ChemicalBook--->CAS DataBase List--->133407-82-6

133407-82-6

133407-82-6 Structure

133407-82-6 Structure
IdentificationBack Directory
[Name]

MG-132
[CAS]

133407-82-6
[Synonyms]

MG-132
Z-LL-CHO
Z-LLL-CHO
(S)-MG132
MG132/MG-132
Z-LEU-LEU-LEU-H
z-leu-leu-leu-al
Z-LEU-LEU-LEU-CHO
Z-LEU-LEU-ALDEHYDE
CALPAIN INHIBITOR IV
N-cbz-leu-leu-leu-al
Z-Leu-Leu-Leu-al,MG132
Calpain inhibitor IV-2
N-CBZ-LEU-LEU-LEUCINAL
Z-LEU-LEU-LEU-ALDEHYDE
Z-LEU-LEU-LEU-H (ALDEHYDE)
PROTEASOME INHIBITOR MG-132
N-carbobenzyloxy-Leu-Leu-Leu-al
MG 132 Calpain inhibitor IV-2
CARBOBENZOXY-L-LEUCYL-L-LEUCYL-LEUCINAL
CARBOBENZOXY-L-LEUCYL-L-LEUCYL-L-LEUCINAL
BENZYLOXYCARBONYL-L-LEUCYL-L-LEUCYL-L-LEUCINAL
benzyloxycarbonylleucyl-leucyl-leucinealdehyde
N-[(PHENYLMETHOXY)CARBONYL]-L-LEUCYL-N-[(1S)-1-FORMYL-3-METHYLBUTYL]-L-LEUCINAMIDE
L-LeucinaMide, N-[(phenylMethoxy)carbonyl]-L-leucyl-N-[(1S)-1-forMyl-3-Methylbutyl]-
benzyl ((S)-4-Methyl-1-(((S)-4-Methyl-1-(((S)-4-Methyl-1-oxopentan-2-yl)aMino)-1-oxopentan-2-yl)aMino)-1-oxopentan-2-yl)carbaMate
N-[(Phenylmethoxy)carbonyl]-L-leucyl-N-[(1S)-1-formyl-3-methylbutyl]-L-leucinamide Calpain inhibitor IV-2 MG 132
[Molecular Formula]

C26H41N3O5
[MDL Number]

MFCD00674886
[MOL File]

133407-82-6.mol
[Molecular Weight]

475.62
Chemical PropertiesBack Directory
[Melting point ]

80-84℃ (DEC.)
[alpha ]

-61~-67°
[Boiling point ]

682.0±55.0 °C(Predicted)
[density ]

1.073
[Fp ]

366℃
[storage temp. ]

−20°C
[solubility ]

methanol: 1 mg/mL
[form ]

solid film
[pka]

11.14±0.46(Predicted)
[color ]

White
[Water Solubility ]

Soluble in ethanol, chloroform, methanol, water.
[Stability:]

Stable for 2 years from date of purchase as supplied. Solutions in DMSO, DMF or ethanol may be stored at -20° for up to 1 week.
[InChIKey]

TZYWCYJVHRLUCT-VABKMULXSA-N
Safety DataBack Directory
[Risk Statements ]

36/37/38
[Safety Statements ]

24/25
[WGK Germany ]

3
[HS Code ]

29242990
Hazard InformationBack Directory
[Biological Activity]

Potent cell-permeable inhibitor of proteasome (IC 50 = 100 nM) and calpain (IC 50 = 1.2 μ M). Inhibits TNF-α-induced NF-κ B activation and I κ B α degradation. Induces neurite outgrowth in PC12 cells and has anticancer properties in vitro .
[Description]

MG-132 (133407-82-6) is a specific inhibitor of the chymotrypsin-like activity of the 20S proteasome (IC50=100 nM with Z-LLL-AMC as substrate).1 Also inhibits calpain (IC50=1.25 μM).1 Suppresses gastric cancer cell proliferation and induces macro-autophagy.2 Activates stress kinases and induces Hsp72.3 Induces neurite outgrowth.1 MG-132 blocks NFκB activation by blocking IκB proteolysis (IC50=3 μM).4 Cell permeable.
[Uses]

A proteasome and NF-κB inhibitor.
[Definition]

ChEBI: A tripeptide that is L-leucyl-L-leucyl-L-leucine in which the C-terminal carboxy group has been reduced to the corresponding aldehyde and the N-terminal amino group is protected as its benzyloxycarbonyl derivative.
[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) and inhibits NF-κB activation (IC50 = 3 μM).
[Biochem/physiol Actions]

Cell permeable: yes
[References]

1) Tsubuki et al. (1996), Differential inhibition of calpain and proteasome activities by peptidyl aldehydes of di-leucine and tri-leucine; J. Biochem.,? 119 572 2) Wu? et al. (2010), Macroautophagy and ERK phosphorylation counteract the antiproliferative effect of proteasome inhibitor in gastric cancer cells; Autophagy, 6 228 3) Meriin? et al. (1998), Proteasome inhibitors activate stress kinases and induce Hsp72. Diverse effects on apoptosis; J. Biol. Chem., 273 6373 4) Fiedler et al. (1998), Inhibition of TNF-alpha-induced NF-kappaB activation and IL-8 release in A549 cells with the proteasome inhibitor MG-132; Am. J. Respir. Cell Mol. Biol., 19 259
Spectrum DetailBack Directory
[Spectrum Detail]

MG-132(133407-82-6)1HNMR
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