Shikonin

Catalog No.S8279 Batch:S827901

Technical Data

Formula	C₁₆H₁₆O₅
Molecular Weight	288.30	CAS No.	54952-43-1
Solubility (25°C)*	In vitro	DMSO	57 mg/mL (197.71 mM)
		Ethanol	23 mg/mL (79.77 mM)
		Water	Insoluble
* <1 mg/ml means slightly soluble or insoluble. * Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations. * Room temperature shipping (Stability testing shows this product can be shipped without any cooling measures.)

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Biological Activity

Description

Shikonin, a potent and specific Pyruvate kinase M2 (PKM2) inhibitor, is a major component of zicao (purple gromwell, the dried root of Lithospermum erythrorhizon), a Chinese herbal medicine with various biological activities. It is also an inhibitor of TMEM16A chloride channel activity using cell-based fluorescent-quenching assay. Shikonin exerts an anti-inflammatory effect by inhibiting tumor necrosis factor-α (TNF-α) and prevents activation of nuclear factor-κB (NF-κB) pathway via proteasome inhibition.

Targets

chemokine receptor ^[1]	TNF-α ^[4]	Proteasome ^[4]	NF-κB ^[1]	PKM2 ^[3] (FBP absence)	View More
				0.3 μM	View More

In vitro

At nanomolar concentrations, shikonin inhibits monocyte chemotaxis and calcium flux in response to a variety of CC chemokines (CCL2 [monocyte chemoattractant protein 1], CCL3 [macrophage inflammatory protein 1α], and CCL5 [regulated upon activation, normal T-cell expressed and secreted protein]), the CXC chemokine (CXCL12 [stromal cell-derived factor 1α]), and classic chemoattractants (formylmethionyl-leucine-phenylalanine and complement fraction C5a). Shikonin down-regulates surface expression of CCR5, a primary HIV-1 coreceptor, on macrophages. The anti-HIV and anti-inflammatory activities of shikonin may be related to its interference with chemokine receptor expression and function^[1]. Shikonin inhibits enterocyte calcium-activated chloride channels, the inhibitory effect is partially through inhibition of basolateral K+ channel activity^[2].

In vivo

Shikonin significantly delays intestinal motility in mice and reduces stool water content in a neonatal mice model of rotaviral diarrhea without affecting the viral infection process in vivo. Shikonin has been reported to have antioxidant, antibacterial, antiparasitic, antiviral and wound-healing activities. Shikonin inhibits allergic action as well as tracheal hyperresponsiveness in vivo. Intraperitonal injection of shikonin has been demonstrated to result in some toxicity, with an LD50 of 20 mg/kg. Shikonin absorption is fast if given by oral gavage and muscle injection, as it is barely detected in the plasma after 1 min, with a oral gavage yielding a bioavailability of about 34%^[2].

Protocol (from reference)

Cell Assay:^{^[1]}	Cell lines Human monocytes Concentrations 10, 1, 0.1, 0.01 μM Incubation Time 12 and 24 hours Method Freshly isolated human monocytes are plated in a 96-microwell plate (Costar) at 10⁵ cells per well with shikonin at a final concentration of 10, 1, 0.1, 0.01 μM. The numbers of viable cells, as detected by MTS test and the trypan blue exclusion assay, were measured 12 and 24 h after incubation at 37°C in humidified air with 5% CO2.
Animal Study:^{^[2]}	Animal Models Neonatal ICR mice Dosages 0.4 and 1.7 μg in 30 μL PBS Administration oral administration

Cell Assay:^{^[1]}

Cell lines
Human monocytes
Concentrations
10, 1, 0.1, 0.01 μM
Incubation Time
12 and 24 hours
Method
Freshly isolated human monocytes are plated in a 96-microwell plate (Costar) at 10⁵ cells per well with shikonin at a final concentration of 10, 1, 0.1, 0.01 μM. The numbers of viable cells, as detected by MTS test and the trypan blue exclusion assay, were measured 12 and 24 h after incubation at 37°C in humidified air with 5% CO2.

Animal Study:^{^[2]}

Animal Models
Neonatal ICR mice
Dosages
0.4 and 1.7 μg in 30 μL PBS
Administration
oral administration

References

[4] Yan Yan, et al. Chin Med J (Engl) . 2015 Aug 20;128(16):2228-33.

+ Expand

Selleck's Shikonin has been cited by 33 publications

PKM2-mediated neuronal hyperglycolysis enhances the risk of Parkinson's disease in diabetic rats [ J Pharm Anal, 2023, 13(2):187-200]	PubMed: 36908857
Shikonin reverses pyruvate kinase isoform M2-mediated propranolol resistance in infantile hemangioma through reactive oxygen species-induced autophagic dysfunction [ Cancer Sci, 2023, 114(3):806-821]	PubMed: 36369903
Metabolic Reprogramming by Ribitol Expands the Therapeutic Window of BETi JQ1 against Breast Cancer [ Cancers (Basel), 2023, 15(17)4356]	PubMed: 37686632
Metabolic Reprogramming by Ribitol Expands the Therapeutic Window of BETi JQ1 against Breast Cancer [ Cancers (Basel), 2023, 15(17)4356]	PubMed: 37686632
Shikonin improves pulmonary vascular remodeling in monocrotaline‑induced pulmonary arterial hypertension via regulation of PKM2 [ Mol Med Rep, 2023, 27(3)60]	PubMed: 36734266
Celastrol mitigates inflammation in sepsis by inhibiting the PKM2-dependent Warburg effect [ Mil Med Res, 2022, 9(1):22]	PubMed: 35596191
Pyruvate Facilitates FACT-Mediated γH2AX Loading to Chromatin and Promotes the Radiation Resistance of Glioblastoma [ Adv Sci (Weinh), 2022, 10.1002/advs.202104055]	PubMed: 35048565
Systematic identification of biomarker-driven drug combinations to overcome resistance [ Nat Chem Biol, 2022, 10.1038/s41589-022-00996-7]	PubMed: 35332332
Integrin β3-PKM2 pathway-mediated aerobic glycolysis contributes to mechanical ventilation-induced pulmonary fibrosis [ Theranostics, 2022, 12(14):6057-6068]	PubMed: 36168620
Capsaicin ameliorates inflammation in a TRPV1-independent mechanism by inhibiting PKM2-LDHA-mediated Warburg effect in sepsis [ Cell Chem Biol, 2022, S2451-9456(22)00243-4]	PubMed: 35858615

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