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| Targets |
Ailanthone is a potent inhibitor of both the full-length androgen receptor (AR) and constitutively active truncated AR splice variants. It inhibits the intact AR with an IC50 of 69 nM and the AR1-651 variant with an IC50 of 309 nM. Its mechanism involves disrupting the AR-chaperone complex by binding p23 and blocking AR interaction with HSP90, causing ubiquitin-proteasome system (UPS) degradation of AR. It also triggers DNA damage characterized by activation of the ATM/ATR pathway and induces apoptosis which is mitochondrion-mediated and involves the PI3K/AKT signaling pathway.
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| ln Vitro |
Ailanthon is a strong reaction to constitutively active truncated AR splice variants (AR-Vs) and full-length AR (AR-FL). In order to disrupt the AR-participant complex and further ubiquitin/proteosome-mediated degradation of AR and p23 clients, such as AKT and Cdk4, as well as Folding AR other target genes in PCa cell lines and orthotopic animal tumors, Ailanthon binds to the accessory component protein p23 and inhibits AR from responding to HSP90. Ailanthin has the ability to stop tumor growth and CRPC growth [1]. It has been demonstrated that ailanthin inhibits the growth of tumor cells in a range of cell lines, such as HepG2, Hep3B, R-HepG2, Jurkat, HeLa, MCF-7, MDA-MB-, 231, and A549 cells. Ailanthone inhibits the growth of Huh7 cells by blocking G0/G1 cell cycle candles and pathway-directed cells. Huh7 cells have mitochondria-directed Ailanthone-induced cell conduits that are mediated by PI3K/AKT signaling [2].
In vitro, Ailanthone demonstrates potent anticancer activity. It inhibits the growth of Huh7 hepatocellular carcinoma cells by blocking the G0/G1 cell cycle. It induces apoptosis, which is mitochondrion-mediated and involves the PI3K/AKT signaling pathway. It also triggers DNA damage via the ATM/ATR pathway. Its potent AR inhibition makes it a valuable tool for studying AR signaling in prostate cancer. |
| ln Vivo |
Ailanthin administered PO as well as by intraperitoneal injection is very effective in preventing the formation of CRPC xenografts. Ailanthin demonstrated good solubility and bioavailability in pharmacokinetic studies (>20). Furthermore, during the course of treatment, the concentration of the adsorbed drug did not attain a stable level; yet, ailanthin tumors were able to effectively limit the growth of CRPC [1].
In vivo, Ailanthone has been studied for its antitumor effects. Its ability to inhibit AR and induce apoptosis suggests it has significant therapeutic potential for treating prostate cancer and other cancers. However, specific in vivo efficacy data are not extensively documented. Further studies are needed to confirm its therapeutic potential. |
| Enzyme Assay |
For in vitro receptor binding and enzyme assays, the activity of Ailanthone can be assessed. For AR binding, a radioligand binding assay using a labeled AR ligand can be performed. For its effect on the AR-chaperone complex, immunoprecipitation and Western blotting can be used to study the interaction between AR, p23, and HSP90. For its effects on cell cycle and apoptosis, flow cytometry and caspase activity assays can be used.
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| Cell Assay |
For in vitro cell-based assays, the anticancer activity of Ailanthone is evaluated using various cancer cell lines, including Huh7 and AR-positive prostate cancer cell lines. Cells are treated with the compound, and cell viability is measured using MTT or CCK-8 assays. Apoptosis is assessed by Annexin V staining. Cell cycle distribution is analyzed by flow cytometry. AR protein levels and signaling are studied by Western blotting.
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| Animal Protocol |
For in vivo animal studies, Ailanthone is typically administered orally or intraperitoneally in rodent models of cancer. Xenograft models of prostate cancer or hepatocellular carcinoma can be used. Tumor-bearing mice are treated with the compound, and tumor growth and AR signaling are monitored.
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| ADME/Pharmacokinetics |
Ailanthone has a molecular weight of 376.40. As a quassinoid, it is expected to have poor oral bioavailability. Detailed pharmacokinetic parameters are not publicly available.
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| Toxicity/Toxicokinetics |
Specific toxicity data for Ailanthone are limited. As a potent compound, it may have off-target effects. Comprehensive toxicological studies have not been published. The compound is used for research purposes only and is not intended for human use.
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| References | |
| Additional Infomation |
Ailanthone is a triterpenoid compound.
Ailanthone is a research compound with no clinical trial or regulatory approval status. It is a natural product with potent anticancer activity, particularly as an AR inhibitor. It is commercially available from chemical suppliers for research purposes only. |
| Molecular Formula |
C₂₀H₂₄O₇
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|---|---|
| Molecular Weight |
376.40
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| Exact Mass |
376.152
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| CAS # |
981-15-7
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| PubChem CID |
72965
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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 |
641.0±55.0 °C at 760 mmHg
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| Flash Point |
231.6±25.0 °C
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| Vapour Pressure |
0.0±4.3 mmHg at 25°C
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| Index of Refraction |
1.640
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| LogP |
-0.76
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
27
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| Complexity |
817
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| Defined Atom Stereocenter Count |
9
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| SMILES |
CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@]([C@@H](C(=C)[C@@H]4CC(=O)O3)O)(OC5)O)C)O
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| InChi Key |
WBBVXGHSWZIJST-RLQYZCPESA-N
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| InChi Code |
InChI=1S/C20H24O7/c1-8-4-12(21)16(24)18(3)10(8)5-13-19-7-26-20(25,17(18)19)15(23)9(2)11(19)6-14(22)27-13/h4,10-11,13,15-17,23-25H,2,5-7H2,1,3H3/t10-,11-,13+,15+,16+,17+,18+,19+,20-/m0/s1
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| Chemical Name |
(1R,2R,3aS,3a1S,6aR,7aS,11S,11aS,11bR)-1,2,11-trihydroxy-8,11a-dimethyl-3-methylene-1,2,3,3a,4,7,7a,11,11a,11b-decahydro-5H-1,3a1-(epoxymethano)dibenzo[de,g]chromene-5,10(6aH)-dione
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| Synonyms |
Ailanthone Δ13-Dehydrochaparrinone
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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 (~132.84 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.53 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 20.8 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: ≥ 2.08 mg/mL (5.53 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 20.8 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: ≥ 2.08 mg/mL (5.53 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 | 2.6567 mL | 13.2837 mL | 26.5675 mL | |
| 5 mM | 0.5313 mL | 2.6567 mL | 5.3135 mL | |
| 10 mM | 0.2657 mL | 1.3284 mL | 2.6567 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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