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MedKoo Cat#: 561250 | Name: Shikonin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Shikonin is a natural product from the root of Lithospermum erythrorhizon and a specific inhibitor of pyruvate kinase M2 (PKM2). Shikonin also suppresses the ATF2 pathway in skin carcinogenesis. Shikonin has potent antidiabetic activity by inhibiting the action of the aldose reductase (AR) enzyme and the protein-tyrosine phosphatase 1B (PTP1B).

Chemical Structure

Shikonin
Shikonin
CAS#517-89-5

Theoretical Analysis

MedKoo Cat#: 561250

Name: Shikonin

CAS#: 517-89-5

Chemical Formula: C16H16O5

Exact Mass: 288.0998

Molecular Weight: 288.30

Elemental Analysis: C, 66.66; H, 5.59; O, 27.75

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 Weeks
50mg USD 600.00 2 Weeks
100mg USD 950.00 2 Weeks
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Related CAS #
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Synonym
Shikonin; Tokyo Violet
IUPAC/Chemical Name
5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
InChi Key
NEZONWMXZKDMKF-SNVBAGLBSA-N
InChi Code
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/t10-/m1/s1
SMILES Code
O=C1C([C@H](O)C/C=C(C)/C)=CC(C2=C1C(O)=CC=C2O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Shikonin is a potent TMEM16A chloride channel inhibitor with an IC50 of 6.5 μM. Shikonin is a specific PKM2 inhibitor and can inhibit TNF-α and NF-κB pathway. Shikonin decreases exosome secretion through the inhibition of glycolysis. Shikonin inhibits AIM2 inflammasome activation.
In vitro activity:
Shikonin has potential for melanoma treatment, as it causes non-apoptotic cell death in B16F10 melanoma cells. There was a large decrease in cellular growth and proliferation with increasing shikonin concentrations. MTT assays suggested that necroptosis, autophagy, and reactive oxygen species are a part of shikonin's mechanism of action. Western blotting confirmed that shikonin-treated melanoma cells had increased levels of stress-related proteins, such as CHOP, RIP, pRIP. Reference: Anticancer Agents Med Chem. 2023;23(16):1880-1887. https://pubmed.ncbi.nlm.nih.gov/37393553/
In vivo activity:
In a murine model of heat stroke, shikonin demonstrated anti-inflammatory and antioxidative characteristics by reducing the production of IL-17A and inhibiting its expression. SK delayed the rising rate of core temperature, prolonged the survival time of mice, and improved organ injury and coagulation function markedly. Serum HS biomarkers were decreased significantly by SK, which contribute to liver and lung protection in the models. Reference: Biomed Pharmacother. 2023 Oct;166:115346. https://pubmed.ncbi.nlm.nih.gov/37643485/
Solvent mg/mL mM comments
Solubility
DMSO 125.0 433.58
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 288.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Ahmad H, Crotts MS, Jacobs JC, Baer RW, Cox JL. Shikonin Causes Non-apoptotic Cell Death in B16F10 Melanoma. Anticancer Agents Med Chem. 2023;23(16):1880-1887. doi: 10.2174/1871520623666230701000338. PMID: 37393553. 2. Chen Q, Han H, Lin F, Yang L, Feng L, Lai X, Wen Z, Yang M, Wang C, Ma Y, Yin T, Lu G, Lin H, Qi J, Yang Y. Novel shikonin derivatives suppress cell proliferation, migration and induce apoptosis in human triple-negative breast cancer cells via regulating PDK1/PDHC axis. Life Sci. 2022 Dec 1;310:121077. doi: 10.1016/j.lfs.2022.121077. Epub 2022 Oct 13. PMID: 36244412. 3. Luo Q, Ji XY, Zhang L, Huang X, Wang XQ, Zhang B. Shikonin prevents mice from heat stroke-induced death via suppressing a trigger IL-17A on the inflammatory and oxidative pathways. Biomed Pharmacother. 2023 Oct;166:115346. doi: 10.1016/j.biopha.2023.115346. Epub 2023 Aug 27. PMID: 37643485. 4. He Y, Luo K, Hu X, Liu J, Hao M, Li Y, Xia X, Lü X, Shi C. Antibacterial Mechanism of Shikonin Against Vibrio vulnificus and Its Healing Potential on Infected Mice with Full-Thickness Excised Skin. Foodborne Pathog Dis. 2023 Feb;20(2):67-79. doi: 10.1089/fpd.2022.0065. PMID: 36779943.
In vitro protocol:
1. Ahmad H, Crotts MS, Jacobs JC, Baer RW, Cox JL. Shikonin Causes Non-apoptotic Cell Death in B16F10 Melanoma. Anticancer Agents Med Chem. 2023;23(16):1880-1887. doi: 10.2174/1871520623666230701000338. PMID: 37393553. 2. Chen Q, Han H, Lin F, Yang L, Feng L, Lai X, Wen Z, Yang M, Wang C, Ma Y, Yin T, Lu G, Lin H, Qi J, Yang Y. Novel shikonin derivatives suppress cell proliferation, migration and induce apoptosis in human triple-negative breast cancer cells via regulating PDK1/PDHC axis. Life Sci. 2022 Dec 1;310:121077. doi: 10.1016/j.lfs.2022.121077. Epub 2022 Oct 13. PMID: 36244412.
In vivo protocol:
1. Luo Q, Ji XY, Zhang L, Huang X, Wang XQ, Zhang B. Shikonin prevents mice from heat stroke-induced death via suppressing a trigger IL-17A on the inflammatory and oxidative pathways. Biomed Pharmacother. 2023 Oct;166:115346. doi: 10.1016/j.biopha.2023.115346. Epub 2023 Aug 27. PMID: 37643485. 2. He Y, Luo K, Hu X, Liu J, Hao M, Li Y, Xia X, Lü X, Shi C. Antibacterial Mechanism of Shikonin Against Vibrio vulnificus and Its Healing Potential on Infected Mice with Full-Thickness Excised Skin. Foodborne Pathog Dis. 2023 Feb;20(2):67-79. doi: 10.1089/fpd.2022.0065. PMID: 36779943.
1: Alherz FA, Saleh A, Alsheikh MY, Borg HM, Kabel AM, Abd Elmaaboud MA. Shikonin mitigates cyclophosphamide-induced cardiotoxicity in mice: the role of sirtuin-1, NLRP3 inflammasome, autophagy, and apoptosis. J Pharm Pharmacol. 2024 Sep 8:rgae119. doi: 10.1093/jpp/rgae119. Epub ahead of print. PMID: 39245439. 2: Yen JH, Keak PY, Wu CL, Chen HJ, Gao WY, Liou JW, Chen YR, Lin LI, Chen PY. Shikonin, a natural naphthoquinone phytochemical, exerts anti-leukemia effects in human CBF-AML cell lines and zebrafish xenograft models. Biomed Pharmacother. 2024 Oct;179:117395. doi: 10.1016/j.biopha.2024.117395. Epub 2024 Sep 5. PMID: 39241566. 3: Saeed M, Shoaib A, Tasleem M, Al-Shammary A, Kausar MA, El Asmar Z, Abdelgadir A, Sulieman AME, Ahmed EH, Zahin M, Ansari IA. Role of Alkannin in the Therapeutic Targeting of Protein-Tyrosine Phosphatase 1B and Aldose Reductase in Type 2 Diabetes: An In Silico and In Vitro Evaluation. ACS Omega. 2024 Aug 18;9(34):36099-36113. doi: 10.1021/acsomega.4c00082. PMID: 39220541; PMCID: PMC11359625. 4: Zhu H, Zhang H, Zhao XJ, Zhang L, Liu X, Zhang ZY, Ren YZ, Feng Y. Tetramerization of PKM2 Alleviates Traumatic Brain Injury by Ameliorating Mitochondrial Damage in Microglia. J Neuroimmune Pharmacol. 2024 Aug 28;19(1):48. doi: 10.1007/s11481-024-10138-6. PMID: 39196455. 5: Liu W, Zhao Y, Liu Q, Wu D, Li W, Fu Z, Yang L, Liang Y. Systematic bioinformatics analysis reveals the role of shikonin in blocking colon cancer progression by identifying senescence-induced genes. Front Pharmacol. 2024 Aug 12;15:1360587. doi: 10.3389/fphar.2024.1360587. PMID: 39188951; PMCID: PMC11345165. 6: Zeng F, Lai Y, Huang Y, Zhu F, Gao J, Chen Z, Zeng L, Feng M, Qiu P, Yuan S, Deng G. Shikonin from lithospermum erythrorhizon induces pyroptosis in trophoblast cells by activating the CTSB-NLRP3 inflammasome. Ann Med. 2024 Dec;56(1):2394584. doi: 10.1080/07853890.2024.2394584. Epub 2024 Aug 25. PMID: 39183455; PMCID: PMC11348813. 7: Shilnikova K, Kang KA, Piao MJ, Herath HMUL, Fernando PDSM, Boo HJ, Yoon SP, Hyun JW. Shikonin protects skin cells against oxidative stress and cellular dysfunction induced by fine particulate matter. Cell Biol Int. 2024 Aug 21. doi: 10.1002/cbin.12233. Epub ahead of print. PMID: 39169545. 8: Lian B, Zhang J, Yin X, Wang J, Li L, Ju Q, Wang Y, Jiang Y, Liu X, Chen Y, Tang X, Sun C. SIRT1 improves lactate homeostasis in the brain to alleviate parkinsonism via deacetylation and inhibition of PKM2. Cell Rep Med. 2024 Aug 20;5(8):101684. doi: 10.1016/j.xcrm.2024.101684. Epub 2024 Aug 10. PMID: 39128469; PMCID: PMC11384727. 9: Qi K, Li J, Hu Y, Qiao Y, Mu Y. Research progress in mechanism of anticancer action of shikonin targeting reactive oxygen species. Front Pharmacol. 2024 Jul 11;15:1416781. doi: 10.3389/fphar.2024.1416781. PMID: 39076592; PMCID: PMC11284502. 10: Abd Haghighi MJ, Azadbakht M, Habibi E, Vahedi L, Hosseinimehr SJ. Phytochemical profile, antioxidant, and wound healing activities of Echium amoenum (Boraginaceae). Nat Prod Res. 2024 Jul 27:1-7. doi: 10.1080/14786419.2024.2384079. Epub ahead of print. PMID: 39066567. 11: Zhao Q, Wang K, Hou L, Guo L, Liu X. Based on network pharmacology and molecular docking to explore the potential mechanism of shikonin in periodontitis. BMC Oral Health. 2024 Jul 24;24(1):839. doi: 10.1186/s12903-024-04618-7. PMID: 39048977; PMCID: PMC11270799. 12: Ahmad Bhat N, Gani A, Gani A. Identification, quantification and nutraceutical evaluation of the extracts from Arnebia benthamii roots of Himalayan regions of J&K, India. Ultrason Sonochem. 2024 Oct;109:106985. doi: 10.1016/j.ultsonch.2024.106985. Epub 2024 Jul 9. PMID: 39047460; PMCID: PMC11321380. 13: Guo C, Li Y, Zhang H, Zhang Q, Wu X, Wang Y, Sun F, Shi S, Xia X. A review on improving the sensitivity and color stability of naturally sourced pH- sensitive indicator films. Compr Rev Food Sci Food Saf. 2024 Jul;23(4):e13390. doi: 10.1111/1541-4337.13390. PMID: 39031881. 14: Elimam H, Alhamshry NAA, Hatawsh A, Elfar N, Moussa R, Radwan AF, Abd- Elmawla MA, Elkashlan AM, Zaki MB, Abdel-Reheim MA, Mohammed OA, Doghish AS. Natural products and long noncoding RNA signatures in gallbladder cancer: a review focuses on pathogenesis, diagnosis, and drug resistance. Naunyn Schmiedebergs Arch Pharmacol. 2024 Jul 19. doi: 10.1007/s00210-024-03279-1. Epub ahead of print. PMID: 39028332. 15: Shi C, Qi Z, Yang C, Luo S, Huang S, Luo Y. Shikonin ameliorates depressive- and anxiogenic-like behaviors in rats via the suppression of inflammation in the hippocampus. Neurosci Lett. 2024 Aug 10;837:137893. doi: 10.1016/j.neulet.2024.137893. Epub 2024 Jul 10. PMID: 38997082. 16: Diane A, Ben Tahar S, El Mrabet A, Rabie R, Saffaj T, Ihssane B. QSAR modeling for cytotoxicity of sulfur-containing Shikonin oxime derivatives targeting HCT-15, MGC-803, BEL-7402, and MCF-7 cell lines. Toxicol In Vitro. 2024 Oct;100:105892. doi: 10.1016/j.tiv.2024.105892. Epub 2024 Jul 10. PMID: 38996828. 17: Lu Y, Zhou H, Han C, Gong Y, Li Y, Xia Y, Liang B, Yang H, Wang Z. Enhanced therapeutic impact of Shikonin-encapsulated exosomes in the inhibition of colorectal cancer progression. Nanotechnology. 2024 Jul 23;35(41). doi: 10.1088/1361-6528/ad61f2. PMID: 38991510. 18: Al Azzani M, Nizami ZN, Magramane R, Sekkal MN, Eid AH, Al Dhaheri Y, Iratni R. Phytochemical-mediated modulation of autophagy and endoplasmic reticulum stress as a cancer therapeutic approach. Phytother Res. 2024 Jul 3. doi: 10.1002/ptr.8283. Epub ahead of print. PMID: 38961675. 19: Liu T, Zheng N, Ma Y, Zhang Y, Lei H, Zhen X, Wang Y, Gou D, Zhao J. Recent advancements in chitosan-based intelligent food freshness indicators: Categorization, advantages, and applications. Int J Biol Macromol. 2024 Aug;275(Pt 1):133554. doi: 10.1016/j.ijbiomac.2024.133554. Epub 2024 Jun 29. PMID: 38950804. 20: Chiu I, Yang T. Biopolymer-based intelligent packaging integrated with natural colourimetric sensors for food safety and sustainability. Anal Sci Adv. 2024 Apr 7;5(5-6):e2300065. doi: 10.1002/ansa.202300065. PMID: 38948319; PMCID: PMC11210745.