| Size | Price | Stock | Qty |
|---|---|---|---|
| 1g |
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| Other Sizes |
| Targets |
Tulipalin A acts as a potent Michael acceptor, covalently binding to thiol groups in proteins and glutathione. This leads to oxidative stress, apoptosis, and inhibition of DNA synthesis. It inhibits topoisomerase II and triggers mitochondrial dysfunction. It also activates the Nrf2 pathway as an adaptive response.
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|---|---|
| ln Vitro |
In vitro, tulipalin A shows cytotoxicity against various cancer cell lines with IC50 values around 5-10 µM. It also exhibits antibacterial activity against S. aureus (MIC 32 µg/mL). It induces apoptosis and ROS generation in HeLa cells at 10 µM. It also activates caspase-3 and -9.
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| ln Vivo |
In vivo, tulipalin A is toxic; it causes skin irritation and allergic reactions. In mouse models, intraperitoneal administration of 10 mg/kg caused hepatotoxicity and weight loss. Its anticancer potential is limited by its high systemic toxicity. No therapeutic use is feasible.
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| Enzyme Assay |
The in vitro cytotoxicity assay uses MTT on HeLa cells. For enzyme inhibition, topoisomerase II activity is assessed by DNA relaxation assay. Covalent binding to glutathione is measured by HPLC after incubation.
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| Cell Assay |
For in vitro cell-based assays, HeLa cells are treated with tulipalin A (1-20 µM) for 24 h. Cell viability, ROS, and apoptosis are measured. For antibacterial, broth microdilution is performed.
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| Animal Protocol |
In vivo toxicity studies: mice are given tulipalin A i.p. at 5, 10, 20 mg/kg, and survival, organ weights, and histopathology are assessed. For contact dermatitis, guinea pigs are exposed topically to tulipalin A.
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| ADME/Pharmacokinetics |
Pharmacokinetic data are scarce. It is rapidly absorbed and distributed. It forms adducts with glutathione and is excreted as mercapturic acids. Half-life is short (1-2 h).
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| Toxicity/Toxicokinetics |
Tulipalin A is highly toxic; LD50 in mice ~ 15 mg/kg (i.p.). It is a strong allergen and sensitizer. Carcinogenicity data are limited. It is not suitable for human use.
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| References | |
| Additional Infomation |
α-Methylene-γ-butyrolactone is a but-4-lactone with a methylene group at the 3-position. It is used as a gastrointestinal drug and an anti-ulcer agent. α-Methylene-γ-butyrolactone has been reported in Tulipa patens, Tulipa clusiana, and other organisms with relevant data.
Tulipalin A is a cause of "tulip fingers" in florists. It has been studied as a potential cytotoxic agent, but its toxicity precludes clinical use. It is used as a research tool for studying Michael addition biology. |
| Molecular Formula |
C5H6O2
|
|---|---|
| Molecular Weight |
98.09994
|
| Exact Mass |
98.036
|
| CAS # |
547-65-9
|
| Related CAS # |
70748-25-3
|
| PubChem CID |
68352
|
| Appearance |
Colorless to light yellow liquid
|
| Density |
1.1±0.1 g/cm3
|
| Boiling Point |
204.4±0.0 °C at 760 mmHg
|
| Flash Point |
37.2±0.0 °C
|
| Vapour Pressure |
0.3±0.4 mmHg at 25°C
|
| Index of Refraction |
1.452
|
| LogP |
-0.06
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
7
|
| Complexity |
115
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C=C1CCOC1=O
|
| InChi Key |
GSLDEZOOOSBFGP-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2
|
| Chemical Name |
3-methylideneoxolan-2-one
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ≥ 100 mg/mL (~1019.37 mM)
|
|---|---|
| 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 | 10.1937 mL | 50.9684 mL | 101.9368 mL | |
| 5 mM | 2.0387 mL | 10.1937 mL | 20.3874 mL | |
| 10 mM | 1.0194 mL | 5.0968 mL | 10.1937 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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