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Z-Leu-Leu-Leu-B(OH)2 (MG262)

Product Name
Z-Leu-Leu-Leu-B(OH)2 (MG262)
CAS No.
179324-22-2
Chemical Name
Z-Leu-Leu-Leu-B(OH)2 (MG262)
Synonyms
Z-Leu-Leu-Leu-B(OH)2 (MG262);Proteasome Inhibitor III - Calbiochem;L-Leucinamide, N-[(phenylmethoxy)carbonyl]-L-leucyl-N-[(1R)-1-borono-3-methylbutyl]-;[(1R)-3-methyl-1-[[(2S)-4-methyl-2-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]pentanoyl]amino]butyl]boronic acid
CBNumber
CB71562203
Molecular Formula
C25H42BN3O6
Formula Weight
491.43
MOL File
179324-22-2.mol
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Z-Leu-Leu-Leu-B(OH)2 (MG262) Property

Density 
1.101±0.06 g/cm3(Predicted)
storage temp. 
-20C
solubility 
≥24.57 mg/mL in DMSO; insoluble in H2O; ≥96.4 mg/mL in EtOH
form 
White solid
pka
9.69±0.43(Predicted)
color 
White to off-white
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
539163-M
Product name
Proteasome Inhibitor III - Calbiochem
Purity
The Proteasome Inhibitor III controls the biological activity of Proteasome. This small molecule/inhibitor is primarily used for Protease Inhibitors applications.
Packaging
100μg
Price
$364
Updated
2023/01/07
Cayman Chemical
Product number
10008311
Product name
Z-Leu-Leu-Leu-B(OH)2
Packaging
200μg
Price
$299
Updated
2024/03/01
Cayman Chemical
Product number
10008311
Product name
Z-Leu-Leu-Leu-B(OH)2
Packaging
1mg
Price
$1189
Updated
2024/03/01
American Custom Chemicals Corporation
Product number
INB0000203
Product name
MG-262
Purity
95.00%
Packaging
5MG
Price
$500.49
Updated
2021/12/16
ApexBio Technology
Product number
A8179
Product name
MG-262
Packaging
5mg
Price
$700
Updated
2021/12/16
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Z-Leu-Leu-Leu-B(OH)2 (MG262) Chemical Properties,Usage,Production

Uses

MG-262 (Z-Leu-Leu-LeuB(OH)2; ZL3B) is a reversible proteasome inhibitor. MG-262 down-regulates VEGF receptor Flt-1. MG-262 inhibits cell growth and induces apoptosis in malignant cells. MG-262 induces reactive oxygen species (ROS). MG-262 can be used for anti-cancer study[1][2][3][4][5].

General Description

A boronic acid-based, reversible proteasome inhibitor that is structurally similar to MG-132 (Cat. No. 474790) but displays much higher potency (Ki = 0.03 nM versus 4 nM for MG-132).

Biological Activity

mg-262 (also known as z-leu-leu-leu-b(oh)2), 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. according to previous studies, mg-262 is capable of reducing the viability of nasal mucosa and polyp fibroblasts, provoking cell growth arrest, inhibiting dna replication and retinoblastoma phosphorylation, increasing expression of the cell cycle inhibitor p21 and p27, and inducing cell death via loss of mitochondrial membrane potential, caspase-3 and poly(adp-ribose) polymerase activation, induction of c-jun phosphorylation and mitogen-activated protein kinase phosphatase-1 expression.laura pujols, laura fernandez-bertolin, mireya fuentes-prado, isam alobid, jordi roca-ferrer, neus agell, joaquim mullol, and cesar picado. proteasome inhibition reduces proliferation, collagen expression, and inflammatory cytokine production in nasal mucosa and polyp fibroblasts. the journal of pharmacology and experimental therapeutics 2012; 343:184-197hilary frase, jason hudak, and irene lee. identification of the proteasome inhibitor mg262 as a potent atp-dependent inhibitor of the salmonella enteric serovar typhimurium lon protease. biochemistry 2006; 45 (27): 8264-8274

Biochem/physiol Actions

Target Ki: 30 pM against proteasome

in vivo

MG-262 (5 μmol/kg (2.5 mg/kg); i.v.; 20 hours before collecting tissue samples) accumulates GFPdgn protein[4].
MG-262 (1-5 μmol/kg (0.5-2.5 mg/kg); i.p.; 20 h before the test) accumulates the GFP reporter in the liver, indicating substantial impairment of the ubiquitin/proteasome system in UbG76V-GFP/1 mice[5].

Animal Model:UbG76V-GFP/1 mice (The transgenic construct was injected into fertilized CBA × C57BL/6 F1 oocytes. Transgenic founders were backcrossed to C57BL/6 mice)[5]
Dosage:1, 5 μmol/kg (0.5, 2.5 mg/kg)
Administration:Intraperitoneal injection (i.p.); 20 h before test
Result:Fluorescent cells were detected exclusively in the livers, resulted in accumulation of GFP in the vast majority of hepatocytes distributed throughout the live.
A dose-dependent decrease of the chymotrypsin-like activity of the proteasome was observed in lysates of the liver, kidney and spleen.
Animal Model:Transgenic mice (ubiquitously expresses a surrogate protein substrate for the Ubiquitin-proteasome system, referred to as GFPdgn)[4]
Dosage:5 μmol/kg (2.5 mg/kg)
Administration:Intravenous injection (i.v.); 20 h before the tissue samples were collected
Result:Inhibited chymotryptic activity in the heart, lungs, skeletal (Sk.) muscle, and liver by 50-75%.
GFPdgn levels in all the indicated organs clearly displayed significant increases.

References

[1] Mezquita J, et al. Down-regulation of Flt-1 gene expression by the proteasome inhibitor MG262. J Cell Biochem. 2003 Aug 15;89(6):1138-47. DOI:10.1002/jcb.10587
[2] Wu HM, et al. Proteasome inhibitors stimulate activator protein-1 pathway via reactive oxygen species production. FEBS Lett. 2002 Aug 28;526(1-3):101-5. DOI:10.1016/s0014-5793(02)03151-4
[3] Huang H, et al. Gambogic acid enhances proteasome inhibitor-induced anticancer activity. Cancer Lett. 2011 Feb 28;301(2):221-8. DOI:10.1016/j.canlet.2010.12.015
[4] Kumarapeli AR, et al A novel transgenic mouse model reveals deregulation of the ubiquitin-proteasome system in the heart by doxorubicin. FASEB J. 2005 Dec;19(14):2051-3. DOI:10.1096/fj.05-3973fje
[5] Lindsten K, et al. A transgenic mouse model of the ubiquitin/proteasome system. Nat Biotechnol. 2003 Aug;21(8):897-902. DOI:10.1038/nbt851

Z-Leu-Leu-Leu-B(OH)2 (MG262) Preparation Products And Raw materials

Raw materials

Preparation Products

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Z-Leu-Leu-Leu-B(OH)2 (MG262) Suppliers

China 28 United Kingdom 1 United States 4 Global 33
Sigma-Aldrich
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021-61415566 800-8193336
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Shanghai EFE Biological Technology Co., Ltd.
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Amadis Chemical Company Limited
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TargetMol Chemicals Inc.
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ChemeGen(Shanghai) Biotechnology Co.,Ltd.
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MedBioPharmaceutical Technology Inc
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Zhengzhou Akem Chemical Co., Ltd
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TargetMol Chemicals Inc.
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marketing@tsbiochem.com
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RD International Technology Co., Limited
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market@ubiochem.com
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Adipogen Life Sciences
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179324-22-2, Z-Leu-Leu-Leu-B(OH)2 (MG262)Related Search:

L-Leu-Leu-Leu

  • Z-Leu-Leu-Leu-B(OH)2 (MG262)
  • [(1R)-3-methyl-1-[[(2S)-4-methyl-2-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]pentanoyl]amino]butyl]boronic acid
  • Proteasome Inhibitor III - Calbiochem
  • L-Leucinamide, N-[(phenylmethoxy)carbonyl]-L-leucyl-N-[(1R)-1-borono-3-methylbutyl]-
  • 179324-22-2
  • C25H42BN3O6