565850

Shikonin

≥98% (HPLC), solid, Pyruvate kinase inhibitor, Calbiochem^®

• Synonym(s): Shikonin, Pyruvate Kinase Inhibitor II
• Empirical Formula (Hill Notation): C₁₆H₁₆O₅
• CAS Number: 517-89-5
• Molecular Weight: 288.30
• MDL number: MFCD00075680
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Product Name: Shikonin, A naphthoquinone found in the Chinese herb Shiunko.
• Quality Level: 100
• description: RTECS - QL8000200
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: red
• solubility: DMSO: 10 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: OC(CC=C(C)C)C1=CC(=O)c2c(c(ccc2O)O)C1=O
• InChI: 1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3
• InChI key: NEZONWMXZKDMKF-UHFFFAOYSA-N

Description

General description

A naphthoquinone found in the Chinese herb Lithospermum erythrorhizon. Possesses significant antibacterial, anti-inflammatory and antitumor activities. Inhibits TNF-α and B-16 melanoma-induced angiogenesis in mice. Blocks the expression of integrin αVβ3 and inhibits endothelial cells proliferation and migration in vitro. Also induces apoptosis in HL60 human promyelocytic leukemia cell line. Selectively blocks PKM2 (IC₅₀<1 µM) over PKM1 and PKL activities (IC₅₀ in the range of 10-20 µM), and inhibits cancer cell glycolysis.

Biochem/physiol Actions

Cell permeable: no

Primary Target
TNF-α-induced and B-16 melanoma-induced angiogenesis

Product does not compete with ATP.

Reversible: no

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Chen, J., et al. 2011. Oncogene30, 4297.
Li, H., et al. 1999. Phytother. Res.13, 236.
Yoon, Y., et al. 1999. Planta Med.65, 532.
Hisa, T., et al. 1998. Anticancer Res. 18, 783.

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable