| Identification | Back Directory | [Name]
(R)-MG132 | [CAS]
1211877-36-9 | [Synonyms]
(R)-MG132
MG-132(R)
MG-132(S,R,S)
(S,R,S)-(-)-MG-132
Z-Leu-D-leu-leu-al
Cbz-L-leu-D-leu-L-leu-H
N-[(Phenylmethoxy)carbonyl]-L-leucyl-N-[(1S)-1-formyl-3-methylbutyl]-D-leucinamide
D-Leucinamide, N-[(phenylmethoxy)carbonyl]-L-leucyl-N-[(1S)-1-formyl-3-methylbutyl]-
benzyl N-[(2S)-4-methyl-1-[[(2R)-4-methyl-1-[[(2S)-4-methyl-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]carbamate | [EINECS(EC#)]
202-303-5 | [Molecular Formula]
C26H41N3O5 | [MDL Number]
MFCD28580122 | [MOL File]
1211877-36-9.mol | [Molecular Weight]
475.62 |
| Chemical Properties | Back Directory | [Boiling point ]
682.0±55.0 °C(Predicted) | [density ]
1.073±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 25 mg/ml | [form ]
powder | [pka]
11.14±0.46(Predicted) | [color ]
White to off-white | [InChIKey]
MQUQNJIRJAJICL-RJGXRXQPSA-N | [SMILES]
C(N)(=O)[C@@H](CC(C)C)N(C(=O)[C@H](CC(C)C)NC(OCC1=CC=CC=C1)=O)[C@H](C=O)CC(C)C |
| Hazard Information | Back Directory | [Description]
The ubiquitin-proteasome pathway plays an integral role in the selective degradation of intracellular proteins. While important for clearing damaged or mis-folded proteins, this proteolytic pathway also regulates the availability of key proteins involved in the control of inflammatory processes, cell cycle regulation, and gene expression.1,2 (R)-MG132 is a potent, reversible, and cell permeable proteasome inhibitor. After treatment for one hour at 100 nM, it inhibits 50% and 31% of proteasome activity in lysates of J558L multiple myeloma cells and EMT6 breast cancer cells, respectively.3 The (R)-MG132 stereoisomer is a more effective inhibitor of chymotrypsin-like (ChTL), trypsin-like (TL), and peptidylglutamyl peptide hydrolyzing proteasome (PGPH) activities compared to (S)-MG132 (IC50s = 0.22 versus 0.89 μM (ChTL); 34.4 versus 104.43 μM (TL); 2.95 versus 5.70 μM (PGPH), respectively).3 | [Uses]
(R)-MG-132 is a potent, reversible and selective tripeptide aldehyde proteasome inhibitor. | [Uses]
(R)-MG132 has been used in ubiquitination assay and is used as a proteasome inhibitor. | [Definition]
ChEBI: D-leucinamide, n-[(phenylmethoxy)carbonyl]-l-leucyl-n-[(1s)-1-formyl-3-methylbutyl]- is a peptide. | [Biochem/physiol Actions]
MG132 (carbobenzoxy-Leu-Leu-leucinal) is a tri-peptide aldehyde. It possesses antitumor activity and boosts cytostatic/cytotoxic effects of chemo- and radiotherapy. (R)-MG132 is a potent, membrane-permeable proteasome inhibitor. It can inhibit proteasome activity in lysates of J558L multiple myeloma cells and EMT6 breast cancer cells. The (R)-MG132 stereoisomer is a more effective inhibitor of chymotrypsin-like (ChTL), trypsin-like (TL), and peptidylglutamyl peptide hydrolyzing proteasome (PGPH) activities than the (S)-MG132. | [storage]
Store at -20°C | [References]
[1] D H LEE A L G. Proteasome inhibitors: valuable new tools for cell biologists.[J]. Trends in Cell Biology, 1998, 8 10: 397-403. DOI: 10.1016/s0962-8924(98)01346-4
[2] MICHA? MROCZKIEWICZ. Studies of the Synthesis of All Stereoisomers of MG-132 Proteasome Inhibitors in the Tumor Targeting Approach[J]. Journal of Medicinal Chemistry, 2010, 53 4: 1509-1518. DOI: 10.1021/jm901619n
[3] YA-JU CHANG. Cyclic Stretch Facilitates Myogenesis in C2C12 Myoblasts and Rescues Thiazolidinedione-Inhibited Myotube Formation[J]. Frontiers in Bioengineering and Biotechnology, 2016, 4 1. DOI: 10.3389/fbioe.2016.00027 |
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