Shikonin | CAS#517-89-5 | PKM2 inhibitor

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

MedKoo CAT#: 561250

CAS#: 517-89-5

Description: 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.

Chemical Structure

Shikonin

CAS# 517-89-5

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 561250
Name: Shikonin
CAS#: 517-89-5
Chemical Formula: C16H16O5
Exact Mass: 288.10
Molecular Weight: 288.300
Elemental Analysis: C, 66.66; H, 5.59; O, 27.75

Price and Availability

Size	Price	Availability
25mg	USD 350	2 Weeks
50mg	USD 600	2 Weeks
100mg	USD 950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	125.0	433.58

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.

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.

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1: Andújar I, Ríos JL, Giner RM, Recio MC. Pharmacological properties of shikonin - a review of literature since 2002. Planta Med. 2013 Dec;79(18):1685-97. doi: 10.1055/s-0033-1350934. Epub 2013 Oct 23. Review. PubMed PMID: 24155261.

2: Andújar I, Recio MC, Giner RM, Ríos JL. Traditional chinese medicine remedy to jury: the pharmacological basis for the use of shikonin as an anticancer therapy. Curr Med Chem. 2013;20(23):2892-8. Review. PubMed PMID: 23651309.

3: Wang R, Yin R, Zhou W, Xu D, Li S. Shikonin and its derivatives: a patent review. Expert Opin Ther Pat. 2012 Sep;22(9):977-97. doi: 10.1517/13543776.2012.709237. Epub 2012 Jul 27. Review. PubMed PMID: 22834677.

4: Malik S, Bhushan S, Sharma M, Ahuja PS. Biotechnological approaches to the production of shikonins: a critical review with recent updates. Crit Rev Biotechnol. 2016;36(2):327-40. doi: 10.3109/07388551.2014.961003. Epub 2014 Oct 16. Review. PubMed PMID: 25319455.

5: Zhu MY, Wang RB, Zhou W, Li SS. [Antitumor effect research progress of shikonin and its derivatives]. Yao Xue Xue Bao. 2012 May;47(5):588-93. Review. Chinese. PubMed PMID: 22812000.

6: Chen X, Yang L, Oppenheim JJ, Howard MZ. Cellular pharmacology studies of shikonin derivatives. Phytother Res. 2002 May;16(3):199-209. Review. PubMed PMID: 12164262.

7: Papageorgiou VP, Assimopoulou AN, Ballis AC. Alkannins and shikonins: a new class of wound healing agents. Curr Med Chem. 2008;15(30):3248-67. Review. PubMed PMID: 19075667.

8: Vandenberk L, Belmans J, Van Woensel M, Riva M, Van Gool SW. Exploiting the Immunogenic Potential of Cancer Cells for Improved Dendritic Cell Vaccines. Front Immunol. 2016 Jan 14;6:663. doi: 10.3389/fimmu.2015.00663. eCollection 2015. Review. PubMed PMID: 26834740; PubMed Central PMCID: PMC4712296.

9: Nakaya K, Miyasaka T. A shikonin derivative, beta-hydroxyisovalerylshikonin, is an ATP-non-competitive inhibitor of protein tyrosine kinases. Anticancer Drugs. 2003 Oct;14(9):683-93. Review. PubMed PMID: 14551501.

10: Lu JJ, Bao JL, Wu GS, Xu WS, Huang MQ, Chen XP, Wang YT. Quinones derived from plant secondary metabolites as anti-cancer agents. Anticancer Agents Med Chem. 2013 Mar;13(3):456-63. Review. PubMed PMID: 22931417.

11: Fan HX, Zhu WH. [Tissue cultures of Lithospermum erythrorhizon and biosynthesis of shikonin derivatives]. Yao Xue Xue Bao. 1988;23(9):716-20. Review. Chinese. PubMed PMID: 3076738.

12: Kumar N, Kumar R, Kishore K. Onosma L.: A review of phytochemistry and ethnopharmacology. Pharmacogn Rev. 2013 Jul;7(14):140-51. doi: 10.4103/0973-7847.120513. Review. PubMed PMID: 24347922; PubMed Central PMCID: PMC3841992.

13: Ghosh N, Ghosh R, Bhat ZA, Mandal V, Bachar SC, Nima ND, Sunday OO, Mandal SC. Advances in herbal medicine for treatment of ischemic brain injury. Nat Prod Commun. 2014 Jul;9(7):1045-55. Review. PubMed PMID: 25230523.

14: Yang H, Liu J, Dou QP. Targeting tumor proteasome with traditional Chinese medicine. Curr Drug Discov Technol. 2010 Mar;7(1):46-53. Review. PubMed PMID: 20156140; PubMed Central PMCID: PMC3306007.

15: Inoue K. [Cytochrome P450 enzymes in biosyntheses of some plant secondary metabolites]. Yakugaku Zasshi. 2005 Jan;125(1):31-49. Review. Japanese. PubMed PMID: 15635280.

16: Vaishnav P, Demain AL. Unexpected applications of secondary metabolites. Biotechnol Adv. 2011 Mar-Apr;29(2):223-9. doi: 10.1016/j.biotechadv.2010.11.006. Epub 2010 Dec 3. Review. PubMed PMID: 21130862.

17: Poronnik OA, Kunakh VA. [Biosynthesis of naphthoquinoine pigments in plants from Boraginaceae family in nature and in vitro culture]. Ukr Biokhim Zh (1999). 2005;77(6):24-36. Review. Russian. PubMed PMID: 19618739.

18: Wang R, Zhou S, Li S. Cancer therapeutic agents targeting hypoxia-inducible factor-1. Curr Med Chem. 2011;18(21):3168-89. Review. PubMed PMID: 21671859.

19: Mohammadi A, Mansoori B, Baradaran B. Regulation of miRNAs by herbal medicine: An emerging field in cancer therapies. Biomed Pharmacother. 2017 Feb;86:262-270. doi: 10.1016/j.biopha.2016.12.023. Epub 2016 Dec 19. Review. PubMed PMID: 28006752.

20: Hazra B, Das Sarma M, Sanyal U. Separation methods of quinonoid constituents of plants used in Oriental traditional medicines. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Dec 5;812(1-2):259-75. Review. PubMed PMID: 15556503.

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