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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H42BN3O6
Molecular Weight 491.428
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PS-III

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)B(O)O

InChI

InChIKey=MWKOOGAFELWOCD-FKBYEOEOSA-N
InChI=1S/C25H42BN3O6/c1-16(2)12-20(24(31)29-22(26(33)34)14-18(5)6)27-23(30)21(13-17(3)4)28-25(32)35-15-19-10-8-7-9-11-19/h7-11,16-18,20-22,33-34H,12-15H2,1-6H3,(H,27,30)(H,28,32)(H,29,31)/t20-,21-,22-/m0/s1

HIDE SMILES / InChI
MG-262, a boronic peptide acid, is a potent proteasome inhibitor that selectively and reversibly inhibits the chymotryptic activity of the proteasome. It consists of a peptide and boronic acid moiety which are functional to proteasome inhibition.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.00115 µM [Ki]
24.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Potent and selective inhibitors of the proteasome: dipeptidyl boronic acids.
1998 Feb 17
Role of the proteasome in the regulation of fetal fibronectin secretion in human placenta.
2001 Sep
Proteasome inhibitors stimulate activator protein-1 pathway via reactive oxygen species production.
2002 Aug 28
Proteasome inhibitors induce peroxisome proliferator-activated receptor transactivation through RXR accumulation and a protein kinase C-dependent pathway.
2005 Mar 10
Identification of the proteasome inhibitor MG262 as a potent ATP-dependent inhibitor of the Salmonella enterica serovar Typhimurium Lon protease.
2006 Jul 11
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
Retinol decreases beta-catenin protein levels in retinoic acid-resistant colon cancer cell lines.
2007 Apr
Defective DNA strand break repair causes chromosomal instability and accelerates liver carcinogenesis in mice.
2008 Jun
Lon peptidase 1 (LONP1)-dependent breakdown of mitochondrial 5-aminolevulinic acid synthase protein by heme in human liver cells.
2011 Jul 29
Scutellarin inhibits high glucose-induced and hypoxia-mimetic agent-induced angiogenic effects in human retinal endothelial cells through reactive oxygen species/hypoxia-inducible factor-1α/vascular endothelial growth factor pathway.
2014 Sep
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
MG-262 is capable of reducing the viability of human nasal mucosa and polyp fibroblasts (IC50 values: 48 h, 11 nM; 72 h, 4 nM), and inducing cell death via loss of mitochondrial membrane potential, caspase-3 and poly(ADP-ribose) polymerase activation (treatment with 50 nM MG262 for 24 h did not result in the expression of cleaved caspase-3, or its substrate PARP, in any fibroblast line tested).
Name Type Language
PS-III
Common Name English
MG-262
Code English
L-LEUCINAMIDE, N-((PHENYLMETHOXY)CARBONYL)-L-LEUCYL-N-((1R)-1-BORONO-3-METHYLBUTYL)-
Systematic Name English
L-LEUCINAMIDE, N-((PHENYLMETHOXY)CARBONYL)-L-LEUCYL-N-(1-BORONO-3-METHYLBUTYL)-, (R)-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID80170795
Created by admin on Fri Dec 15 21:50:26 GMT 2023 , Edited by admin on Fri Dec 15 21:50:26 GMT 2023
PRIMARY
CAS
179324-22-2
Created by admin on Fri Dec 15 21:50:26 GMT 2023 , Edited by admin on Fri Dec 15 21:50:26 GMT 2023
PRIMARY
PUBCHEM
490002
Created by admin on Fri Dec 15 21:50:26 GMT 2023 , Edited by admin on Fri Dec 15 21:50:26 GMT 2023
PRIMARY
FDA UNII
549V4DP94W
Created by admin on Fri Dec 15 21:50:26 GMT 2023 , Edited by admin on Fri Dec 15 21:50:26 GMT 2023
PRIMARY