L7035

clasto-Lactacystin β-lactone

Name: clasto-Lactacystin β-lactone
Brand: SIGMA

≥95% (HPLC), irreversible proteasome inhibitor, film

Synonym(s):

(1R,4R,5S)-1-[(1S)-1-Hydroxy-2-Methylpropyl]-4-Methyl-6-Oxa-2-Azabicyclo[3.2.0]Heptane-3,7-Dione, Omuralide

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₅NO₄

CAS Number:

154226-60-5

Molecular Weight:

213.23

UNSPSC Code:

12352200

PubChem Substance ID:

24896450

NACRES:

NA.77

MDL number:

MFCD01076526

Product Name

clasto-Lactacystin β-lactone,

SMILES string

[H][C@@]12OC(=O)[C@@]1(NC(=O)[C@@H]2C)[C@@H](O)C(C)C

InChI key

FWPWHHUJACGNMZ-NBBQQVJHSA-N

InChI

1S/C10H15NO4/c1-4(2)6(12)10-7(15-9(10)14)5(3)8(13)11-10/h4-7,12H,1-3H3,(H,11,13)/t5-,6+,7+,10-/m1/s1

assay

≥95% (HPLC)

form

film

solubility

DMSO: soluble 25 mg/mL

storage temp.

−20°C

Quality Level

100

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

Clasto-Lactacystin β-lactone has been used as a proteasomal inhibitor.

Clasto-Lactacystin β-lactone has been used as a protein degradation inhibitor to test its effect on memory improvements in mice. It has also been used as a proteasome inhibitor in human ovarian surface epithelium (HOSE) cells and dendritic cells (DCs).

Biochem/physiol Actions

Cell-permeable and irreversible proteasome inhibitor. Lactacystin acts as a precursor for clasto-lactacystin β-lactone.

Clasto-Lactacystin β-lactone (cLβL) is synthesized from lactacystin. It is cell-permeable and cLβL acts on the N-terminal threonine of subunit proteasome β -subunit X It also inhibits 20S proteasome activity in Haloferax volcanii by acting in the N-threonine residue of the β -type subunits.

pictograms

GHS07

signalword

Warning

hcodes

H319

pcodes

P264 - P280 - P305 + P351 + P338 - P337 + P313

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Synaptic protein degradation underlies destabilization of retrieved fear memory.

Sue-Hyun Lee et al.

Science (New York, N.Y.), 319(5867), 1253-1256 (2008-02-09)

Reactivated memory undergoes a rebuilding process that depends on de novo protein synthesis. This suggests that retrieval is dynamic and serves to incorporate new information into preexisting memories. However, little is known about whether or not protein degradation is involved

Mechanistic studies on the inactivation of the proteasome by lactacystin in cultured cells.

L R Dick et al.

The Journal of biological chemistry, 272(1), 182-188 (1997-01-03)

The natural product lactacystin exerts its cellular antiproliferative effects through a mechanism involving acylation and inhibition of the proteasome, a cytosolic proteinase complex that is an essential component of the ubiquitin-proteasome pathway for intracellular protein degradation. In vitro, lactacystin does

Activity dependent protein degradation is critical for the formation and stability of fear memory in the amygdala.

Timothy J Jarome et al.

PloS one, 6(9), e24349-e24349 (2011-10-01)

Protein degradation through the ubiquitin-proteasome system [UPS] plays a critical role in some forms of synaptic plasticity. However, its role in memory formation in the amygdala, a site critical for the formation of fear memories, currently remains unknown. Here we

Coordinated regulation of dendrite arborization by epigenetic factors CDYL and EZH2

Qi C, et al.

The Journal of Neuroscience, 34(13), 4494-4508 (2014)

Proteasome inhibition triggers activity-dependent increase in the size of the recycling vesicle pool in cultured hippocampal neurons.

Kristen Willeumier et al.

The Journal of neuroscience : the official journal of the Society for Neuroscience, 26(44), 11333-11341 (2006-11-03)

The ubiquitin proteasome system, generally known for its function in protein degradation, also appears to play an important role in regulating membrane trafficking. A role for the proteasome in regulating presynaptic release and vesicle trafficking has been proposed for invertebrates

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