Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C26H41N3O5 |
| Molecular Weight | 475.6208 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)C[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1)C=O
InChI
InChIKey=TZYWCYJVHRLUCT-VABKMULXSA-N
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
| Molecular Formula | C26H41N3O5 |
| Molecular Weight | 475.6208 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
MG-132, also known as carbobenzoxy-Leu-Leu-leucinal, is a peptide aldehyde, which effectively blocks the proteolytic activity of the 26S proteasome complex. It also strongly inhibited calpain activity in vitro. MG-132 is used as a tool for perturbing the proteasome-regulated degradation of intracellular proteins.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Differential inhibition of calpain and proteasome activities by peptidyl aldehydes of di-leucine and tri-leucine. | 1996 Mar |
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| Potent and selective inhibitors of the proteasome: dipeptidyl boronic acids. | 1998 Feb 17 |
|
| Proteasome inhibition interferes with gag polyprotein processing, release, and maturation of HIV-1 and HIV-2. | 2000 Nov 21 |
|
| Potential of the proteasomal inhibitor MG-132 as an anticancer agent, alone and in combination. | 2001 Nov-Dec |
|
| A novel structural class of potent inhibitors of NF-kappa B activation: structure-activity relationships and biological effects of 6-aminoquinazoline derivatives. | 2003 Sep 1 |
|
| Inhibition of the proteasome reduces transfer-induced diabetes in nonobese diabetic mice. | 2004 Jul-Aug |
|
| Proteasome-dependent degradation of cytochromes P450 2E1 and 2B1 expressed in tetracycline-regulated HeLa cells. | 2004 Sep 15 |
|
| Modulation of IgE-dependent COX-2 gene expression by reactive oxygen species in human neutrophils. | 2006 Jul |
|
| Optimization of subsite binding to the beta5 subunit of the human 20S proteasome using vinyl sulfones and 2-keto-1,3,4-oxadiazoles: syntheses and cellular properties of potent, selective proteasome inhibitors. | 2006 May 18 |
|
| Inhibition of agonist-induced down-regulation of the delta-opioid receptor with a proteasome inhibitor attenuates opioid tolerance in human embryonic kidney 293 cells. | 2007 Mar |
|
| The effect of MG132, a proteasome inhibitor on HeLa cells in relation to cell growth, reactive oxygen species and GSH. | 2009 Jul |
|
| Proteasome inhibitors block HIV-1 replication by affecting both cellular and viral targets. | 2009 Jul 17 |
|
| Broad-spectrum antimalarial activity of peptido sulfonyl fluorides, a new class of proteasome inhibitors. | 2013 Aug |
|
| TDP-43 causes differential pathology in neuronal versus glial cells in the mouse brain. | 2014 May 15 |
Patents
Sample Use Guides
Dose-dependent inhibition of cell growth was observed in HeLa cells with an IC50 of approximately 5 microM MG-132 for 24 h. DNA flow cytometric analysis indicated that treatment with MG132 induced S, G2-M or non-specific phase arrests of the cell cycle dose-dependently. Treatment with MG132 induced apoptosis in a dose-dependent manner, as evidenced by sub-G1 cells and annexin V staining cells. Treatment with MG132 also induced the loss of mitochondrial membrane potential in HeLa cells. MG132 inhibited the growth of HeLa cells via inducing the cell cycle arrest as well as triggering apoptosis.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:34:32 GMT 2023
by
admin
on
Sat Dec 16 09:34:32 GMT 2023
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| Record UNII |
RF1P63GW3K
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| Record Status |
Validated (UNII)
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| Record Version |
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RF1P63GW3K
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133407-82-6
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462382
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C128633
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MG132
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DTXSID3042639
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75142
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