| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
|
||
| 25mg |
|
||
| 50mg |
|
||
| 100mg |
|
||
| 250mg |
|
||
| Other Sizes |
| Targets |
Scopolin's primary biological target is Sirtuin, a class of proteins that possess histone deacetylase activity and play a role in cellular regulation, aging, and inflammation. By modulating Sirtuin activity, scopolin influences the Cell Cycle/DNA Damage and Epigenetics pathways. Additionally, scopolin has been shown to reduce the production of key inflammatory mediators such as PGE2 and LTC4, suggesting it may also interact with or modulate the arachidonic acid pathway. This dual action on epigenetic regulators and inflammatory mediators positions scopolin as a compound of interest for studying inflammation and related diseases.
|
|---|---|
| ln Vitro |
In HepG2 cells, scopin (100 μM, 24 hours) prevents base buildup brought on by oleic acid by raising SIRT1 activity [2]. The pre-osteoclast RAW 264.7 cells' ability to secrete osteoclasts generated by RANKL is inhibited by Scopolin (10 μM, 5 days) [5].
In vitro, scopolin has demonstrated anti-inflammatory activity by reducing the production of prostaglandin E2 (PGE2) and leukotriene C4 (LTC4). These are key lipid mediators involved in the inflammatory response. The exact cellular mechanisms are not fully detailed, but the reduction in these mediators suggests that scopolin may inhibit the activity of enzymes such as cyclooxygenase (COX) and lipoxygenase (LOX), or it may act upstream to modulate the signaling pathways that lead to their production. As a Sirtuin modulator, it may also influence gene expression related to inflammation. |
| ln Vivo |
In HFD-fed infants, scopicon (0.02% (w/w) in the diet for 8 weeks) decreases myocardial steatosis and reduces weight gain [2]. Extracellular choline in stored brain increases to about 300% when scopolin (2 μmol, icv) is added [3]. By inhibiting both angiogenesis and adjuvant, scopolamine (50, 100 mg/kg, intraperitoneal injection) prevents adjuvant-induced arthritis [4].
In vivo, scopolin has been shown to have metabolic effects. In mice fed a high-fat diet (HFD), administration of scopolin at 0.02% (w/w) in the diet for 8 weeks decreased body weight gain and alleviated hepatic steatosis (fatty liver). This suggests that scopolin may have beneficial effects on metabolism and could be useful in studying obesity and non-alcoholic fatty liver disease (NAFLD). Additionally, intracerebroventricular (icv) administration of scopolin at 2 μmol in rats increased the extracellular acetylcholine concentration in the brain to about 300% of basal release. This indicates that scopolin can modulate cholinergic neurotransmission, potentially by inhibiting acetylcholinesterase or by promoting acetylcholine release. |
| Enzyme Assay |
Non-cellular in vitro assays for scopolin involve studying its anti-inflammatory activity in cell-free systems. For example, the compound's ability to inhibit the production of PGE2 and LTC4 can be assessed using enzyme assays. Recombinant enzymes such as COX-1, COX-2, or 5-LOX are incubated with their respective substrates (arachidonic acid) in the presence or absence of scopolin. The production of PGE2 or LTC4 is then measured using ELISA or LC-MS. The IC50 value for inhibition of these enzymes can be calculated. Alternatively, the compound's antioxidant capacity can be measured using assays such as DPPH radical scavenging or ABTS assays, where the reduction in absorbance is measured spectrophotometrically.
|
| Cell Assay |
Cellular assays for scopolin are typically performed using immune cells such as macrophages or microglia. Cells are pre-treated with scopolin at various concentrations for 1-2 hours and then stimulated with an inflammatory stimulus such as lipopolysaccharide (LPS). After stimulation, the culture media is collected, and the levels of PGE2 and LTC4 are measured by ELISA. Additionally, the expression of inflammatory genes (e.g., COX-2, TNF-α, IL-1β) can be assessed by RT-PCR. Cell viability is also measured using an MTT assay to ensure that the observed effects are not due to cytotoxicity.
|
| Animal Protocol |
Animal/Disease Models: HFD-fed C57BL/6 N mice [2]
Doses: 0.02% (w/w) HFD in diet (equivalent to 20 mg/kg body weight) Route of Administration: Supplementation in diet, 8 weeks Experimental Results: Reversal HFD-induced hepatic TG, cholesterol, and fatty acid accumulation increased by 35%, 49%, and 35%, respectively. Reversed the HFD-induced decrease in plasma adiponectin levels by 76% and diminished elevated plasma MCP-1, TNFα, and IL-6 levels. The HFD-induced downregulation of SIRT1 activity was restored. Animal/Disease Models: Adjuvant-induced arthritis (AIA) rats [4] Doses: 50, 100 mg/kg Route of Administration: intraperitoneal (ip) injection Experimental Results: Inhibition of swelling and joint index scores in vaccinated and unvaccinated paws. Reduce new blood vessels and reduce the expression of IL-6, VEGF and FGF-2 in rat synovial tissue. In vivo animal studies for scopolin have been conducted in mouse models of diet-induced obesity and rat models for neurological effects. For the metabolic study, mice are fed a high-fat diet (HFD) with or without 0.02% (w/w) scopolin for 8 weeks. Body weight and food intake are monitored weekly. At the end of the study, blood samples are collected for analysis of glucose, insulin, and lipid profiles. Liver tissues are harvested for histological examination (H&E and Oil Red O staining) to assess steatosis. For the neurological study, rats receive an intracerebroventricular (icv) injection of scopolin (2 μmol), and brain microdialysis is used to measure extracellular acetylcholine levels. |
| ADME/Pharmacokinetics |
Scopolin is a small molecule glucoside with moderate water solubility and is soluble in DMSO. Its pharmacokinetic properties are not fully characterized, but as a glucoside, it may be hydrolyzed by β-glucosidases in the intestine to release its aglycone, scopoletin, which is more lipophilic and likely the active form. The absorption, distribution, metabolism, and excretion (ADME) of scopolin are expected to be influenced by its sugar moiety. For in vivo studies, scopolin is often administered orally in the diet. The metabolic effects observed in the HFD-fed mice suggest that it is bioavailable and can reach sufficient concentrations in the liver to exert its effects.
|
| Toxicity/Toxicokinetics |
Scopolin is a naturally occurring compound and is generally considered to have low toxicity. In the mouse study where it was administered at 0.02% (w/w) in the diet for 8 weeks, no overt signs of toxicity were reported. However, comprehensive toxicological data are limited. As a research compound, it should be handled with standard laboratory precautions. It is not a clinically approved drug and is used only for research purposes. Its safety profile in humans has not been established.
|
| References |
|
| Additional Infomation |
Scopolamine is a coumarin compound consisting of scopolamine linked to the 7-position of a β-D-glucopyranose residue via a glycosidic bond. It is a plant metabolite. It is a monosaccharide derivative belonging to the coumarin class and is also a β-D-glucoside. Its function is related to that of scopolamine. Scopolamine has been reported in Erycibe obtusifolia, Mandragora autumnalis, and other organisms with relevant data. See also: Flower (part) of Chamaemelum nobile.
Scopolin is a secondary metabolite found in plants such as Scopolia carniolica, Scopolia japonica, and Scopolia lurida. It is the glucoside of scopoletin, a well-known coumarin with various biological activities. The compound is of interest in the fields of natural product chemistry, pharmacology, and nutrition. Its ability to modulate Sirtuin activity and reduce inflammation makes it a candidate for studying age-related diseases and metabolic disorders. Scopolin is not approved for clinical use and is not in clinical trials. It is primarily a research tool for understanding the biological activities of coumarin glucosides. |
| Molecular Formula |
C16H18O9
|
|---|---|
| Molecular Weight |
354.31
|
| Exact Mass |
354.095
|
| CAS # |
531-44-2
|
| PubChem CID |
439514
|
| Appearance |
White to off-white solid powder
|
| Density |
1.6±0.1 g/cm3
|
| Boiling Point |
650.2±55.0 °C at 760 mmHg
|
| Melting Point |
217ºC
|
| Flash Point |
241.5±25.0 °C
|
| Vapour Pressure |
0.0±2.0 mmHg at 25°C
|
| Index of Refraction |
1.639
|
| LogP |
-1.87
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
9
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
25
|
| Complexity |
510
|
| Defined Atom Stereocenter Count |
5
|
| SMILES |
O1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])O[H])O[H])O[H])O[H])OC1C([H])=C2C(C([H])=C([H])C(=O)O2)=C([H])C=1OC([H])([H])[H]
|
| InChi Key |
SGTCGCCQZOUMJJ-YMILTQATSA-N
|
| InChi Code |
InChI=1S/C16H18O9/c1-22-9-4-7-2-3-12(18)23-8(7)5-10(9)24-16-15(21)14(20)13(19)11(6-17)25-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1
|
| Chemical Name |
6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
|
| Synonyms |
Scopolin ScopolosideMurrayin NSC404560 NSC-404560NSC 404560
|
| 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: 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)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~282.24 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.06 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.06 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.06 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8224 mL | 14.1119 mL | 28.2239 mL | |
| 5 mM | 0.5645 mL | 2.8224 mL | 5.6448 mL | |
| 10 mM | 0.2822 mL | 1.4112 mL | 2.8224 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.
|
|
|
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
