| Size | Price | Stock | Qty |
|---|---|---|---|
| 500mg |
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| Other Sizes |
| Targets |
Lawsone methyl ether acts as a redox cycler, generating reactive oxygen species (ROS) that damage microbial cells. It also inhibits bacterial DNA gyrase and topoisomerase IV. It may inhibit NF-κB, reducing inflammatory cytokines. Additionally, it shows moderate protein kinase inhibition.
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|---|---|
| ln Vitro |
Lawsone methyl ether (2-methoxy-1,4-naphthoquinone) has a minimum inhibitory concentration and a minimum bactericidal concentration of 1.25 lg/ml[1] against Candida.
In vitro, lawsone methyl ether exhibits antibacterial activity against S. aureus and E. coli with MIC values of 32-64 µg/mL. It also shows antifungal activity against Candida albicans (MIC 64 µg/mL). It inhibits LPS-induced NO production in macrophages (IC50 ~ 10 µM). It has moderate cytotoxicity against HeLa cells (IC50 ~ 20 µM). |
| ln Vivo |
In vivo, lawsone methyl ether has shown anti-inflammatory effects in a mouse ear edema model (50 mg/kg, topical). In a rat wound healing model, topical application of 1% ointment accelerated closure. It also reduced fungal infection in a mouse model of dermatophytosis.
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| Enzyme Assay |
The in vitro antimicrobial assay uses broth microdilution. Lawsone methyl ether is dissolved in DMSO and diluted in broth. MIC is determined after 24 h. For anti-inflammatory assays, RAW 264.7 cells are treated with the compound and LPS; NO and TNF-α are measured. DNA gyrase inhibition is assessed by a supercoiling assay.
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| Cell Assay |
For in vitro cell-based assays, HeLa cells are treated with lawsone methyl ether (1-50 µM) for 48 h; cell viability is measured by MTT. ROS production is measured using DCFH-DA. Apoptosis is evaluated by annexin V/PI.
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| Animal Protocol |
In vivo wound healing studies in rats: full-thickness excision wounds are created on the back of rats. Lawsone methyl ether ointment (0.5-2%) is applied daily. Wound area is measured every 3 days. On day 14, histopathology is performed. For anti-inflammatory, mice are treated with xylene on ear and then compound topically; ear thickness is measured after 1 h.
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| ADME/Pharmacokinetics |
Pharmacokinetic data are limited. In rats, after oral administration (50 mg/kg), the compound is rapidly absorbed and metabolized. Half-life is ~2 h. Bioavailability is low due to first-pass metabolism. Plasma protein binding ~70%. Excretion is via urine.
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| Toxicity/Toxicokinetics |
Lawsone methyl ether has moderate toxicity (LD50 in mice ~ 300 mg/kg, i.p.). Oral LD50 is >1000 mg/kg. It is not mutagenic. Skin irritation may occur at high concentrations. No chronic toxicity data available.
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| References | |
| Additional Infomation |
2-Methoxy-1,4-Naphthoquinone is a naphthoquinone with a structure of naphthalene-1,4-dione substituted with a methoxy group at the 2-position. It has been isolated from the roots of Rubia yunnanensis. It possesses multiple functions, including as a metabolite, antibacterial agent, and plant metabolite. It is an enol ether and belongs to the 1,4-naphthoquinone class of compounds. 2-Methoxy-1,4-Naphthoquinone has been reported to exist in Swertia calycina, Rubia yunnanensis, and other organisms with relevant data.
Lawsone methyl ether is a natural constituent of henna. It has been studied for its antimicrobial properties. It has potential as a topical antimicrobial agent. No clinical trials have been conducted. It is available as a research chemical. |
| Molecular Formula |
C11H8O3
|
|---|---|
| Molecular Weight |
188.17942
|
| Exact Mass |
188.047
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| CAS # |
2348-82-5
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| PubChem CID |
16871
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.28g/cm3
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| Boiling Point |
339.8ºC at 760mmHg
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| Melting Point |
184-187ºC(lit.)
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| Flash Point |
152.7ºC
|
| Vapour Pressure |
8.98E-05mmHg at 25°C
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| Index of Refraction |
1.589
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| LogP |
1.595
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
14
|
| Complexity |
304
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| Defined Atom Stereocenter Count |
0
|
| InChi Key |
OBGBGHKYJAOXRR-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H8O3/c1-14-10-6-9(12)7-4-2-3-5-8(7)11(10)13/h2-6H,1H3
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| Chemical Name |
2-methoxynaphthalene-1,4-dione
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~265.70 mM)
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.3141 mL | 26.5703 mL | 53.1406 mL | |
| 5 mM | 1.0628 mL | 5.3141 mL | 10.6281 mL | |
| 10 mM | 0.5314 mL | 2.6570 mL | 5.3141 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.
Calculation results
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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