| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
|
||
| 100mg | |||
| Other Sizes |
| Targets |
8-O-Acetylharpagide targets the Drosophila ecdysteroid receptor, where it functions as a nonsteroidal agonist. In receptor binding assays, the compound competes with tritiated-ponasterone A for binding to the Drosophila ecdysteroid receptor. It also targets anti-aging and anti-cancer pathways; at low doses it demonstrates significant anti-aging properties, while high doses induce apoptosis and necrosis in cancer cells by downregulating anti-apoptotic proteins such as Akt, p-Akt, and Bcl-2. Additionally, the compound shows activity against NF-kappaB activation and has biological activity on isolated smooth muscle preparations.
|
|---|---|
| ln Vitro |
In vitro studies have demonstrated that 8-O-Acetylharpagide exhibits an EC50 of 22 microM as an ecdysteroid agonist. It selectively induces G2/M phase arrest and radiosensitivity in hypopharyngeal cancer cells, with an IC50 of 0.88 mM on FaDu cells and 1.65 mM on PDL cells, yielding a selectivity index of approximately 1.85. The compound also shows antiplasmodial activity and exhibits antitumoral, antiviral, antibacterial, and anti-inflammatory effects in various in vitro assays. It inhibits Epstein-Barr virus (EBV) infection and shows inhibitory effects on two-stage carcinogenesis tests.
|
| ln Vivo |
In vivo studies have demonstrated that 8-O-Acetylharpagide exhibits remarkable inhibitory effects on two-stage carcinogenesis tests of mouse skin tumors and hepatic tumors. The compound also shows anti-inflammatory activity in various animal models. As an iridoid glycoside prodrug, it is metabolized in vivo to harpagide, which is the active metabolite responsible for its pharmacological effects. The compound has also been shown to have biological activity on isolated smooth muscle preparations from guinea pig, indicating potential effects on smooth muscle function in vivo.
|
| Enzyme Assay |
The in vitro receptor binding assays for 8-O-Acetylharpagide typically involve measuring its affinity for the Drosophila ecdysteroid receptor using radioligand binding techniques. In these assays, the compound competes with tritiated-ponasterone A for binding to the receptor. Membrane preparations containing the receptor are incubated with the radiolabeled ligand and varying concentrations of 8-O-Acetylharpagide. Nonspecific binding is determined in the presence of excess unlabeled ligand. The compound's EC50 for receptor activation is determined using ecdysteroid response element reporter assays. These assays are standard for characterizing the compound's activity as an ecdysteroid agonist.
|
| Cell Assay |
Cellular assays for 8-O-Acetylharpagide are conducted using various cancer cell lines, including FaDu hypopharyngeal cancer cells and PDL cells. Cells are cultured in appropriate media and treated with varying concentrations of the compound for specified time periods. Cell viability is assessed using standard assays such as MTT or CCK-8, and IC50 values are calculated from dose-response curves. For mechanistic studies, cells are analyzed for cell cycle distribution, apoptosis markers, and signaling pathway proteins such as Akt, p-Akt, and Bcl-2 using flow cytometry and Western blotting. These assays confirm the compound's anticancer activity and provide insights into its mechanism of action.
|
| Animal Protocol |
In vivo animal studies for 8-O-Acetylharpagide have been conducted in mouse models of two-stage skin carcinogenesis and hepatic tumorigenesis. In these studies, mice are treated with the compound at various doses, and tumor development is monitored. The compound's inhibitory effects on tumor formation are assessed by measuring tumor incidence, multiplicity, and size. Anti-inflammatory activity has been studied in animal models of inflammation. The compound's metabolism to harpagide has also been studied in vivo to characterize its pharmacokinetic profile and first-pass metabolism.
|
| ADME/Pharmacokinetics |
Pharmacokinetic studies have shown that 8-O-Acetylharpagide is a prodrug that is metabolized in vivo to harpagide, providing a defined prodrug-metabolite pair essential for pharmacokinetic and first-pass metabolism studies. The compound has a molecular weight of 406.4 g/mol and a molecular formula of C17H26O11. It appears as a white to off-white solid powder. For research use, the compound is typically stored as powder at -20degC for up to 3 years or at 4degC for up to 2 years. Solubility information is available for formulation in various solvents for in vivo and in vitro studies.
|
| Toxicity/Toxicokinetics |
8-O-Acetylharpagide is a research-grade natural product with a favorable safety profile based on its traditional use in medicinal plants. As a compound isolated from plants in the Scrophulariaceae and Lamiaceae families, it has a history of use in traditional medicine with no major safety concerns reported. However, systematic toxicological evaluations of the purified compound, including acute toxicity, repeat-dose toxicity, and genotoxicity studies, would be needed to establish a comprehensive safety profile for any potential therapeutic applications. The compound is for research use only and not for human therapeutic use.
|
| References | |
| Additional Infomation |
8-O-acetylharpaside is an iridoid monoterpene compound and glycoside. It has been reported to exist in Leonurus japonicus, Betonica grandiflora, and other organisms with relevant data.
8-O-Acetylharpagide is a research-grade natural product isolated from medicinal plants such as Ajuga reptans. It is an iridoid glycoside prodrug that is metabolized in vivo to harpagide. The compound exhibits a wide range of biological activities including anti-inflammatory, analgesic, antioxidant, and antitumor properties. Its mechanism of action involves targeting ecdysteroid receptors, downregulating anti-apoptotic proteins, and inhibiting NF-kappaB activation. The compound is not approved for clinical use and is available only for research purposes in natural product chemistry, pharmacology, and drug discovery. |
| Molecular Formula |
C17H26O11
|
|---|---|
| Molecular Weight |
406.3817
|
| Exact Mass |
406.147
|
| CAS # |
6926-14-3
|
| PubChem CID |
9978650
|
| Appearance |
White to off-white solid powder
|
| Density |
1.6±0.1 g/cm3
|
| Boiling Point |
607.2±55.0 °C at 760 mmHg
|
| Melting Point |
227-229℃
|
| Flash Point |
215.9±25.0 °C
|
| Vapour Pressure |
0.0±3.9 mmHg at 25°C
|
| Index of Refraction |
1.624
|
| LogP |
-3.48
|
| Hydrogen Bond Donor Count |
6
|
| Hydrogen Bond Acceptor Count |
11
|
| Rotatable Bond Count |
5
|
| Heavy Atom Count |
28
|
| Complexity |
626
|
| Defined Atom Stereocenter Count |
10
|
| SMILES |
CC(=O)O[C@]1(C[C@H]([C@]2([C@@H]1[C@@H](OC=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)C
|
| InChi Key |
CAFTUQNGDROXEZ-XBDCZORHSA-N
|
| InChi Code |
InChI=1S/C17H26O11/c1-7(19)28-16(2)5-9(20)17(24)3-4-25-15(13(16)17)27-14-12(23)11(22)10(21)8(6-18)26-14/h3-4,8-15,18,20-24H,5-6H2,1-2H3/t8-,9-,10-,11+,12-,13-,14+,15+,16+,17-/m1/s1
|
| Chemical Name |
[(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] acetate
|
| 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 : ~25 mg/mL (~61.52 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.15 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 (6.15 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 (6.15 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 | 2.4608 mL | 12.3038 mL | 24.6075 mL | |
| 5 mM | 0.4922 mL | 2.4608 mL | 4.9215 mL | |
| 10 mM | 0.2461 mL | 1.2304 mL | 2.4608 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
