474790

Sigma-Aldrich

MG-132 - CAS 133407-82-6 - Calbiochem

A cell-permeable, potent, reversible proteasome inhibitor (Ki = 4 nM).

Synonym(s):
MG-132, Z-Leu-Leu-Leu-al, Carbobenzoxy-L-leucyl-L-leucyl-L-leucinal, Z-LLL-CHO, Proteasome Inhibitor XI
Empirical Formula (Hill Notation):
C26H41N3O5
CAS Number:
Molecular Weight:
475.62
MDL number:
NACRES:
NA.77
Pricing and availability is not currently available.

storage conditions

-20C

Quality Level

assay

≥98% (HPLC)

form

solid

mfr. no.

Calbiochem®

storage condition

OK to freeze

color

white

solubility

DMSO: 20 mg/mL
ethanol: 20 mg/mL

shipped in

ambient

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

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Amino Acid Sequence

Z-Leu-Leu-Leu-al

General description

Potent, reversible, and cell-permeable proteasome inhibitor (Ki = 4 nM). Reduces the degradation of ubiquitin-conjugated proteins in mammalian cells and permeable stains 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-kB activation (IC50 = 3 µM). Also reported to increases the survival rate of mesenchymal stem cells following their transplantation.
A potent, reversible, and cell-permeable proteasome inhibitor (Ki = 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.

Packaging

1, 5, 10 mg in Plastic ampoule

Biochem/physiol Actions

Target IC50: 3 µM against NF-κB activation
Primary Target
proteasome
Product does not compete with ATP.
Reversible: yes
Cell permeable: yes
Target Ki: 4 nM against proteasome

Warning

Toxicity: Standard Handling (A)

Sequence

Z-Leu-Leu-Leu-CHO

Reconstitution

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.

Legal Information

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

WGK Germany

WGK 3

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