| Size | Price | Stock | Qty |
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| 10mg |
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| Targets |
The primary molecular targets of 4-Demethyldeoxypodophyllotoxin are tubulin, which it inhibits from polymerizing into microtubules. This disrupts the mitotic spindle and leads to cell cycle arrest and apoptosis. Some derivatives also exert their anti-tumor effects by inhibiting topoisomerase II. It may also act as a potential selective estrogen receptor α (ERα) inhibiting agent.
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| ln Vitro |
In vitro, 4-Demethyldeoxypodophyllotoxin exhibits significant cytotoxic activity against a wide range of human cancer cell lines, including A549 (human lung carcinoma), SK-MEL-2 (human melanoma), HeLa (cervical cancer), and PC3 (prostate cancer). Its derivatives have demonstrated significant cytotoxic activity, often surpassing the efficacy of clinically used drugs like etoposide (VP-16). It also shows activity against the P-388 lymphocytic leukemia.
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| ln Vivo |
In vivo, 4-Demethyldeoxypodophyllotoxin has been shown to be a tumor inhibitory agent. It exhibits activity against the P-388 lymphocytic leukemia test system. Its derivatives have been investigated as potential selective estrogen receptor α (ERα) inhibiting agents for breast cancer. However, specific in vivo efficacy data are not detailed in the available literature.
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| Enzyme Assay |
Typical in vitro assays for 4-Demethyldeoxypodophyllotoxin include cytotoxicity assays using various cancer cell lines. Cells are cultured in 96-well plates and treated with the compound at various concentrations for 48-72 hours. Cell viability is assessed by MTT or SRB assays, and IC₅₀ values are calculated. Tubulin polymerization assays are performed by monitoring the turbidity of tubulin solutions in the presence of the compound. Topoisomerase II inhibition assays measure the relaxation of supercoiled DNA.
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| Cell Assay |
Cellular assays for 4-Demethyldeoxypodophyllotoxin typically involve treating cancer cell lines (e.g., A549, HeLa, PC3) with the compound at concentrations ranging from 1 nM to 100 µM for 24-72 hours. Cell viability is assessed by MTT assay. Cell cycle analysis is performed by propidium iodide staining and flow cytometry. Apoptosis is evaluated by Annexin V/PI staining and caspase activity measurements. Tubulin polymerization is assessed by immunofluorescence staining of microtubules.
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| Animal Protocol |
In vivo animal experiments for 4-Demethyldeoxypodophyllotoxin are not detailed in the available literature. For antitumor studies, typical animal models include xenograft mouse models where tumor cells are implanted and mice are treated with the compound via intraperitoneal or intravenous injection. Tumor volume, body weight, and survival are monitored. Such studies have been reported for podophyllotoxin derivatives, but specific details for this compound are not available.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 4-Demethyldeoxypodophyllotoxin are limited. As a lignan with a molecular weight of 384.38 g/mol, it would be expected to have moderate oral bioavailability. However, podophyllotoxin derivatives are often administered parenterally. Detailed ADME parameters are not available in the consulted sources.
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| Toxicity/Toxicokinetics |
Toxicological data for 4-Demethyldeoxypodophyllotoxin are limited. As a tubulin inhibitor, it would be expected to have dose-dependent toxicity, particularly affecting rapidly dividing cells. Podophyllotoxin derivatives are known to have significant toxicity. Standard preclinical toxicity studies would be required for therapeutic development. It is intended for research use only.
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| References | |
| Additional Infomation |
4'-Desmethyldeoxypodophyllotoxin belongs to the furanonaphthalene dioxane class of compounds, with the chemical name (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furano[3',4':6,7]naphtho[2,3-d][1,3]dioxane-6(5aH)-one, where the 5-position is substituted with 4-hydroxy-3,5-dimethoxyphenyl. It is a plant metabolite with immunosuppressant, antioxidant, and antitumor activity. It is a lignan, γ-lactone, furanonaphthalene dioxane class of compounds, belonging to the methoxybenzene and phenolic compounds. It has been reported that 4'-desmethyldeoxypodophyllotoxin is found in plants of the Burseraceae family, such as Canarium tonkinense and Dysosma versipellis, as well as other organisms with relevant data.
4-Demethyldeoxypodophyllotoxin is a lignan from Podophyllum species that inhibits tubulin polymerization and exhibits significant cytotoxicity against various cancer cell lines. Its derivatives have shown efficacy surpassing etoposide. It is a research compound for studying anticancer mechanisms and developing new cancer therapies. It is not approved for any clinical indication. |
| Molecular Formula |
C21H20O7
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|---|---|
| Molecular Weight |
384.38
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| Exact Mass |
384.121
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| CAS # |
3590-93-0
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| PubChem CID |
160705
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| Appearance |
White to off-white solid powder
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| LogP |
2.615
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
28
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| Complexity |
583
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| Defined Atom Stereocenter Count |
3
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| SMILES |
COC1=C(C(=CC(=C1)[C@@H]2C3=CC4=C(C=C3C[C@H]5COC(=O)[C@@H]52)OCO4)OC)O
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| InChi Key |
RFDMNXDDRXVJTM-RQUSPXKASA-N
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| InChi Code |
InChI=1S/C21H20O7/c1-24-16-5-11(6-17(25-2)20(16)22)18-13-7-15-14(27-9-28-15)4-10(13)3-12-8-26-21(23)19(12)18/h4-7,12,18-19,22H,3,8-9H2,1-2H3/t12-,18+,19-/m0/s1
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| Chemical Name |
(5R,5aR,8aR)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one
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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 | 2.6016 mL | 13.0080 mL | 26.0159 mL | |
| 5 mM | 0.5203 mL | 2.6016 mL | 5.2032 mL | |
| 10 mM | 0.2602 mL | 1.3008 mL | 2.6016 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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