ShikoninA naphthoquinone derivative with angiogenesis inhibitor properties

Shikonin (CAS 517-89-5)

Shikonin | CAS 517-89-5 is rated 5.0 out of 5 by 1.
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Application: A naphthoquinone derivative with angiogenesis inhibitor properties
CAS Number: 517-89-5
Purity: ≥98%
Molecular Weight: 288.3
Molecular Formula: C16H16O5
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Shikonin is a naturally occurring active chemical found in the root of Lithospermum erythrorhizon and used as a Chinese herb. The compound is a naphthoquinone derivative and has been shown to have anti-inflammatory and anti-tumor properties, as well as alter chemokine expression and function. Angiogenesis studies have shown that Shikonin can inhibit proliferation and migration of endothelial cells, block integrin αvβ3 expression, and inhibit B16 melanoma- and tumor necrosis factor-alpha-inuced angiogenesis in mice. Shikonin can down-regulate protein and mRNA expression of CKR-5 (CCR5), a primary HIV-1 coreceptor, in macrophages in HIV studies. Shikonin is an inhibitor of PKM2.


References

1. Wang, W.J., et al. 1994. Yao Xue Xue Bao. 29: 161-165. PMID: 8079645
2. Hisa, T., et al. 1998. Anticancer Res. 18: 783-790. PMID: 9615720
3. Chen, X., et al. 2003. Antimicrob. Agents Chemother. 47: 2810-2816. PMID: 12936978
4. Nigorikawa, K., et al. 2006. Mol. Pharmacol. 70: 1143-1149. PMID: 16804092
5. Kim, Y.O., et al. 2010. Korean J. Physiol. Pharmacol. 14: 199-204. PMID: 20827333

Physical State :
Solid
Solubility :
Soluble in DMSO (10 mg/ml).
Storage :
Store at 4° C
Melting Point :
202.18° C (Predicted)
Boiling Point :
~567.4° C at 760 mmHg (Predicted)
Density :
~1.4 g/cm3 (Predicted)
Refractive Index :
n20D 1.64 (Predicted)
IC50 :
HCT-116: IC50 = 230 nM (human); HL-60 : IC50 = 440 nM (human); HepG2 : IC50 = 240 nM (human); K562/ADR cells : IC50 = 670 nM (human); TPEN: IC50 = 2.7 µM
pK Values :
pKa: 7.34 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
RTECS :
QL8000200
Transport :
UN 3077, Class 9, Packing group III
PubChem CID :
479503
SMILES :
CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C

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Shikonin  Product Citations

See how others have used Shikonin. Click on the entry to view the PubMed entry .

Citations 1 to 5 of 5 total

PMID: # 29925224  Han, X.|Kang, KA.|Piao, MJ.|Zhen, AX.|Hyun, YJ.|Kim, HM.|Ryu, YS.|Hyun, JW.| et al. 2019. Biomol Ther (Seoul). 27: 41-47.

PMID: # 27223482  Gupta, B. et al. 2016. Can. J. Physiol. Pharmacol. 94: 788-96.

PMID: # 24248858  Wang, L. et al. 2014. Neurochemical research. 39: 97-106.

PMID: # 20827333  Kim, YO. et al. 2010. Korean J. Physiol. Pharmacol. 14: 199-204.

PMID: # 11704659  Tomoda, K. et al. 2002. J. Biol. Chem. 277: 2302-10.

Citations 1 to 5 of 5 total
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Rated 5 out of 5 by from Bettaieb Bettaieb, A. et al. (PubMed 26374090) found that Shikonin, a naphthoquinone derivative with angiogenesis inhibitor properties, treated mice fed regular chow, exhibited improved glucose tolerance compared to cotnrols. In addition, Shikonin treated mice fed a high-fat diet displayed decreased weight gain and resistance to high-fat diet-induced glucose intolerance. -SCBT Publication Review
Date published: 2015-03-15
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