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MG-132 (GMP)

CAT: 0804-HY-13259GSize: 1 EachDry Ice: NoHazardous: No
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Description
MG-132 (GMP) (Z-Leu-Leu-Leu-al (GMP) ) is MG-132 produced by using GMP guidelines. GMP small molecules works appropriately as an auxiliary reagent for cell therapy manufacture. MG-132 (Z-Leu-Leu-Leu-al) is a potent proteasome and calpain inhibitor with IC50s of 100 nM and 1.2 μM, respectively. MG-132 effectively blocks the proteolytic activity of the 26S proteasome complex. MG-132, a peptide aldehyde, also is an autophagy activator. MG-132 also induces apoptosis[1][2][3].
CAS Number
133407-82-6
Product Name Alternative
Z-Leu-Leu-Leu-al (GMP)
UNSPSC
12352005
Target
Apoptosis; Autophagy; Proteasome
Related Pathways
Apoptosis; Autophagy; Metabolic Enzyme/Protease
Field of Research
Cancer
Smiles
O=C(OCC1=CC=CC=C1)N[C@H](C(N[C@@H](CC(C)C)C(N[C@H](C([H])=O)CC(C)C)=O)=O)CC(C)C
Molecular Formula
C26H41N3O5
Molecular Weight
475.62
References & Citations
[1]Harhouri K, et al. MG132-induced progerin clearance is mediated by autophagy activation and splicing regulation. EMBO Mol Med. 2017 Sep;9 (9) :1294-1313. |[2]Fan WH, et al. Proteasome inhibitor MG-132 induces C6 glioma cell apoptosis via oxidative stress. Acta Pharmacol Sin. 2011 May;32 (5) :619-25.|[3]Tsubuki S, et al. Differential inhibition of calpain and proteasome activities by peptidyl aldehydes of di-leucine and tri-leucine. J Biochem. 1996 Mar;119 (3) :572-6.|[4]Fiedler MA, et al. 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. 1998 Aug;19 (2) :259-68. |[5]MacLaren AP, et al. p53-dependent apoptosis induced by proteasome inhibition in mammary epithelial cells. Cell Death Differ. 2001 Mar;8 (3) :210-8. |[6]Han YH, et al. The effect of MG132, a proteasome inhibitor on HeLa cells in relation to cell growth, reactive oxygen species and GSH. Oncol Rep. 2009 Jul;22 (1) :215-21. |[7]Dang L, et al. Proteasome inhibitor MG132 inhibits the proliferation and promotes the cisplatin-inducedapoptosis of human esophageal squamous cell carcinoma cells. Int J Mol Med. 2014 May;33 (5) :1083-8. |[8]Matsumoto Y, et al. Enhanced efficacy against cervical carcinomas through polymeric micelles physically incorporating theproteasome inhibitor MG132. Cancer Sci. 2016 Jun;107 (6) :773-81. |[9]Bonuccelli G, et al. Proteasome inhibitor (MG-132) treatment of mdx mice rescues the expression and membrane localization of dystrophin and dystrophin-associated proteins. Am J Pathol. 2003 Oct;163 (4) :1663-75.
Shipping Conditions
Room temperature
Scientific Category
GMP Small Molecules
Clinical Information
No Development Reported

Chemical Information

MG-132

N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal is 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. It has a role as a proteasome inhibitor. It is an amino aldehyde, a carbamate ester and a tripeptide.

CAS Number133407-82-6
PubChem CID462382
IUPAC Namebenzyl N-[(2S)-4-methyl-1-[[(2S)-4-methyl-1-[[(2S)-4-methyl-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]carbamate
Molecular FormulaC26H41N3O5
Molecular Weight475.6
XLogP4.8
Topological Polar Surface Area114
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count15
Heavy Atom Count34
Formal Charge0
Complexity644
SMILES
CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1
InChI
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
InChIKey
TZYWCYJVHRLUCT-VABKMULXSA-N
Chemical Structure
2D Structure
2D structure of MG-132
CAS: 133407-82-6
CID: 462382
Formula: C26H41N3O5
MW: 475.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight475.6
XLogP34.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count15
Exact Mass475.30462142
Monoisotopic Mass475.30462142
Topological Polar Surface Area114 Ų
Heavy Atom Count34
Formal Charge0
Complexity644
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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