantation. Prevents β-secretase cleavage. A 10 mM (1 mg/210 µl) solution of MG-132 (Cat. No. 474791) in DMSO is also available. This material is ≥98% pure by HPLC. A material with ≥95% purity by HPLC (Cat. No. 474787) is also available.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
proteasome

Product does not compete with ATP.

Reversible: yes

Target IC₅₀: 3 µM against NF-κB activation

Target K_i: 4 nM against proteasome

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Other Notes

Li, Z.W. et al. 2011. Sheng Li Xue Bao. 63, 525.
Steinhilb, M.L., et al. 2001. J. Biol. Chem.276, 4476.
Meriin, A.B., et al. 1998. J. Biol. Chem. 273, 6373.
Adams, J., and Stein, R. 1996. Ann. Rep. Med. Chem.31, 279.
Klafki, H.W., et al. 1996. J. Biol. Chem.271, 2865.
Lee, D.H., and Goldberg, A.L., 1996. J. Biol. Chem.271, 27280.
Wiertz, E.J., et al. 1996. Cell84, 769.
Jensen, T.J., et al. 1995. Cell 83, 129.
Read, M.A., et al. 1995. Immunity2, 493.
Rock, K.L., et al. 1994. Cell 78, 761.

Z-Leu-Leu-Leu-CHO

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3