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565850

Sigma-Aldrich

Shikonin

A naphthoquinone found in the Chinese herb Shiunko.

Synonym(s):

Shikonin, Pyruvate Kinase Inhibitor II

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About This Item

Empirical Formula (Hill Notation):
C16H16O5
CAS Number:
517-89-5
Molecular Weight:
288.30
MDL number:
MFCD00075680
UNSPSC Code:
12352200

Quality Level

100

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

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

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.
A naphthoquinone found in the Chinese herb Shiunko. Possesses significant antibacterial, anti-inflammatory, and antitumor activities. Inhibits TNF-α-induced and B-16 melanoma-induced angiogenesis in mice. Blocks the expression of integrin αvβ3 and inhibits endothelial cell proliferation and migration in vitro. Also induces apoptosis in HL60 human promyelocytic leukemia cell line.

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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