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L6785

Sigma-Aldrich

Lactacystin

≥90% (HPLC)

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Empirical Formula (Hill Notation):
C15H24N2O7S
CAS Number:
Molecular Weight:
376.43
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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This Item
B5507H6649426100
vibrant-m

L6785

Lactacystin

vibrant-m

426100

Lactacystin, Synthetic

form

powder

form

crystalline

form

powder

form

solid

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

solubility

water: 10 mg/mL, clear, colorless

solubility

H2O: 20 mg/mL

solubility

DMSO: 7.5 mg/mL (DMSO stock solution can be diluted in phosphate buffered saline. The ratio of buffer:DMSO should be greater than 500:1.)

solubility

DMSO: 50 mg/mL, water: soluble

potency

4 nM Ki (proteasome inhibitor)

potency

-

potency

-

potency

-

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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)
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)
Evolution of extra-nigral damage predicts behavioural deficits in a rat proteasome inhibitor model of Parkinson's disease
Vernon A C, et al.
PLoS ONE, 6(2), e17269-e17269 (2011)
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
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)

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