Skip to Content
Merck
All Photos(1)

Key Documents

M8699

Sigma-Aldrich

(R)-MG132

(R)-MG132

Synonym(s):

Z-L-Leu-D-Leu-L-Leu-al

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C26H41N3O5
CAS Number:
Molecular Weight:
475.62
UNSPSC Code:
12352200
NACRES:
NA.32
Pricing and availability is not currently available.

Assay

≥98%

Quality Level

solubility

DMSO or DMF: 25 mg/mL

storage temp.

−20°C

SMILES string

CC(C)C[C@@H](C(N[C@H](C(N[C@H](C=O)CC(C)C)=O)CC(C)C)=O)NC(OCC1=CC=CC=C1)=O

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

InChI key

TZYWCYJVHRLUCT-VABKMULXSA-N

Application

(R)-MG132 has been used in ubiquitination assay and is used as a proteasome inhibitor.[1][2][3][4]

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.[5] (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.[5]

Physical form

crystalline solid or supercooled liquid

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

A Mad2-Mediated Translational Regulatory Mechanism Promoting S-Phase Cyclin Synthesis Controls Origin Firing and Survival to Replication Stress.
Gay S, et al.
Molecular Cell, 70(4), 628-638 (2018)
Alternative promotion and suppression of metastasis by JNK2 governed by its phosphorylation.
Hu S, et al.
Oncotarget, 8(34), 56569-56569 (2017)
Studies of the synthesis of all stereoisomers of MG-132 proteasome inhibitors in the tumor targeting approach.
Mroczkiewicz M, et al.
Journal of Medicinal Chemistry, 53(4), 1509-1518 (2010)
Yanling Tao et al.
Oncology letters, 14(6), 6365-6372 (2017-11-23)
Osteosarcoma (OS) is among the most frequently occurring bone tumors, particularly in children. Clinical treatment of OS is limited due to several factors including resistance to chemotherapy drugs and metastasis, and the underlying molecular mechanisms remain unclear. In the present
J Yang et al.
Oncogene, 36(34), 4828-4842 (2017-04-11)
PIM1 is a proto-oncogene, encoding a serine/threonine protein kinase that regulates cell proliferation, survival, differentiation and apoptosis. Previous reports suggest that overexpression of PIM1 can induce cellular senescence. However, the molecular mechanism underlying this process is not fully understood. Here

Questions

1–2 of 2 Questions  
  1. Which cells are utilized to assess the bioactivity of Product No. M8699, also known as (R)-MG132?

    1 answer
    1. The biological activity of product No. M8699, (R)-MG132 was measured using J558L multiple myeloma cells and EMT6 breast cancer cells.

      Helpful?

  2. What is the molarity of a solution with a concentration of 25 mg/ml in DMSO?

    1 answer
    1. The molarity of a 25 mg/ml solution is 0.052 M, which is equivalent to 52 mM. This calculation is based on a substance with a molar mass of 475.62 g/mol, where a 1 M solution is prepared by dissolving 475.62 g in 1 liter.

      Helpful?

Reviews

Active Filters

  1. Newark. NJ, USA
    • Review 1
    • Vote 1
    5 out of 5 stars.

    Worked spot on!!!

    The product worked at 25micromolar concentration for rat neonatal myocytes

    Helpful?

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service