L6785

Sigma-Aldrich

Lactacystin

≥90% (HPLC)

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

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_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
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...
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)
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