426100

Lactacystin

≥99% (HPLC), solid, proteasome inhibitor, Calbiochem^®

• Synonym(s): Lactacystin, Synthetic, Proteasome Inhibitor VI
• Empirical Formula (Hill Notation): C₁₅H₂₄N₂O₇S
• CAS Number: 1258004-00-0
• Molecular Weight: 376.43
• MDL number: MFCD01076525
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥99% (HPLC)
• Form: solid
• Storage condition: OK to freeze

Properties

• Product Name: Lactacystin, Synthetic, Lactacystin, Synthetic, CAS 1258004-00-0, is an irreversible inhibitor of 20S proteasome inhibitor (IC₅₀ = 500 nM). A covalent inhibitor of the chymotrypsin & trypsin-like activities of proteasome.
• Quality Segment: 100
• assay: ≥99% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white
• solubility: DMSO: 50 mg/mL, water: soluble
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: S(C[C@H](NC(=O)C)C(=O)O)C(=O)[C@]1(NC(=O)[C@@H]([C@@H]1O)C)[C@@H](O)C(C)C
• 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-AFGIITKNSA-N

Description

General description

An irreversible proteasome inhibitor. A Streptomyces metabolite that acts as a highly specific inhibitor of the 20S proteasome (MCP; multicatalytic proteinase complex) (IC₅₀ = 500 nM for 20S proteasome). Blocks proteasome activity by targeting the catalytic β-subunit. Acts as a covalent inhibitor of the chymotrypsin- and trypsin-like activities of the proteasome. Induces neurite outgrowth in Neuro 2A mouse neuroblastoma cells and inhibits progression of synchronized Neuro 2A cells and MG-63 human osteosarcoma cells beyond the G₁ phase of the cell cycle. Reported to induce apoptosis in human monoblast U937 cells. Also inhibits NF-κB activation (IC₅₀ = 10 µM).

Biochem/physiol Actions

Cell permeable: no

Primary Target
20S proteasome (MCP; multicatalytic proteinase complex)

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 500 nM against 20S proteasome; 10 µM against NF-κB activation

Preparation Note

Following reconstitution in DMSO, aliquot and freeze (-20°C). DMSO stock solutions are stable for up to 1 month at -20°C. Unstable in aqueous solutions; reconstitute in H₂O just prior to use.

Other Notes

Keyomarsi, K., et al. 2011. Cell. Biol. Toxicol.27, 123.
Adams, J., and Stein, R. 1996. Ann. Rep. Med. Chem.31, 279.
Dick, L.R., et al. 1996. J. Biol. Chem.271, 7273.
Oda, K., et al. 1996. Biochem. Biophys. Res.Commun.219, 800.
Fenteany, G., et al. 1995. Science268, 726.
Imajoh-Ohmi, S., et al. 1995. Biochem.Biophys. Res. Commun.217, 1070.
Jensen, T.J., et al. 1995. Cell 83, 129.
Katagiri, M.M., et al. 1995. J. Antibiot.48, 344.
Mori, S., et al. 1995. J. Biol. Chem.270, 29447.
Tanaka, H., et al. 1995. Biochem. Biophys. Res. Commun.216, 291.
Fenteany, G., et al. 1994. Proc. Natl. Acad.Sci. USA91, 3358.
Omura, S., et al. 1991. J. Antibiot.44, 117.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable