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Deoxyshikonin

Cat No.:V19592 Purity: ≥98%
Deoxyshikonin is extracted from Arnebia euchroma and has anti-tumor activity.
Deoxyshikonin
Deoxyshikonin Chemical Structure CAS No.: 43043-74-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Deoxyshikonin is extracted from Arnebia euchroma and has anti-tumor activity. Deoxyshikonin increases the expression of VEGF-C and VEGF-A mRNA in HMVEC-dLy, promotes the interaction of HIF-1α and HIF-1β subunits, and binds to HIF-specific DNA sequences. Deoxyshikonin has pro-angiogenic effects in vitro. Deoxyshikonin showed significant synergistic antimicrobial effect against S. pneumonia (MIC =17μg/mL) and also showed significant inhibitory activity against MRSA.
Deoxyshikonin (CAS 43043-74-9) is a naphthoquinone compound extracted from Arnebia euchroma. It is an antibacterial agent that exhibits significant activity against methicillin-resistant Staphylococcus aureus (MRSA) and Streptococcus pneumoniae, with a minimum inhibitory concentration (MIC) of 17 μg/mL. Deoxyshikonin has antioxidant, anti-inflammatory, and anticancer effects.
Biological Activity I Assay Protocols (From Reference)
Targets
Deoxyshikonin increases the expression of VEGF-C and VEGF-A mRNA in HMVEC-dLy, promotes HIF-1α and HIF-1β subunit interaction, and binds to HIF-specific DNA sequences, indicating a pro-lymphangiogenic as well as a pro-angiogenic effect in vitro. It inhibits colorectal cancer (CRC) through the PI3K/Akt/mTOR pathway.
ln Vitro
In vitro, deoxyshikonin shows significant synergic antimicrobial activity against S. pneumoniae (MIC=17 μg/mL) and also shows significantly inhibitory activities against MRSA. It has pro-angiogenic and pro-lymphangiogenic effects. It inhibits colorectal cancer through the PI3K/Akt/mTOR pathway.
ln Vivo
In vivo, deoxyshikonin has been studied for its potential therapeutic applications in skin regeneration, wound healing, and as an antimicrobial agent. Its anti-tumor activity has been demonstrated in various preclinical models.
Enzyme Assay
In vitro enzyme/receptor binding assays for deoxyshikonin are not standard. Its effects on HIF-1α and VEGF expression can be assessed using molecular biology techniques such as qRT-PCR and Western blotting. Its antimicrobial activity is assessed using standard susceptibility testing methods.
Cell Assay
Cell-based assays for deoxyshikonin involve treating cancer cell lines with the compound and measuring cell proliferation, apoptosis, and signaling pathway activation. Its effects on the PI3K/Akt/mTOR pathway are evaluated by measuring the phosphorylation status of key proteins. Its pro-angiogenic effects are assessed in endothelial cell models.
Animal Protocol
In vivo animal studies for deoxyshikonin are conducted in models of cancer, infection, and wound healing. The compound is administered orally or topically, and its effects on tumor growth, bacterial load, and wound closure are assessed.
ADME/Pharmacokinetics
Deoxyshikonin has a molecular weight of 272.30 and a molecular formula of C16H16O4. It is soluble in DMSO. For storage, it should be kept at -20°C.
Toxicity/Toxicokinetics
The toxicological profile of deoxyshikonin has not been extensively characterized. As a natural naphthoquinone, it may have cytotoxic effects at high concentrations. As with any research compound, appropriate safety precautions should be taken when handling it.
References

[1]. Enhancement of Lymphangiogenesis In Vitro via the Regulations of HIF-1α Expression and Nuclear Translocation by Deoxyshikonin. Evid Based Complement Alternat Med. 2013;2013:148297.

[2]. Antibacterial effects of Traditional Chinese Medicine monomers against Streptococcus pneumoniae via inhibiting pneumococcal histidine kinase (VicK). Front Microbiol. 2015 May 20;6:479.

[3]. Deoxyshikonin isolated from Arnebia euchromainhibits colorectal cancer by down-regulating the PI3K/Akt/mTOR pathway. Pharm Biol. 2019 Dec;57(1):412-423.

Additional Infomation
Deoxyshikonin is a hydroxy-1,4-naphthoquinone. Deoxyshikonin has been reported in Lithospermum erythrorhizon, Lithospermum verum, and other organisms for which data are available. See also: Lithospermum erythrorhizon root (partial); ...).
Deoxyshikonin is a naphthoquinone compound with antibacterial, antioxidant, anti-inflammatory, and anticancer effects. It is active against MRSA and S. pneumoniae. It promotes angiogenesis and lymphangiogenesis through HIF-1α and VEGF. It is a valuable research tool for studying cancer, angiogenesis, and infectious diseases.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H16O4
Molecular Weight
272.2958
Exact Mass
272.104
CAS #
43043-74-9
PubChem CID
98914
Appearance
Brown to reddish brown solid powder
Density
1.3±0.1 g/cm3
Boiling Point
503.7±50.0 °C at 760 mmHg
Melting Point
91ºC
Flash Point
272.5±26.6 °C
Vapour Pressure
0.0±1.3 mmHg at 25°C
Index of Refraction
1.611
LogP
4.72
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Heavy Atom Count
20
Complexity
471
Defined Atom Stereocenter Count
0
InChi Key
VOMDIEGPEURZJO-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H16O4/c1-9(2)4-3-5-10-8-13(19)14-11(17)6-7-12(18)15(14)16(10)20/h4,6-8,17-18H,3,5H2,1-2H3
Chemical Name
5,8-dihydroxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~33.33 mg/mL (~122.40 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.18 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (9.18 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.6724 mL 18.3621 mL 36.7242 mL
5 mM 0.7345 mL 3.6724 mL 7.3448 mL
10 mM 0.3672 mL 1.8362 mL 3.6724 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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