MG-132 [Z-Leu-Leu-Leu-CHO] A proteasome and NF-κB inhibitor

MG-132 [Z-Leu-Leu-Leu-CHO] (CAS 133407-82-6)

MG-132 [Z-Leu-Leu-Leu-CHO] | CAS 133407-82-6 is rated 5.0 out of 5 by 2.
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Synonym: Z-LLL-a; N-[(Phenylmethoxy)carbonyl]-L-leucyl-N-[(1S)-1-formyl-3-methylbutyl]-L-leucinamide; Carbobenzoxy-L-leucyl-L-leucyl-L-leucinal
Application: A proteasome and NF-κB inhibitor
CAS Number: 133407-82-6
Purity: >98%
Molecular Weight: 475.62
Molecular Formula: C26H41N3O5
* Refer to Certificate of Analysis for lot specific data (including water content).
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MG-132 [Z-Leu-Leu-Leu-CHO] is a proteasome inhibitor, used as a tool for perturbing the proteasome-regulated degradation of intracellular proteins. These proteins processed by the proteasome are involved in inflammatory processes and cell cycle regulation, presenting broad relevance for aldehydic proteasome inhibitors of this type. MG-132 suppresses NF-κB activation (at 10 μM) by preventing IκB degradation (IC50=3 μM), which blocks the transcription factor from providing chemoresistance to cancer cells. It is also an an inhibitor of calpain. MG-132 [Z-Leu-Leu-Leu-CHO] is an inhibitor of 26S Proteasome and an activator of JNK1, c-Jun and c-Fos.


References

1. Lee, D.H. and Goldberg, A.L. 1998. Trends Cell Biol. 8: 397-403. PMID: 9789328
2. Arlt, A., et al. 2001. Oncogene. 20: 859-868. PMID: 11314019
3. Elliott, P.J., et al. 2003. J. Mol. Med. 81: 235-245. PMID: 12700891
4. Vivier, M., et al. 2008. J. Med. Chem. 51: 1043-1047. PMID: 18237109
5. Ye, X. et al. 2014. PLoS Pathog. 10(4): e1004070. PMID: 24722419

Physical State :
Solid
Sequence :
Z-Leu-Leu-Leu-CHO
Solubility :
Soluble in ethanol (100 mM), and DMSO (100 mM).
Storage :
Store at -20° C
Melting Point :
96-99° C
Boiling Point :
~682.0° C at 760 mmHg (Predicted)
Density :
~1.1 g/cm3 (Predicted)
Refractive Index :
n20D 1.51
Optical Activity :
α20D -65.5°, c = 1 in chloroform
IC50 :
NF-κB activation: IC50 = 3 µM; Suc-LLVY-AMC cleaving activity of proteasome: IC50 = 0.85 µM; Z-LLL-AMC cleaving activity of proteasome: IC50 = 0.1 µM; calpain: IC50 = 1.2 µM; IκBα degradation: IC50 = 3 µM
Ki Data :
proteasome: Ki= 4 nM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
OH2824610
PubChem CID :
462382
MDL Number :
MFCD00674886
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

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Certificate of Analysis

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MG-132 [Z-Leu-Leu-Leu-CHO]  Product Citations

See how others have used MG-132 [Z-Leu-Leu-Leu-CHO]. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 52 total

PMID: # 28981087  van Raam, BJ. et al. 2017. Cell Death Dis. 8: e3069.

PMID: # 28475172  Lähdeniemi, IAK. et al. 2017. Cell death and differentiation. 24: 984-996.

PMID: # 27060717  Wan, XK. et al. 2016. Helicobacter.

PMID: # 25914292  Lee, HE. et al. 2016. Head & neck. 38 Suppl 1: E761-70.

PMID: # 27151455  Kim, SJ. et al. 2016. Exp. Mol. Med. 48: e231.

PMID: # 26728942  Guo, Z. et al. 2016. Nat Commun. 7: 10307.

PMID: # 25622294  Silva, GM. et al. 2015. Nat. Struct. Mol. Biol. 22: 116-23.

PMID: # 26231201  Liu, Y. et al. 2015. FASEB J. 29: 4829-39.

PMID: # 26183205  Liu, Y. et al. 2015. FEBS Lett. 589: 2233-40.

PMID: # 25500897  Fiebiger, BM. et al. 2015. European journal of immunology. 45: 716-27.

Citations 1 to 10 of 52 total

What is the appearance of the compound?

Asked by: two2igm05
Thank you for your question. MG-132 [Z-Leu-Leu-Leu-CHO], sc-201270, is a crystalline solid.
Answered by: Chemical Support 4
Date published: 2017-03-15
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Rated 5 out of 5 by from Good quality Good quality, worked well in cell culture studies.
Date published: 2015-10-16
Rated 5 out of 5 by from Ye Ye, X. et al. (PubMed 24722419) used MG-132 [Z-Leu-Leu-Leu-CHO], a potent, reversible and selective proteasome inhibitor, to confirm the involvement of ubiquitin-proteasome pathway in miR-21 mediated desmin degradation. MG-132 eliminated the effect of miR-21 on desmin downregulation, indicating that miR-21 promotes desmin degradation through the ubiquitin-proteasome pathway. -SCBT Publication Review
Date published: 2015-06-18
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