| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 100mg |
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| 250mg | |||
| Other Sizes |
| Targets |
20-Deoxyingenol primarily targets transcription factor EB (TFEB), a master regulator of autophagy and lysosomal function. By facilitating the nuclear translocation of TFEB, the compound activates autophagy and lysosomal biogenesis pathways. This mechanism promotes the clearance of damaged cellular components and maintains cellular homeostasis. The compound's ability to induce autophagy through TFEB activation makes it a valuable tool for studying autophagy-related processes and potential therapeutic applications in conditions such as osteoarthritis and other autophagy-related diseases.
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| ln Vitro |
20-Deoxyingenol (2.5-10 mM; 24 hours) protects chondrocytes from cell death induced by tert-butyl hydroperoxide solution (TBHP; 100 μM) [2]. 20-Deoxyingenol (5-10 mM) can reduce the TBHP-induced upregulation of the apoptotic protein cleaved-caspase3 and the senescence protein p16INK4a in chondrocytes [2]. At concentrations below 10 mM, 20-Deoxyingenol (2.5–40 mM; 24 h) has no cytotoxic effect on chondrocytes [2]. In chondrocytes treated with TBHP, 20-Deoxyingenol (10 mM) restores autophagic flux over a 24-hour period [2]. 20-Deoxyingenol (4-10 mM; 24 hours) promotes nuclear levels of TFEB in TBHP-treated chondrocytes [2].
In vitro, 20-Deoxyingenol (2.5-10 mM; 24 h) protects chondrocytes against tert-butyl hydroperoxide solution (TBHP)-induced oxidative damage. The compound promotes autophagy and lysosomal biogenesis by promoting nuclear translocation of TFEB in vitro. It shows antiviral activity against HIV-1 NL4-3 infected human MT4 cells with an EC50 greater than 12000.0 nM and exhibits cytotoxicity against MT4 cells with a CC50 greater than 12000.0 nM. The compound demonstrates antioxidant and osteoprotective activities in cell-based assays. |
| ln Vivo |
In a mouse DMM model, 20-Deoxyingenol (20 mg/kg/d; intraperitoneal injection for 8 weeks) can slow the advancement of OA [2].
In vivo, 20-Deoxyingenol (20 mg/kg per day, i.p.) reduces bone erosion and cartilage calcification in joints in a mouse model of injury-induced osteoarthritis. The compound's ability to induce autophagy through TFEB activation has been demonstrated in animal models. Its anti-osteoarthritic effects have been evaluated in preclinical studies. The compound is typically administered via intraperitoneal injection in animal studies. Further in vivo studies are ongoing to fully characterize its therapeutic potential for osteoarthritis and other autophagy-related conditions. |
| Enzyme Assay |
In vitro enzyme/receptor binding assays for 20-Deoxyingenol involve measuring TFEB nuclear translocation and autophagy activation. Cells are treated with the compound at varying concentrations (2.5-10 mM) and TFEB localization is assessed by immunofluorescence microscopy or cellular fractionation followed by Western blot. Autophagy markers such as LC3-II conversion and p62 degradation are measured by Western blot. Lysosomal biogenesis is evaluated by assessing lysosomal-associated membrane protein levels. Assays are performed in appropriate cell culture systems with positive controls such as known autophagy inducers (e.g., rapamycin). IC50 values for antiviral activity are calculated from dose-response curves.
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| Cell Assay |
In vitro cell-based assays for 20-Deoxyingenol are conducted in chondrocytes, MT4 cells, and other relevant cell lines. Cells are cultured in appropriate media at 37°C with 5% CO2 and treated with the compound at varying concentrations (e.g., 2.5-10 mM for 24 hours). Cell viability is assessed by MTT or CCK-8 assays. Autophagy is evaluated by monitoring LC3-II puncta formation, autophagosome accumulation, and lysosomal biogenesis. For antiviral studies, MT4 cells are infected with HIV-1 NL4-3 and viral replication is measured. Cytotoxicity is assessed to determine CC50 values. Experiments are performed in triplicate with appropriate positive and negative controls.
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| Animal Protocol |
Animal/Disease Models: 10weeks old C57BL/6 male wild-type (WT) mice with unstable medial meniscus (DMM) [2]
Doses: 20 mg/kg Route of Administration: intraperitoneal (ip) injection, one time/day, results for eight consecutive weeks Experimental Results: Compared with the DMM group, the joint space was slightly wider and bone density and calcification were diminished. Inhibits the reduction of hyaline cartilage (HC) thickness and reduces the disorder and hypertrophy of chondrocytes in mouse joint tissue after DMM surgery. The surface of articular cartilage is less eroded and contains more proteoglycans. There are more positive staining spots for LAMP1 and LC3 II, and fewer positive staining spots for cleaved-caspase3 and P16INK4a. Increased nuclear levels of TFEB. In vivo animal studies for 20-Deoxyingenol are conducted in mouse models of injury-induced osteoarthritis. Mice are treated with 20-Deoxyingenol at 20 mg/kg per day via intraperitoneal injection. Disease progression is monitored by assessing bone erosion and cartilage calcification in joints using micro-CT imaging and histological analysis. For antiviral studies, animal models of HIV infection may be used. Dosing regimens are optimized based on pharmacokinetic data. Animals are monitored for clinical signs. Tissues and blood samples are collected for histopathological and biomarker analysis at study endpoints. Studies are conducted in accordance with institutional animal care guidelines. |
| ADME/Pharmacokinetics |
20-Deoxyingenol (MW 332.43 g/mol, C20H28O4) is a diterpene with favorable solubility properties. It is soluble in DMSO (49 mg/mL, 147.4 mM) and can be formulated for in vivo administration in 10% DMSO + 90% Corn Oil (2.5 mg/mL, 7.52 mM). The compound is stable as a powder at -20°C for up to 3 years and in solvent at -80°C for 1 year. Pharmacokinetic parameters such as Cmax, Tmax, and half-life would be determined in species-specific studies. The compound is typically administered via intraperitoneal injection in preclinical studies.
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| Toxicity/Toxicokinetics |
20-Deoxyingenol is generally well-tolerated in preclinical studies at therapeutic doses. The compound is a natural diterpene derived from Euphorbia kansui. In vitro studies show a CC50 greater than 12000.0 nM in MT4 cells, indicating a favorable safety margin with a selectivity index greater than 10.0 for antiviral activity. No significant adverse effects have been reported in the available literature at research-use concentrations. The compound is intended for research use only. Standard safety precautions should be followed when handling. Comprehensive toxicological evaluation would be required for therapeutic development.
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| References | |
| Additional Infomation |
It has been reported that plants in the genera Euphorbia (peplus) and Euphorbia segetalis contain 20-deoxyingerm alcohol, and relevant data are available for reference.
20-Deoxyingenol is a diterpene derived from Euphorbia kansui that promotes autophagy and lysosomal biogenesis through TFEB nuclear translocation. It exhibits antiviral activity against HIV-1 with an EC50 greater than 12000.0 nM and shows antioxidant and osteoprotective properties. The compound is being researched for osteoarthritis and other autophagy-related conditions. Its mechanism of action involves TFEB activation, making it a valuable tool for studying autophagy regulation. All applications are limited to non-human research use. |
| Molecular Formula |
C20H28O4
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|---|---|
| Molecular Weight |
332.4
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| Exact Mass |
332.198
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| CAS # |
54706-99-9
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| PubChem CID |
11290503
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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 |
470.5±45.0 °C at 760 mmHg
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| Flash Point |
252.4±25.2 °C
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| Vapour Pressure |
0.0±2.6 mmHg at 25°C
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| Index of Refraction |
1.605
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| LogP |
3.51
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
24
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| Complexity |
690
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| Defined Atom Stereocenter Count |
8
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| SMILES |
C[C@@H]1C[C@@H]2[C@@H](C2(C)C)[C@@H]3C=C([C@H]([C@]4([C@@]1(C3=O)C=C([C@@H]4O)C)O)O)C
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| InChi Key |
FOSYZKSOJUQLTD-NHPMXQBPSA-N
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| InChi Code |
InChI=1S/C20H28O4/c1-9-6-12-14-13(18(14,4)5)7-11(3)19(17(12)23)8-10(2)16(22)20(19,24)15(9)21/h6,8,11-16,21-22,24H,7H2,1-5H3/t11-,12+,13-,14+,15-,16+,19+,20+/m1/s1
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| Chemical Name |
(1S,4S,5S,6R,9S,10R,12R,14R)-4,5,6-trihydroxy-3,7,11,11,14-pentamethyltetracyclo[7.5.1.01,5.010,12]pentadeca-2,7-dien-15-one
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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 |
| 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) |
DMSO : ~50 mg/mL (~150.41 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (7.52 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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 (7.52 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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 (7.52 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 | 3.0084 mL | 15.0421 mL | 30.0842 mL | |
| 5 mM | 0.6017 mL | 3.0084 mL | 6.0168 mL | |
| 10 mM | 0.3008 mL | 1.5042 mL | 3.0084 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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