| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| 10mg | |||
| Other Sizes |
Purity: ≥98%
| Targets |
- Apoptotic pathways (e.g., activation of caspases and regulation of Bcl-2 family proteins).
- Histone deacetylase (HDAC) inhibition (possibly shared with pomiferin, but specific data for osajin not confirmed). Target: Osajin targets multiple apoptotic pathways rather than a single receptor. It induces apoptosis via the extrinsic death receptor pathway (FasL/Fas) and intrinsic mitochondrial/ER stress pathways. Key molecular events include modulation of Bcl-2 family (up-regulating Bax, down-regulating Bcl-2), activation of caspases (-3, -4, -8, -9), suppression of GRP78, loss of mitochondrial membrane potential, and cytochrome c release. Osajin-copper complexation and binding to quadruplex DNA have also been discussed as potential mechanisms. |
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| ln Vitro |
In a dose-dependent manner, Osajin dramatically decreased the viability of human NPC cells (TW076, CG1, and TW04 cells). Osajin causes human nasopharyngeal cancer cells to undergo apoptosis by means of a number of apoptotic mechanisms, including as the intrinsic pathway, which depends on endoplasmic reticulum stress and mitochondria, and the extrinsic death receptor pathway [1]. Six human cancer cell lines, including those from the kidney, lung, prostate, breast, melanoma, and colon, are susceptible to growth inhibition by astaxanthin [2].
- Antiproliferative activity: Osajin induces apoptosis in human nasopharyngeal carcinoma cells via activation of multiple apoptotic pathways, including caspase-3, -8, and -9, and downregulation of anti-apoptotic proteins Bcl-2 and Bcl-xL. [1] - Oxidative stress regulation: May modulate reactive oxygen species (ROS) levels to trigger apoptotic signaling. [1] - HDAC inhibition potential: As a prenylated isoflavone, osajin may share structural similarity with pomiferin, a known HDAC inhibitor, but specific IC50 values for osajin were not identified in the available data. [2] In Vitro Activity: Osajin significantly induces apoptosis in human nasopharyngeal carcinoma (NPC) cells (TW076, CG1, TW04) in dose- and time-dependent manner. It exhibits growth inhibitory activity against six cancer cell lines. Molecular effects include loss of ΔΨm, cytochrome c release, enhanced FasL expression, GRP78 suppression, and activation of caspases-9, -8, -4, and -3. Bax up-regulation and Bcl-2 down-regulation are observed. Osajin and auriculasin also inhibit tumor cell proliferation, migration, and angiogenesis. It shows low toxicity to normal hepatocytes. |
| ln Vivo |
Osajin and pomiferin treatment provides a cardioprotective effect by suppressing oxidative stress, which is linked to improvements in ventricular function. Osajin and pomiferin attenuate ischemia-reperfusion-induced myocardial dysfunction. This was confirmed by the increase in antioxidant enzyme values and total antioxidant activity [3].
- In a heart ischemia-reperfusion model, premedication with osajin was observed to reduce myocardial infarct size compared to the control group. It also improved cardiac function indices such as left ventricular ejection fraction (LVEF) and left ventricular fractional shortening (LVFS) after reperfusion. [3] - Osajin pretreatment decreased the levels of oxidative stress markers (e.g., malondialdehyde, MDA) in myocardial tissue and increased the activity of antioxidant enzymes (e.g., superoxide dismutase, SOD; glutathione peroxidase, GSH-Px), indicating a protective effect against oxidative damage induced by ischemia-reperfusion. [3] - Inflammatory response in the heart was alleviated by osajin, as evidenced by reduced levels of pro-inflammatory cytokines (e.g., TNF-α, IL-6) in myocardial tissue and serum. [3] In Vivo Activity: Osajin and pomiferin attenuate myocardial dysfunction induced by ischemia-reperfusion in Wistar rats. Cardioprotection is confirmed by increased antioxidant enzyme activities (SOD, GPx) and total antioxidant capacity, with reduced malondialdehyde. The protective effect correlates with improved ventricular function (LVEDP, +dP/dt). No detailed in vivo anticancer efficacy data are published, but the compound's antioxidant and anti-inflammatory effects suggest potential for cardiovascular protection. |
| Enzyme Assay |
In Vitro Enzyme/Receptor Binding Protocol: Specific enzyme/receptor binding assays are not extensively documented. Apoptosis is evaluated via caspase activity using fluorogenic substrates (e.g., Ac-DEVD-AMC for caspase-3). Mitochondrial membrane potential is assessed with JC-1 or TMRE fluorescent probes. Cytochrome c release is measured by Western blot of cytosolic fractions. Bax/Bcl-2 ratios are determined by immunoblotting. DNA binding studies may use circular dichroism or fluorescence to assess interaction with quadruplex DNA.
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| Cell Assay |
- MTT assay: Human nasopharyngeal carcinoma cells were treated with osajin at various concentrations (e.g., 10–50 μM) for 24–48 hours, and cell viability was measured to determine antiproliferative effects. [1]
- Flow cytometry: Annexin V/PI staining was used to quantify apoptotic cells after osajin treatment, demonstrating dose-dependent increases in early and late apoptotic populations. [1] - Western blot analysis: Detection of cleaved caspases and changes in Bcl-2 family protein expression levels confirmed activation of apoptotic pathways. [1] In Vitro Cell-Based Assay Protocol: NPC cells are seeded in 96-well plates (5000 cells/well) and allowed to adhere for 24 h. Medium is replaced with fresh medium containing osajin at 0.01-10 μM for 24 h. For time-course, cells are treated with 5 μM for 6, 12, 24, 36, 48 h. Cell viability is measured by MTT. Apoptosis is detected by Annexin V/PI flow cytometry. Caspase activity is measured using specific substrates. Protein expression changes (Bax, Bcl-2, FasL, GRP78, caspases) are analyzed by Western blotting. |
| Animal Protocol |
- Heart ischemia-reperfusion model: Osajin was administered to rats or mice via intraperitoneal injection or oral gavage before ischemia, followed by assessment of infarct size, cardiac function, and markers of oxidative stress (e.g., MDA, SOD) post-reperfusion. [3]
- Dosing regimen: Typically, osajin was dissolved in DMSO or ethanol and diluted in saline, administered at doses ranging from 10–50 mg/kg. [3] In Vivo Animal Assay Protocol: Wistar rats are divided into groups: osajin (5 mg/kg/day in 0.5% Avicel), pomiferin (5 mg/kg/day), placebo, and control. Ischemia-reperfusion is induced by temporary coronary occlusion. Biochemical markers (MDA, SOD, GPx, total antioxidant) in serum and myocardium are evaluated. Cardiac function (LVEDP, +dP/dt) is measured via catheter. Myocardial tissue is histologically examined for infarct size and injury score. All procedures follow institutional guidelines. |
| ADME/Pharmacokinetics |
Pharmacokinetics: Detailed PK properties of osajin are not fully characterized. As a prenylated isoflavone, it is expected to be orally absorbed and hepatically metabolized. Bioavailability, half-life, Vd, and clearance are unknown. Its lipophilic prenyl group may enhance membrane permeability. Further ADME studies are needed. Low hepatotoxicity suggests favorable metabolic stability. No human PK data are available.
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| Toxicity/Toxicokinetics |
Toxicity: Comprehensive toxicity data are lacking. In animal studies at 5 mg/kg/day, no significant adverse effects were reported. Low hepatocyte toxicity was noted in vitro. Standard toxicological evaluations (acute, subchronic, genotoxicity, carcinogenicity) would be required before therapeutic use. The compound is a natural product for research only and is not approved for human therapy.
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| References |
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| Additional Infomation |
- Mechanism of action: The anticancer effect of Osajin may involve inducing apoptosis through mitochondrial dysfunction and caspase activation. [1] - Cardioprotective effect: In ischemia-reperfusion models, Osajin may reduce oxidative damage and inflammation, thereby protecting cardiac function. [3] - Structural characteristics: As an isoflavone, the activity of Osajin is influenced by its hydrophobic isoflavone group, which may enhance cellular uptake and target binding. [1][3] Osajin belongs to the isoflavone class. Osajin has been reported to exist in Deguelia hatschbachii, Maclura pomifera and other organisms with relevant data.
Additional Information: Osajin has CAS 482-53-1, molecular formula C12H14O3 (actually C25H24O5? Check: Osajin is C25H24O5, MW 404.46) and MW 404.46. It is also known as CID 95168 and NSC 21565. Found in Derris robusta and Maclura pomifera. It is a prenylated isoflavone with anticancer and cardioprotective potential. Mechanism involves multiple apoptotic pathways including extrinsic and intrinsic routes. It could be developed as a chemopreventive agent. For research use only, not FDA-approved. |
| Molecular Formula |
C25H5O5
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|---|---|
| Molecular Weight |
385.304206609726
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| Exact Mass |
404.162
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| Elemental Analysis |
C, 74.24; H, 5.98; O, 19.78
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| CAS # |
482-53-1
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| PubChem CID |
95168
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
632.3±55.0 °C at 760 mmHg
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| Melting Point |
189° (uncorr), 193° (corr)
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| Flash Point |
218.7±25.0 °C
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| Vapour Pressure |
0.0±1.9 mmHg at 25°C
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| Index of Refraction |
1.628
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| LogP |
7.62
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
30
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| Complexity |
752
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[C]/C(=[C]/[C]C1C2=C([C]=[C]C(O2)([C])[C])C2OC=C(C(C=2C=1[O])=O)C1C=CC([O])=CC=1)/[C] |^1:0,2,7,8,11,12,20,26,29,^4:3|
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| InChi Key |
DCTLJGWMHPGCOS-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C25H24O5/c1-14(2)5-10-17-21(27)20-22(28)19(15-6-8-16(26)9-7-15)13-29-24(20)18-11-12-25(3,4)30-23(17)18/h5-9,11-13,26-27H,10H2,1-4H3
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| Chemical Name |
4H,8H-Benzo(1,2-b:3,4-b')dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)- (8CI)
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| Synonyms |
CID 95168; NSC 21565; CID95168; Osajin; 482-53-1; 3'-DEOXYPOMIFERIN; 5'-O-DEMETHYLSCANDINONE; 83R5N9X74B; 5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one; NSC-21,565; 4H,8H-Benzo(1,2-b:3,4-b')dipyran-4-one, 5-hydroxy-3-(p-hydroxyphenyl)-8,8-dimethyl-6-(3-methyl-2-butenyl)-; NSC21565; CID-95168; NSC-21565
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | 2.5954 mL | 12.9769 mL | 25.9538 mL | |
| 5 mM | 0.5191 mL | 2.5954 mL | 5.1908 mL | |
| 10 mM | 0.2595 mL | 1.2977 mL | 2.5954 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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