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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)
Biological Activity for (R)-Shikonin
(R)-Shikonin is a 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. (R)-Shikonin suppresses glycolysis in cancer cells by inhibiting tumor-specific pyruvate kinase M2 (PKM2) (IC50 = 0.3 μM) and inhibits tumor proliferation. Induces necroptosis in MCF-7 and HEK293 cancer cell lines. (R)-Shikonin also displays anti-inflammatory activity in a mouse model of collagen-induced arthritis.
Technical Data for (R)-Shikonin
| 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.
Product Datasheets for (R)-Shikonin
References for (R)-Shikonin
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
Zhao et al (2018) Shikonin inhibits tumor growth in mice by suppressing pyruvate kinase M2-mediated aerobic glycolysis. Sci.Rep. 8 14517 PMID: 30266938
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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, Other, Kinases, Necroptosis, HIV, 6829, Tocris Bioscience
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