| Size | Price | |
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| Other Sizes |
| Targets |
Target: SARS‑CoV‑2 main protease (Mpro/3CLpro) – no IC₅₀/Ki/EC₅₀ values reported; docking binding free energy = −34.329 kcal/mol (Glide XP score) [2]
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| ln Vitro |
In vitro, 2-methylanthraquinone (tectoquinone) showed concentration-dependent mosquito larvicidal activity against fourth-instar larvae of Aedes aegypti and Aedes albopictus after 24 h exposure. The LC₅₀ values were 3.3 μg/mL for A. aegypti and 5.4 μg/mL for A. albopictus; the LC₉₀ values were 8.8 μg/mL for A. aegypti and 26.9 μg/mL for A. albopictus [1].
In structure-activity comparisons among anthraquinone congeners, 2-methylanthraquinone exhibited the strongest mosquito larvicidal activity. Anthraquinone, alizarin (1,2-dihydroxyanthraquinone), and 1-hydroxyanthraquinone showed no activity (LC₅₀ > 25 μg/mL). Anthraquinone-2-carboxylic acid had LC₅₀ values of 16.3 μg/mL (A. aegypti) and 17.9 μg/mL (A. albopictus); 2-hydroxymethylanthraquinone had LC₅₀ values of 15.4 μg/mL and 17.0 μg/mL, respectively. Emodin (3-methyl-1,6,8-trihydroxyanthraquinone) also showed strong activity (LC₅₀ 5.3 μg/mL against A. aegypti, 4.2 μg/mL against A. albopictus), but 2-methylanthraquinone was more potent than emodin against A. aegypti (3.3 vs. 5.3 μg/mL) [1]. |
| ln Vivo |
In vivo, 2-methylanthraquinone (tectoquinone) was evaluated for mosquito larvicidal activity using fourth-instar larvae of Aedes aegypti and Aedes albopictus. The compound caused 50% and 90% mortality at the concentrations described (see In Vitro). No mortality was observed in the control groups (DMSO only). The positive control chlorpyrifos had LC₅₀ values of 1.1 μg/mL (A. aegypti) and 1.8 μg/mL (A. albopictus) [1].
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| Enzyme Assay |
Enzyme Assay: No experimental enzyme assays were performed. The study used molecular docking with the GLIDE module of Schrodinger Maestro. The crystal structure of SARS‑CoV‑2 main protease (PDB ID: 6LU7) was retrieved. Protein preparation included adding hydrogen atoms, removing water molecules, building side chains and loops using the prime module, and optimization with the OPLS‑2005 force field. Ligands were prepared using the LigPrep module. A receptor grid was generated around the co‑crystal ligand with a diameter of 20 Å. Docking was performed in extra precision (XP) mode with scaling factor for van der Waals radii ≤0.15. The glide score function includes Coulomb, vdW, site, hydrogen bond, buryP, metal, rotB, and lipophilic terms. The best pose was selected based on glide score. For 2-Methylanthraquinone, the docking score (binding free energy) was −34.329 kcal/mol, with interactions mainly through hydrogen bonding with CYS‑145 and stacking interaction with HIS‑41 [2].
Molecular dynamics (MD) simulation was performed using the Desmond module for 50 ns under NTP conditions. The system included the protein‑ligand complex in a TIP3P water box with orthorhombic geometry, neutralized with 150 mM NaCl. The simulation was run after system relaxation. RMSD, RMSF, and protein‑ligand interactions were analyzed. The MD simulation showed that the 2-Methylanthraquinone‑Mpro complex had RMSD deviations not within acceptable range, indicating unstable interaction. Binding energies were calculated using MMGBSA from frames at 10 ns intervals; average binding energy was −37.21 ± 16 kcal/mol. The main interaction type was hydrophobic contacts [2]. Active site residues of SARS‑CoV‑2 Mpro were identified using the PLIP web server, including residues 143A GLY, 144A SER, 163A HIS, 164A HIS, 166A GLU [2]. |
| Animal Protocol |
Mosquito larvicidal bioassay: Fourth-instar larvae of A. aegypti and A. albopictus (Kaohsiung strain, reared at 27 °C, 12:12 h photoperiod, 80±10% RH, fed with 10% yeast suspension) were used. Ten larvae were placed in 24.5 mL of degassed distilled water in a 30 mL cup. Then 500 μL of DMSO solution containing the test sample (2-methylanthraquinone) was added to achieve final concentrations of 100, 50, 25, 12.5, 6.25, 3.125, 1.56, 0.78, and 0.39 μg/mL. The control received 24.5 mL water and 500 μL DMSO. Each test was replicated four times. Larvicidal activity was evaluated 24 h after treatment. Larvae were considered dead if appendages did not move when prodded. Mortality percentages were corrected using Abbott's formula. LC₅₀ and LC₉₀ values (with 95% confidence limits) were calculated by probit analysis (Finney method) using log/probability paper. Chlorpyrifos was used as a positive control at concentrations of 6.25, 3.125, 1.56, 0.78, and 0.39 μg/mL [1].
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| ADME/Pharmacokinetics |
ADME/Pharmacokinetics: ADME properties were predicted using the SwissADME web tool. 2-Methylanthraquinone obeys all existing drug‑likeness rules including Lipinski’s rule of five (MW ≤500, MLOGP ≤4.15, N or O ≤10, NH or OH ≤5). It is suitable for oral bioavailability. Calculated parameters: lipophilicity (LOGP) = −0.7 to +5.0; molecular weight ~150‑500 g/mol; polarity (TPSA) = 20 Å to 130 Å; Log S (solubility) = 6; fraction Csp3 = 1; number of rotatable bonds = 9. The compound is highly absorbed in the GI tract and is blood‑brain barrier permeant [2].
Target prediction using Swiss Target Prediction indicated that protease is the main target class for 2-Methylanthraquinone, followed by ligand‑gated ion channels and kinases [2]. |
| Toxicity/Toxicokinetics |
Toxicity/Toxicokinetics: Toxicity was evaluated using the pkCSM web server. 2-Methylanthraquinone has no AMES toxicity. The predicted maximum tolerated dose in humans is 0.122 mg/kg/day. Oral acute toxicity (LD₅₀) in rats is 2.11 mol/kg. Oral chronic toxicity (LOAEL) in rats is 2.128 mg/kg_bw/day. The compound has no hepatotoxicity and no skin sensitization. It is not a hERG I or hERG II inhibitor. Predicted T. pyriformis toxicity is 1.302 log μg/L, and Minnow toxicity is 0.86 log mM [2].
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| References |
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| Additional Infomation |
2-Methylanthraquinone is an anthraquinone that is a derivative of 9,10-anthraquinone, in which the hydrogen at the 2-position is replaced by a methyl group. It is functionally related to 9,10-anthraquinone. 2-Methylanthraquinone has been reported in the tea plant (Camellia sinensis), the snakegrass (Rhinacanthus nasutus), and other organisms with relevant data.
Additional Info: 2-Methylanthraquinone (tectoquinone) is a phytoconstituent from Tectona grandis (teak) with known fungicidal and larvicidal properties. In this in silico study, it showed binding affinity to SARS‑CoV‑2 main protease with a docking score of −34.329 kcal/mol, interacting with CYS‑145 and HIS‑41. However, MD simulation over 50 ns indicated that the tectoquinone‑Mpro complex was not stable (RMSD deviations outside acceptable range). Nevertheless, the compound obeys Lipinski’s rule of five and has favorable ADME and low predicted toxicity. The study suggests it as a potential lead for COVID‑19 drug development after further validation [2]. |
| Molecular Formula |
C15H10O2
|
|---|---|
| Molecular Weight |
222.2387
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| Exact Mass |
222.068
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| CAS # |
84-54-8
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| PubChem CID |
6773
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| Appearance |
Off-white to yellow solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
407.8±35.0 °C at 760 mmHg
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| Melting Point |
170-173 °C(lit.)
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| Flash Point |
152.7±22.9 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.644
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| LogP |
3.84
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
|
| Heavy Atom Count |
17
|
| Complexity |
347
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| Defined Atom Stereocenter Count |
0
|
| InChi Key |
NJWGQARXZDRHCD-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C15H10O2/c1-9-6-7-12-13(8-9)15(17)11-5-3-2-4-10(11)14(12)16/h2-8H,1H3
|
| Chemical Name |
2-methylanthracene-9,10-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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 4.4996 mL | 22.4982 mL | 44.9964 mL | |
| 5 mM | 0.8999 mL | 4.4996 mL | 8.9993 mL | |
| 10 mM | 0.4500 mL | 2.2498 mL | 4.4996 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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