| Size | Price | Stock | Qty |
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| 100mg |
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| 500mg |
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| 1g |
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| Other Sizes |
| Targets |
Tubulin polymerization (IC50 = 4 μM)
cis-Trismethoxy resveratrol targets tubulin, the protein that polymerizes to form microtubules. By inhibiting tubulin polymerization, the compound disrupts the microtubule network essential for cell division, leading to anti-mitotic effects. The compound is a cis isomer of 3,5,4'-trimethoxystilbene and exhibits potent anti-mitotic activity. |
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| ln Vitro |
Resveratrol (3,5,4'-trihydroxystilbene) a natural polyphenol present in medicinal plants, grapes and wines, has potent chemopreventive properties on intestinal carcinogenesis. A methylated derivative (Z-3,5,4'-trimethoxystilbene: R3) was synthesized. R3 at 0.3 microM exerted a 80% growth inhibition of human colon cancer Caco-2 cells and arrested growth completely at 0.4 microM (R3 was 100-fold more active than resveratrol). The cis conformation of R3 was also 100-fold more potent than the trans isomer. R3 (0.3 microM) caused cell cycle arrest at the G2/M phase transition. The drug inhibited tubulin polymerization in a dose-dependent manner (IC50=4 microM), and it reduced also by 2-fold ornithine decarboxylase and s-adenosylmethionine decarboxylase activities. This caused the depletion of the polyamines, putrescine and spermidine, which are growth factors for cancer cells. R3 inhibited partially colchicine binding to its binding site on tubulin, indicating that R3 either partially overlaps with colchicine binding or that R3 binds to a specific site of tubulin that is not identical with the colchicine binding site modifying colchicine binding by allosteric influences. The resveratrol derivative (Z)-3,5,4'-trimethoxystilbene (R3) is an interesting anti-mitotic drug that exerts cytotoxic effects by depleting the intracellular pool of polyamines and by altering microtubule polymerization. Such a drug may be useful for the treatment of neoplastic diseases.[1]
In cell-free biochemical assays, cis-Trismethoxy resveratrol inhibits tubulin polymerization with an IC50 of 4 μM. This activity demonstrates the compound's direct inhibition of tubulin assembly into microtubules. The compound's anti-mitotic activity is measured using tubulin polymerization assays. |
| ln Vivo |
In cell-based assays, cis-Trismethoxy resveratrol exhibits anti-mitotic activity. The compound inhibits cell division by disrupting the microtubule network, leading to mitotic arrest. The compound also exhibits potent antioxidant activity. The compound's effects on cell cycle progression and cell viability are evaluated in cell culture models.
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| Enzyme Assay |
The cell-free tubulin polymerization assay involves incubation of purified tubulin with the compound at various concentrations in assembly buffer containing GTP. The reaction is incubated at 37°C, and microtubule polymerization is monitored by measuring absorbance at 340 nm. The IC50 of 4 μM for inhibition of tubulin polymerization is determined from dose-response curves.
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| Cell Assay |
Cell-based assays for anti-mitotic activity involve culturing mammalian cells and treating them with cis-Trismethoxy resveratrol at concentrations ranging from 0.1 to 50 μM. Cells are incubated for 24-72 hours, and the effect on the microtubule network is assessed by immunofluorescence staining of tubulin. Cell cycle analysis by flow cytometry is performed to assess mitotic arrest. Cell viability is assessed using MTT or CCK-8 assays.
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| Animal Protocol |
There is no established animal experimental protocol for cis-Trismethoxy resveratrol specifically. As an anti-mitotic agent and microtubule inhibitor, the compound could potentially be evaluated in animal models of cancer. Typical protocols for microtubule inhibitors involve administration to tumor-bearing mice via intraperitoneal or intravenous routes.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of cis-Trismethoxy resveratrol have not been extensively reported. As a small molecule with molecular weight of 270.32 g/mol, the compound would be expected to have moderate oral bioavailability and reasonable tissue penetration. The compound is a cis isomer of 3,5,4'-trimethoxystilbene. Further pharmacokinetic studies would be required to determine plasma half-life, clearance, and metabolic pathways.
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| Toxicity/Toxicokinetics |
Toxicity data for cis-Trismethoxy resveratrol are not well documented. As an anti-mitotic agent, the compound would be expected to have toxicity toward rapidly dividing cells, which could translate to bone marrow suppression, gastrointestinal toxicity, and other effects. Standard toxicity studies would be required to determine the safety profile.
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| References | |
| Additional Infomation |
cis-Trismethoxy resveratrol is a research compound used to study microtubule inhibition and anti-mitotic activity. It is the cis isomer of 3,5,4'-trimethoxystilbene and is a potent antioxidant found in grapes and red wine. The compound inhibits tubulin polymerization with an IC50 of 4 μM. It is not an approved pharmaceutical and has no clinical trial history. This product is intended for research use only and is not for human therapeutic applications.
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| Molecular Formula |
C17H18O3
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|---|---|
| Molecular Weight |
270.323025226593
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| Exact Mass |
270.125
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| CAS # |
94608-23-8
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| PubChem CID |
9878556
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
423.8±35.0 °C at 760 mmHg
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| Flash Point |
144.4±23.2 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.600
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| LogP |
4.61
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
20
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| Complexity |
283
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C(/C1C=C(OC)C=C(OC)C=1)=C/C1C=CC(OC)=CC=1
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| InChi Key |
GDHNBPHYVRHYCC-PLNGDYQASA-N
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| InChi Code |
InChI=1S/C17H18O3/c1-18-15-8-6-13(7-9-15)4-5-14-10-16(19-2)12-17(11-14)20-3/h4-12H,1-3H3/b5-4-
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| Chemical Name |
1,3-dimethoxy-5-[(Z)-2-(4-methoxyphenyl)ethenyl]benzene
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| Synonyms |
cis-trismethoxy Resveratrol; 94608-23-8; (Z)-3,5,4'-TRIMETHOXYSTILBENE; CHEMBL311636; 1,3-dimethoxy-5-[(Z)-2-(4-methoxyphenyl)ethenyl]benzene; cis-trismethoxy Resveratrol (Solution in Ethanol); CIS-TRIMETHOXY STILBENE; (Z)-3,4',5-trimethoxystilbene;
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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 | 3.6993 mL | 18.4966 mL | 36.9932 mL | |
| 5 mM | 0.7399 mL | 3.6993 mL | 7.3986 mL | |
| 10 mM | 0.3699 mL | 1.8497 mL | 3.6993 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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