Lactacystin

Names

[ Name ]:
Lactacystin

[Synonym ]:
L-Cysteine, N-acetyl-S-[[(3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-2-pyrrolidinyl]carbonyl]-
(+)-Lactacystin
MFCD01076525
N-Acetyl-S-({(2R,3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidin-2-yl}carbonyl)-L-cysteine
L-cysteine, S-[[(2R,3S,4R)-3,4-dihydro-3,5-dihydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-2H-pyrrol-2-yl]carbonyl]-N-(1-hydroxyethylidene)-, (E)-
L-Cysteine, N-acetyl-S-[[(2R,3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-2-pyrrolidinyl]carbonyl]-
LACTACYSTIN
N-Acetyl-S-({(3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-2-pyrrolidinyl}carbonyl)-L-cysteine
N-Acetyl-S-({(2R,3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-2-pyrrolidinyl}carbonyl)-L-cysteine

Biological Activity

[Description]:

Lactacystin, an antibiotic Streptomyces spp. metabolite, is a potent and selective proteasome inhibitor with an IC50 of 4.8 μM for 20S proteasome. Lactacystin also inhibits the lysosomal enzyme cathepsin A[1]. Lactacystin inhibits cell growth and induces neurite outgrowth[2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Proteasome

Research Areas >> Neurological Disease

[Target]

IC50: 4.8 μM (proteasome)[1]

[In Vivo]

Lactacystin (microinjection; 2 µg) induces a Parkinson’s disease-like motor phenotype 5-7 days after injection in young and adult mice[2]. Animal Model: Male C57Bl/6RccHsd mice with 8-9 weeks (young) and 12-14 months (adult) old[2] Dosage: 2 µg Administration: Microinjection Result: Induced a Parkinson’s disease-like motor phenotype 5-7 days after injection in young and adult mice.

[References]

[1]. Csizmadia V, et al. Effect of proteasome inhibitors with different chemical structures on the ubiquitin-proteasomesystem in vitro. Vet Pathol. 2010 Mar;47(2):358-67.

[2]. Savolainen MH, et al. Nigral injection of a proteasomal inhibitor, lactacystin, induces widespread glial cell activationand shows various phenotypes of Parkinson's disease in young and adult mouse. Exp Brain Res. 2017 Jul;235(7):2189-2202.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
714.9±60.0 °C at 760 mmHg

[ Melting Point ]:
233-235ºC dec.

[ Molecular Formula ]:
C₁₅H₂₄N₂O₇S

[ Molecular Weight ]:
376.425

[ Flash Point ]:
386.1±32.9 °C

[ Exact Mass ]:
376.130432

[ PSA ]:
178.33000

[ LogP ]:
-1.10

[ Vapour Pressure ]:
0.0±5.2 mmHg at 25°C

[ Index of Refraction ]:
1.560

[ Storage condition ]:
−20°C

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Articles

Neuroprotective effect of modified Chungsimyeolda-tang, a traditional Korean herbal formula, via autophagy induction in models of Parkinson's disease.

J. Ethnopharmacol. 159 , 93-101, (2014)

Previous studies in our laboratory revealed the neuroprotective effect of modified Yeoldahanso-tang (MYH) in models of Parkinson׳s disease (PD). In this study, we investigated another traditional Kore...

Septins arrange F-actin-containing fibers on the Chlamydia trachomatis inclusion and are required for normal release of the inclusion by extrusion.

MBio 5(5) , e01802-14, (2014)

Chlamydia trachomatis is an obligate intracellular human pathogen that grows inside a membranous, cytosolic vacuole termed an inclusion. Septins are a group of 13 GTP-binding proteins that assemble in...

Development of two novel high-throughput assays to quantify ubiquitylated proteins in cell lysates: application to screening of new anti-malarials.

Malaria Journal 14 , 200, (2015)

The ubiquitin proteasome system (UPS) is one of the main proteolytical pathways in eukaryotic cells and plays an essential role in key cellular processes such as cell cycle, stress response, signal tr...