(R)-MG132

(R)-MG132 Property

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

pka

11.14±0.46(Predicted)

form 

powder

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

Safety

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H303May be harmfulif swallowed

H320Causes eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P337+P313IF eye irritation persists: Get medical advice/attention.

(R)-MG132 Chemical Properties,Usage,Production

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. (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. 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).

Uses

(R)-MG132 has been used in ubiquitination assay and is used as a proteasome inhibitor.

Uses

(R)-MG-132 is a potent, reversible and selective tripeptide aldehyde 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