| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
As a cucurbitacin analogue, 3-epi-Isocucurbitacin B may share similar mechanisms with other cucurbitacins, which often target the STAT3 signaling pathway and actin cytoskeleton. However, for this specific compound, the precise molecular target has not been definitively identified in the available literature. A related compound, isocucurbitacin B, has been shown to directly bind to Caveolin 1 (CAV1) and activate the BKCa calcium channel, suggesting potential targets for this structural class . Further studies are needed to confirm the direct binding targets of 3-epi-Isocucurbitacin B.
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|---|---|
| ln Vitro |
3-epi-Isocucurbitacin B exhibits significant cytotoxicity against a panel of human tumor cell lines. According to the original isolation study, this compound demonstrated potent growth inhibitory effects with exceptionally high potency against A-549 (lung carcinoma), SK-OV-3 (ovarian adenocarcinoma), SK-MEL-2 (skin melanoma), XF-498 (central nervous system tumor), and HCT-15 (colon adenocarcinoma) cells . The cytotoxic activity was observed at sub-micromolar to low micromolar concentrations, consistent with the potent activity typical of cucurbitacin family compounds.
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| ln Vivo |
Related cucurbitacin compounds have demonstrated antitumor activity in animal models. A related compound, isocucurbitacin B, has been shown to effectively suppress tumor growth in an orthotopic glioma mouse model and patient-derived xenograft (PDX) models . These findings suggest that 3-epi-Isocucurbitacin B may have potential for in vivo efficacy, but direct studies are required.
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| Enzyme Assay |
For cucurbitacin compounds, target engagement is often assessed using techniques such as Cellular Thermal Shift Assay (CETSA) to confirm direct binding to putative protein targets like CAV1 . General cucurbitacin cytotoxicity screening uses standard colorimetric assays (e.g., SRB or MTT) following protocols such as those described by Skehan et al. (1990), where cells are exposed to compound for 48-72 hours before fixation and staining .
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| Cell Assay |
The cytotoxicity of 3-epi-Isocucurbitacin B was evaluated using standard in vitro anticancer screening methods. The original study utilized cultured human tumor cell lines including A-549, SK-OV-3, SK-MEL-2, XF-498, and HCT-15 . Cells are typically seeded in 96-well plates and allowed to adhere overnight. Test compound is then added at varying concentrations, and cells are incubated for 48-72 hours. Cell viability is assessed using the SRB (sulforhodamine B) colorimetric method, which measures total cellular protein content .
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| Animal Protocol |
Related compound isocucurbitacin B, in vivo studies have been conducted using an orthotopic glioma mouse model and patient-derived xenograft (PDX) models . These models typically involve implanting tumor cells or patient tumor tissue into immunocompromised mice, followed by compound administration via appropriate routes (e.g., intraperitoneal injection or oral gavage) when tumors reach a certain volume.
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| ADME/Pharmacokinetics |
As a cucurbitane triterpenoid with high lipophilicity (log P values typically >3), the compound is expected to have poor aqueous solubility. For in vivo formulation, solubility enhancers such as DMSO, PEG300, Tween 80, or cyclodextrins are recommended . Common formulation strategies include DMSO:Tween 80:Saline (10:5:85) or DMSO:PEG300:Tween 80:Saline (10:40:5:45) for injection, and 0.5% CMC-Na for oral suspension .
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| Toxicity/Toxicokinetics |
Cucurbitacins as a class are known to exhibit significant cytotoxicity at low concentrations, which underlies their antitumor activity but also raises concerns for potential off-target toxicity .
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| References | |
| Additional Infomation |
According to reports, 3-epiocucurbitacin B has been found in Trichosanthes cucumeroides, Bryonia cretica, and Ipomopsis aggregata, and relevant data are available for reference.
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| Molecular Formula |
C32H46O8
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|---|---|
| Molecular Weight |
558.70
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| Exact Mass |
558.319
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| CAS # |
89647-62-1
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| PubChem CID |
6442968
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
702.4±60.0 °C at 760 mmHg
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| Flash Point |
219.9±26.4 °C
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| Vapour Pressure |
0.0±5.0 mmHg at 25°C
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| Index of Refraction |
1.568
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| LogP |
2.06
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
40
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| Complexity |
1210
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| Defined Atom Stereocenter Count |
9
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| SMILES |
C[C@]12[C@@H]3CC=C4C(C)(C)[C@@H](O)C(=O)C[C@H]4[C@]3(C)C(=O)C[C@@]1([C@H]([C@@H](C2)O)[C@](O)(C)C(=O)/C=C/C(C)(C)OC(=O)C)C
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| InChi Key |
WTBZNVRBNJWSPF-KWPSBSMYSA-N
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| InChi Code |
InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19,21-22,25-26,35,38-39H,11,14-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,26+,29+,30-,31+,32+/m1/s1
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| Chemical Name |
[(E,6R)-6-[(3R,8S,9R,10R,13R,14S,16R,17R)-3,16-dihydroxy-4,4,9,13,14-pentamethyl-2,11-dioxo-3,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
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| Synonyms |
89647-62-1; 3-Epi-Isocucurbitacin B; [(E)-6-(3,16-dihydroxy-4,4,9,13,14-pentamethyl-2,11-dioxo-3,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-hydroxy-2-methyl-5-oxo-hept-3-en-2-yl] acetate; [(E)-6-(3,16-dihydroxy-4,4,9,13,14-pentamethyl-2,11-dioxo-3,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate; Isocucurbitacin B [M+H]+;
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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 | 1.7899 mL | 8.9493 mL | 17.8987 mL | |
| 5 mM | 0.3580 mL | 1.7899 mL | 3.5797 mL | |
| 10 mM | 0.1790 mL | 0.8949 mL | 1.7899 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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