(R)-Shikonin

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Cat.No. 6829 - (R)-Shikonin | C16H16O5 | CAS No. 517-89-5
Description: PTEN inhibitor; induces necroptosis; anti-inflammatory
Chemical Name: 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthalenedione
Purity: ≥98% (HPLC)
Datasheet
Citations
Reviews
Literature (1)

Biological Activity

PTEN and inflammasome inhibitor. Inhibits PTEN's phosphatase activity (IC50 = 2.7 µM) and NLRP3 activation. Also blocks TNF-α and NF-κB signaling. Attenuates HIV-1 replication at nanomolar concentrations. Suppresses glycolysis in cancer cells by inhibiting tumor-specific pyruvate kinase M2 (PKM2) (IC50 = 0.3 μM). Induces necroptosis in MCF-7 and HEK293 cancer cell lines. Displays anti-inflammatory activity in a mouse model of collagen-induced arthritis.

Technical Data

M. Wt 288.3
Formula C16H16O5
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 517-89-5
PubChem ID 479503
InChI Key NEZONWMXZKDMKF-SNVBAGLBSA-N
Smiles C/C(C)=C\C[C@H](C1=CC(C2=C(C=CC(O)=C2C1=O)O)=O)O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 28.83 100
ethanol 5.77 20

Preparing Stock Solutions

The following data is based on the product molecular weight 288.3. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3.47 mL 17.34 mL 34.69 mL
5 mM 0.69 mL 3.47 mL 6.94 mL
10 mM 0.35 mL 1.73 mL 3.47 mL
50 mM 0.07 mL 0.35 mL 0.69 mL

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References

References are publications that support the biological activity of the product.

McLoughlin et al (2018) The therapeutic potential of PTEN modulation: targeting strategies from gene to protein. Cell Chem.Biol. 25 19 PMID: 29153852

Nigorikawa et al (2006) A naphthoquinone derivative, shikonin, has insulin-like actions by inhibiting both phosphatase and tensin homolog deleted on chromosome 10 and tyrosine phosphatases. Mol.Pharmacol. 70 1143 PMID: 16804092

Hafner-Bratkovic et al (2018) NLRP3 lacking the leucine-rich repeat domain can be fully activated via the canonical inflammasome pathway. Nat.Commun. 9 5182 PMID: 30518920

Chen et al (2011) Shikonin and its analogs inhibit cancer cell glycolysis by targeting tumor pyruvate kinase-M2. Oncogene 30 4297 PMID: 21516121

Han et al (2007) Shikonin circumvents cancer drug resistance by induction of a necroptotic death. Mol. Cancer Ther. 6 1641 PMID: 17513612

Chen et al (2003) Shikonin, a Component of Chinese Herbal Medicine, Inhibits Chemokine Receptor Function and Suppresses Human Immunodeficiency Virus Type 1 Antimicrob. Agents Chemother. 47 2810 PMID: 12936978

Kim et al (2010) The efficacy of shikonin on cartilage protection in a mouse model of rheumatoid arthritis. Korean J.Physiol.Pharmacol. 14 199 PMID: 20827333


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Keywords: (R)-Shikonin, (R)-Shikonin supplier, PTEN, inhibitors, inhibits, inducers, necroptosis, anti-inflammatory, NLRP3, TNF-α, NF-κB, HIV-1, replication, pyruvate, kinase, M2, PKM2, NF-kappaB, TNF-alpha, alfa, Protein, Tyrosine, Phosphatases, Inflammasomes, NF-kB/IkB, Cytokines, Antivirals, Other, Kinases, Necroptosis, 6829, Tocris Bioscience

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Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis