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Merck

L6785

Lactacystin

≥90% (HPLC), powder, proteosome inhibitor

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About This Item

Empirical Formula (Hill Notation):
C15H24N2O7S
CAS Number:
Molecular Weight:
376.43
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Assay:
≥90% (HPLC)
Form:
powder
Quality level:
Technical Service
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Product Name

Lactacystin, ≥90% (HPLC)

Quality Level

assay

≥90% (HPLC)

form

powder

potency

4 nM Ki (proteasome inhibitor)

solubility

water: 10 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

CC(C)[C@H](O)[C@]1(NC(=O)[C@H](C)[C@@H]1O)C(=O)SC[C@H](NC(C)=O)C(O)=O

InChI

1S/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)/t7-,9+,10+,11+,15-/m1/s1

InChI key

DAQAKHDKYAWHCG-RWTHQLGUSA-N

General description

Lactacystin is an antibiotic and a metabolite of Streptomyces spp.

Application

Lactacystin has been used:
  • as a proteasome inhibitor to inhibit protein degradation
  • to inhibit proteasomal activity of cells for live cell imaging
  • to block proteasomal proteolysis in human monocyte-derived dendritic cells (MoDCs) for 24 h
  • to provide unilateral injection to animals to induce nigrostriatal lesions

Biochem/physiol Actions

Lactacystin can block the development of cell cycle and stimulate differentiation in a murine neuroblastoma cell line. It can serve as a precursor for clasto-lactacystin β-lactone. Cell-permeable and irreversible proteasome inhibitor (Ki = 4nM). Inhibits NF-kB activation (IC50 = 10mM). Induces neurite outgrowth in neuro2A mouse neuroblastoma cells.


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

L6785-.2MG-PW: + L6785-.2MG: + L6785-VAR: + L6785-BULK:

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Articles

DISCOVER Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

Discover definitions and uses for irreversible inhibitors including the types of irreversible inhibitors: suicide inhibitors, heavy metal inhibitors, and time-dependent inhibitors.

Related Content

Select different protease inhibitor types based on your needs to prevent protein degradation during isolation and characterization and safeguard proteins in sample prep.

タンパク質の単離と特性解析におけるタンパク質分解を予防して、サンプル調製でタンパク質を保護するために、ニーズに応じてさまざまなプロテアーゼ阻害剤を選択しましょう。

View All Related Content

Mechanistic Studies on the Inactivation of the Proteasome by Lactacystin A CENTRAL ROLE FOR clasto-LACTACYSTIN beta-LACTONE
Dick L R, et al.
The Journal of Biological Chemistry, 271(13), 7273-7276 (1996)
The development and pharmacology of proteasome inhibitors for the management and treatment of cancer
Ruggeri B, et al.
Advances in Pharmacology, 57(13), 91-135 (2009)
Cannabinoid receptor-induced neurite outgrowth is mediated by Rap1 activation through Galphao/i-triggered proteasomal degradation of Rap1GAPII
Jordan J D, et al.
The Journal of Biological Chemistry, 280(12), 11413-11421 (2005)