(R)-MG132

(R)-MG132 is a potent, reversible, and cell permeable proteasome inhibitor.

Product information

CAS Number: 1211877-36-9

Molecular Weight: 489.65

Formula: C27H43N3O5

Synonym:

Z-Leu-D-Leu-Leu-al

(S, R, S)-(-)-MG-132

Chemical Name: N-[(phenylmethoxy)carbonyl]-L-leucyl-N-[(1R)-1-formyl-3-methylbutyl]-L-leucinamide

Smiles: CC(C)C[C@H](NC(=O)OCC1C=CC=CC=1)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CC=O)CC(C)C

InChiKey: HWFLPOLDRUQRFC-SMIHKQSGSA-N

InChi: InChI=1S/C27H43N3O5/c1-18(2)14-22(12-13-31)28-25(32)23(15-19(3)4)29-26(33)24(16-20(5)6)30-27(34)35-17-21-10-8-7-9-11-21/h7-11,13,18-20,22-24H,12,14-17H2,1-6H3,(H,28,32)(H,29,33)(H,30,34)/t22-,23-,24+/m1/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO: 90 mg/mL(189.22 mM). Water: Insoluble.

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

(R)-MG-132, the stereoisomer of MG-132, is studied as a potential inhibitor of chymotrypsin-like, trypsin-like, and peptidylglutamyl peptide hydrolyzing activities of proteasome[1]. MG-132 and (R)-MG-132 are investigated for inhibition of ChTL, trypsin-like (TL) and peptidylglutamyl peptide hydrolyzing (PGPH) activities of purified 20S proteasomes isolated from human erythrocytes. For MG-132, the IC50s of 0.89 μM, 104.43 μM, and 5.7 μM for ChTL, TL, and PGPH, respectively. For (R)-MG-132, the IC50s of 0.22 μM, 34.4 μM, and 2.95 μM for ChTL, TL, and PGPH, respectively[1].

In Vivo:

Administration of (R)-MG-132 effectively rescues the expression levels and plasma membrane localization of dystrophin, β-dystroglycan, α-bdystroglycan, and α-sarcoglycan in skeletal muscle fibers from mdx mice, reduces muscle membrane damage, and ameliorates the histopathological signs of muscular dystrophy. (R)-MG-132 treatment significantly reduces immobilization-induced skeletal muscle atrophy in mice, by downregulating the muscle-specific ubiquitin ligases atrogin-1/MAFbx and MuRF-1 mRNA.

References:

1. Mroczkiewicz M, et al. Studies of the synthesis of all stereoisomers of MG-132 proteasome inhibitors in the tumor targeting approach. J Med Chem. 2010 Feb 25;53(4):1509-18.
2. Tsubuki S, et al. J Biochem, 1996, 119(3), 572-576.
3. Crawford LJ, et al. Cancer Res, 2006, 66(12), 6379-6386.
4. Bonuccelli G, et al. Am J Pathol, 2003, 163(4), 1663-1675.
5. Li W, et al. Cancer Res, 2007, 67(5), 2247-2255.
6. Caron AZ, et al. BMC Musculoskelet Disord, 2011, 12:185.
7. Fiedler MA, et al. Am J Respir Cell Mol Biol, 1998, 19(2), 259-68.
8. MacLaren AP, et al. Cell Death Differ, 2001, 8(3), 210-218.
9. Diallo JS, et al. Br J Cancer, 2008, 99(10), 1613-1622.
10. Harhouri K, et al. EMBO Mol Med. 2017, 9(9):1294-1313.

Products are for research use only. Not for human use.