Product overview

Name Lactacystin
Purity >98%
Description Potent, selective, irreversible proteasome inhibitor
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Biological Data

Biological description Potent, selective, cell-permeable and irreversible proteasome inhibitor. Thought to irreversibly bind the active site N-terminal threonine residue of the 20S proteasome catalytic β-subunit to inhibit chymotrypsin and trypsin-like activities and block proteasome activity. Shows anticancer and anti-adipogenic activity, induces neuritogenesis, apoptosis and autophagy. Also inhibits NF-κB activation

Solubility & Handling

Storage instructions +4°C
Solubility overview Soluble in water, and in DMSO
Important This product is for RESEARCH USE ONLY and is not intended for therapeutic or diagnostic use. Not for human or veterinary use.

Calculators

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Chemical Data

Purity >98%
Chemical name (2R,3S,4R)-3-Hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxo-2-pyrrolidinecarboxy-N-acetyl-L-cysteine thioester
Molecular Weight 376.4
Chemical structure Lactacystin [133343-34-7] Chemical Structure
Molecular Formula C15H24N2O7S
CAS Number 133343-34-7
PubChem identifier 6610292
SMILES O=C1N[C@]([C@@](SC[C@H](NC(C)=O)[C@](O)=O)=O)([C@H](C(C)C)O)[C@@H](O)[C@H]1C
Source Streptomyces lactacystinnaeus
InChi 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
InChiKey DAQAKHDKYAWHCG-MJZHQVMOSA-N
MDL number MFCD01076525
Appearance White to off-white solid

References for Lactacystin

References are publications that support the biological activity of the product
  • Lactacystin: first-in-class proteasome inhibitor still excelling and an exemplar for future antibiotic research

    Omura and Crump (2019) J Antbiot (Tokyo) 72(4) : 189-201.
  • Inhibition of proteasome activities and subunit-specific amino-terminal threonine modification by lactacystin

    Fenteany et al (1995) Science 268(5211) : 726-31.
  • Lactacystin, a novel microbial metabolite, induces neuritogenesis of neuroblastoma cells

    Omura et al (1991) J Antbiot (Tokyo) 44(1) : 113-6.

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