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L6785

Sigma-Aldrich

Lactacystin

≥90% (HPLC), powder, proteosome inhibitor

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About This Item

Fórmula empírica (notación de Hill):
C15H24N2O7S
Número de CAS:
133343-34-7
Peso molecular:
376.43
Número MDL:
MFCD01076525
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
24896445
NACRES:
NA.77

Nombre del producto

Lactacystin, ≥90% (HPLC)

Nivel de calidad

200

Ensayo

≥90% (HPLC)

Formulario

powder

potencia

4 nM Ki (proteasome inhibitor)

solubilidad

water: 10 mg/mL, clear, colorless

temp. de almacenamiento

−20°C

cadena SMILES

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

Clave InChI

DAQAKHDKYAWHCG-RWTHQLGUSA-N

Descripción general

Lactacystin is an antibiotic and a metabolite of Streptomyces spp.

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
MKCT8161
MKCL8926
MKCF1940
MKCC0039
MKBV3037V

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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)
Differential regulation of MHC II and invariant chain expression during maturation of monocyte-derived dendritic cells
Landsverk O J B, et al.
Journal of Leukocyte Biology, 91(5), 729-737 (2012)
Dallas S Shi et al.
The Journal of clinical investigation, 124(9), 3757-3766 (2014-07-26)
The proteasome inhibiter bortezomib has been successfully used to treat patients with relapsed multiple myeloma; however, many of these patients become thrombocytopenic, and it is not clear how the proteasome influences platelet production. Here we determined that pharmacologic inhibition of
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