| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| Other Sizes |
| Targets |
Prunasin targets DNA polymerase β. DNA polymerase β is a key enzyme involved in DNA repair, particularly base excision repair. By inhibiting DNA polymerase β, Prunasin interferes with DNA repair processes. The compound is an orally active cyanogenic glucoside and the main metabolite of Amygdalin. It can specifically inhibit rat DNA polymerase β with an IC50 of 98 μM.
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| ln Vitro |
In cell-free biochemical systems, Prunasin inhibits DNA polymerase β activity with an IC50 of 98 μM. This activity demonstrates the compound's direct inhibition of DNA polymerase β enzymatic activity. The compound's ability to inhibit DNA repair makes it a potential tool for studying DNA repair mechanisms and sensitizing cancer cells to DNA-damaging agents.
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| ln Vivo |
In cell-based assays, Prunasin inhibits DNA polymerase β activity, leading to impaired DNA repair. The compound's effects are evaluated in cell lines by assessing DNA repair capacity and cell viability after DNA damage. As a cyanogenic glycoside, Prunasin can also release hydrogen cyanide, which may contribute to its biological effects. The compound's effects on DNA repair and cell survival are assessed.
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| Enzyme Assay |
The cell-free assay for DNA polymerase β inhibition involves measuring the polymerase activity of purified DNA polymerase β in the presence of the compound. The assay uses a DNA template, dNTPs (including labeled dNTPs), and the compound at various concentrations. The incorporation of labeled nucleotides into DNA is measured. The IC50 of 98 μM is determined from dose-response curves.
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| Cell Assay |
Cell-based assays for Prunasin involve culturing cells and treating them with the compound at concentrations ranging from 0.1 to 1000 μM. The compound's effects on DNA repair are assessed by measuring the repair of DNA damage induced by genotoxic agents. Cell viability is assessed using MTT or CCK-8 assays. The compound's effects on cell cycle progression and apoptosis are also evaluated.
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| Animal Protocol |
There is no established animal experimental protocol for Prunasin specifically. As a DNA polymerase β inhibitor and cyanogenic glycoside, the compound could potentially be evaluated in animal models for its effects on DNA repair and cancer. Typical studies involve oral administration of the compound to mice. DNA repair capacity, toxicity, and efficacy are assessed. The compound's cyanogenic potential requires careful monitoring of toxicity.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Organic nitriles are converted into cyanide ions in the liver by cytochrome P450 enzymes. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is primarily metabolized to thiocyanate by thiocyanate oxidase or 3-mercaptopyruvate thiotransferase. Cyanide metabolites are excreted in the urine. (L96) Prunasin is an orally active compound. As a small molecule with a molecular weight of 295.29 g/mol, it would be expected to have moderate oral bioavailability and tissue penetration. The compound is a cyanogenic glycoside and can release hydrogen cyanide, which may affect its pharmacokinetics and toxicity. Further pharmacokinetic studies would be required. |
| Toxicity/Toxicokinetics |
Toxicity Summary
Organic nitriles can decompose into cyanide ions both in vivo and in vitro. Therefore, the main toxic mechanism of organic nitriles is the production of toxic cyanide ions, or hydrogen cyanide. Cyanide ions are inhibitors of cytochrome c oxidase in the fourth electron transport chain complex (located on the mitochondrial membrane of eukaryotic cells). It forms a complex with the ferric atom in this enzyme. The binding of cyanide ions to this cytochrome prevents electrons from being transferred from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted, and the cell can no longer perform aerobic respiration to produce ATP for energy. Tissues that rely primarily on aerobic respiration, such as the central nervous system and the heart, are particularly susceptible to this. Cyanide can also produce some toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydrocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinate dehydrogenase, and copper/zinc superoxide dismutase. Cyanide binds to the iron ions in methemoglobin to form inactive methemoglobin cyanide. (L97) Prunasin is a cyanogenic glycoside and can release hydrogen cyanide, a toxic compound. The compound's toxicity is primarily related to its cyanogenic potential. Standard laboratory safety precautions should be observed when handling this compound. The compound is classified as a Dangerous Good for transport. Toxicity studies would be required to determine the safety profile. |
| References | |
| Additional Infomation |
(R)-prunasin is a type of prunasin. It has been reported to be found in camellia (Camellia sinensis), oak-leaved Visconcelea (Vasconcellea quercifolia), and other organisms with relevant data. Prunasin is also found in almonds. Prunasin can be isolated from the kernels of plum plants, the immature fruits of passionflower plants, and the leaves of perilla (Perilla frutescens var. acuta). Prunasin belongs to the O-glycoside family. These compounds are glycosides in which one sugar group is linked to another sugar group via an O-glycosidic bond through a carbon atom.
Prunasin is a research-grade natural product supplied for DNA repair and cancer research. It is not an approved pharmaceutical and has no clinical trial history. The compound is a naturally occurring cyanogenic glycoside and an inhibitor of DNA polymerase β. It is the main metabolite of Amygdalin. This product is intended for research use only. |
| Molecular Formula |
C14H17NO6
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|---|---|
| Molecular Weight |
295.29
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| Exact Mass |
295.105
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| CAS # |
99-18-3
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| PubChem CID |
119033
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
527.0±50.0 °C at 760 mmHg
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| Melting Point |
138-148ºC
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| Flash Point |
272.5±30.1 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.621
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| LogP |
-0.92
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
21
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| Complexity |
377
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| Defined Atom Stereocenter Count |
6
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| SMILES |
C1=CC=C(C=C1)[C@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
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| InChi Key |
ZKSZEJFBGODIJW-GMDXDWKASA-N
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| InChi Code |
InChI=1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9-,10+,11+,12-,13+,14+/m0/s1
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| Chemical Name |
(2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
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| Synonyms |
Prunasin
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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) |
H2O : ≥ 50 mg/mL (~169.33 mM)
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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 | 3.3865 mL | 16.9325 mL | 33.8650 mL | |
| 5 mM | 0.6773 mL | 3.3865 mL | 6.7730 mL | |
| 10 mM | 0.3387 mL | 1.6933 mL | 3.3865 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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