LACTACYSTIN

ChemicalBook > CAS DataBase List > LACTACYSTIN

Product Name: LACTACYSTIN
CAS No.: 133343-34-7
Chemical Name: LACTACYSTIN
Synonyms: Lacta;Aids008388;LACTACYSTIN;Aids-008388;(+)-LACTACYSTIN;LACTACYSTIN (NATIVE);LACTACYSTIN USP/EP/BP;LACTACYSTIN, SYNTHETIC;LACTACYSTIN, STREPTOMYCES SP;Lactacystin, proteasome inhibitor
CBNumber: CB5136696
Molecular Formula: C15H24N2O7S
Formula Weight: 376.43
MOL File: 133343-34-7.mol

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LACTACYSTIN Property

Melting point:: 233-235°C dec.
Boiling point:: 714.9±60.0 °C(Predicted)
Density: 1.367±0.06 g/cm3(Predicted)
storage temp.: -20°C
solubility: Soluble in DMSO (up to 20 mg/ml), in Water (up to 10 mg/ml), or in Ethanol (up to 1 mg/ml).
pka: 3.11±0.10(Predicted)
form: powder
color: White to off-white
Water Solubility: Soluble to 10 mM in water
Stability:: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month. Solutions in water are not stable and must be used with one working day. Aqueous solutions should not be stored.

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: L6785
Product name: Lactacystin
Purity: ≥90% (HPLC)
Packaging: 0.2mg
Price: $462
Updated: 2024/03/01

Cayman Chemical

Product number: 70980
Product name: Lactacystin
Purity: ≥98%
Packaging: 50μg
Price: $44
Updated: 2024/03/01

Cayman Chemical

Product number: 70980
Product name: Lactacystin
Purity: ≥98%
Packaging: 100μg
Price: $75
Updated: 2024/03/01

Cayman Chemical

Product number: 70980
Product name: Lactacystin
Purity: ≥98%
Packaging: 500μg
Price: $308
Updated: 2024/03/01

Cayman Chemical

Product number: 70980
Product name: Lactacystin
Purity: ≥98%
Packaging: 1mg
Price: $570
Updated: 2024/03/01

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LACTACYSTIN Chemical Properties,Usage,Production

Description

Lactacystin is a microbial metabolite isolated from Streptomyces that is now widely used as a selective inhibitor of the 20S proteasome. Lactacystin was first characterized by its ability to induce differentiation and inhibit cell cycle progression in several tumor cell lines. At concentrations from 2 to 10 μM, lactacystin induces the outgrowth of neurites in the neuroblastoma cell line Neuro2a. Lactacystin irreversibly alkylates subunit X of the 20S proteasome. The concomitant inhibition of proteasome peptidase activity results in the accumulation of a variety of ubiquitinated proteins which would normally undergo rapid degradation. Thus, the effects of lactacystin are pleiotropic and depend substantially on the expression pattern of signalling proteins within the treated cell.

Chemical Properties

White Powder

Uses

A selective and potent inhibitor of proteasome-mediated degradation of ubiquitin-tagged proteins. A Streptomyces metabolite that acts as a highly specific inhibitor of the 20S proteasome (MCP: multicatalytic proteinase complex)

Uses

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

Definition

ChEBI: L-Cysteine substituted at nitrogen by an acetyl group and at sulfur by a substituted-lactam carbonyl group.

General Description

Lactacystin is an antibiotic?and a metabolite of Streptomyces?spp.

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.

target

GABA Receptor | HDAC | NF-kB | p65 | Caspase

storage

+4°C

References

1) Omura et al. (1991), Lactacystin, a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells; J. Antibiot., 44 113 2) Fenteany et al. (1995), Inhibition of proteasome activities and subunit-specific amino-terminal threonine modification by lactacystin; Science, 268 726

LACTACYSTIN Preparation Products And Raw materials

Raw materials

Preparation Products

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LACTACYSTIN Suppliers

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View Lastest Price from LACTACYSTIN manufacturers

Career Henan Chemical Co

Product: lactacystin 133343-34-7
Price: US $1.00/g
Min. Order: 1g
Purity: 95-99%
Supply Ability: 1ton
Release date: 2020-01-10

133343-34-7, LACTACYSTINRelated Search:

CLASTO-LACTACYSTIN,Clasto-lactacystin -Lactone, Omuralide,Clasto-lactacystin b-Lactone, Omuralide,CLASTO-LACTACYSTIN B-LACTONE MG-132 (+)-LACTACYSTIN ALLYL ESTER,LACTACYSTIN ALLYL ESTER MG-115 N-PROPYL 3-MERCAPTOPROPIONATE 3,3'-THIODIPROPANOL S-Butyl-D-cysteine dacisteine (S)-4-Hydroxy-2-pyrrolidinone Fudosteine S-Methyl 2-methylthiobutyrate LACTACYSTIN L-Cysteine N-ACETYL-S-(3-HYDROXYPROPYL)CYSTEINE 5,5-Dimethyl-2-pyrrolidinone clasto-lactacystin β-lactone,LACTACYSTIN, CLASTO-, BETA-LACTONE,CLASTO-LACTACYSTIN BETA-LACTONE S-METHYL 4-METHYLPENTANETHIOATE 5-HYDROXYMETHYL-3-METHYLPYRROLIDIN-2-ONE

(2R,3S,4R)-3-HYDROXY-2-[(1S)-1-HYDROXY-2-METHYLPROPYL]-4-METHYL-5-OXO-2-PYRROLIDINECARBOXY-N-ACETYL-L-CYSTEINE THIOESTER

3S-HYDROXY-2R-(1-HYDROXY-2-METHYLPROPYL)-4R-METHYL-5-OXO-2-PYRROLIDINECARBOXYLATE-N-ACETYL-L-CYSTEINE

(+)-LACTACYSTIN

LACTACYSTIN

LACTACYSTIN (NATIVE)

LACTACYSTIN, STREPTOMYCES SP

LACTACYSTIN, SYNTHETIC

N-ACETYL-S-[(2R,3S,4R)-3-HYDROXY-2-[(1S)-1-HYDROXY-2-METHYLPROPYL]-4-METHYL-5-OXO-2-PYRROLIDINECARBONYL]-L-CYSTEINE

(2R)-2-(Acetylamino)-3-[[(2R)-3β-hydroxy-4β-methyl-2-[(S)-1-hydroxy-2-methylpropyl]-5-oxopyrrolidine-2-yl]carbonylthio]propanoic acid

(2R)-2-(Acetylamino)-3-[[[(2R,3S,4R)-2-[(1S)-2-methyl-1-hydroxypropyl]-3-hydroxy-4-methyl-5-oxopyrrolidin-2-yl]carbonyl]thio]propionic acid

S-[2R,3S,4R]-3-HYDROXY-2-[(1S)-1-HYDROXY-2-METHYLPROPYL]-4-METHYL-5-OXO-2-PYROLIDINECARBONYL

Aids008388

Aids-008388

L-Cysteine, N-acetyl-, (2R,3S,4R)-3-hydroxy-2-(1-hydroxy-2-methylpropyl)-4-methyl-5-oxo-2-pyrrolidinecarboxylate (ester)

N-Acetyl-S-[(3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-Methylpropyl]-4-Methyl-5-oxo-D-prolyl]-L-cysteine

L-Cysteine, N-acetyl-S-[(3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-D-prolyl]-

LACTACYSTIN USP/EP/BP

Lacta

Lactacystin, proteasome inhibitor

133343-34-7

C15H24N2O7S

Biochemicals and Reagents

BioChemical

Enzyme Inhibitors

Enzyme Inhibitors by Enzyme

Enzymes, Inhibitors, and Substrates

Proteasome inhibitor

P to Q

All Inhibitors

Inhibitors

Metabolites

Calpain and Proteasome InhibitorsProteasome, Calpain and Lysosomal Proteases

InhibitorsProtease Inhibitors

Intracellular Protein Degradation

Nitric Oxide and Cell Stress

P to

Protease Inhibitor Specificity Index

Proteasome inhibitor

Proteasome inhibitorEnzyme Inhibitors by Enzyme

Proteasomes

Protease

ProteaseInhibitors