MG132

MG132
Names
	IUPAC name Benzyl N-[(2S)-4-methyl-1-[[(2S)-4-methyl-1-[[(2S)-4-methyl-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]carbamate
	Other names N-Benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal; Z-Leu-Leu-Leu-al
Identifiers
CAS Number	133407-82-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	406728 ;
PubChem CID	462382;
	InChI 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 Key: TZYWCYJVHRLUCT-VABKMULXSA-N ;
	SMILES CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1;
Properties
Chemical formula	C26H41N3O5
Molar mass	475.63 g·mol−1
Appearance	White solid
Solubility	100 mM in EtOH and DMSO
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

MG132 is a potent, reversible, and cell-permeable proteasome inhibitor ^[1] (K_i = 4 nM). It belongs to the class of synthetic peptide aldehydes ^[2]. It reduces the degradation of ubiquitin-conjugated proteins in mammalian cells and permeable strains of yeast by the 26S complex without affecting its ATPase or isopeptidase activities. MG132 activates c-Jun N-terminal kinase (JNK1), which initiates apoptosis. MG132 also inhibits NF-κB activation with an IC₅₀ of 3 µM and prevents β-secretase cleavage.

References

↑ Hayashi M, Saito Y, Kawashima S (Jan 31, 1992). "Calpain activation is essential for membrane fusion of erythrocytes in the presence of exogenous Ca2+". Biochem Biophys Res Commun. 182 (2): 939–946. PMID 1734892.
↑ Ito A, Takahashi R, Muira C, Baba Y (1975). "Synthetic Study of Peptide Aldehydes". Chemical and Pharmaceutical Bulletin. 12 (23): 2106–3113. doi:10.1248/cpb.37.3229. PMID 8987871.

"MG-132". merck-chemicals.com.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[Hayashi-1] Hayashi M, Saito Y, Kawashima S (Jan 31, 1992). "Calpain activation is essential for membrane fusion of erythrocytes in the presence of exogenous Ca2+". Biochem Biophys Res Commun. 182 (2): 939–946. PMID 1734892.

[Ito-2] Ito A, Takahashi R, Muira C, Baba Y (1975). "Synthetic Study of Peptide Aldehydes". Chemical and Pharmaceutical Bulletin. 12 (23): 2106–3113. doi:10.1248/cpb.37.3229. PMID 8987871.