| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| 50mg |
|
||
| Other Sizes |
| Targets |
9-Methoxycanthin-6-one targets several pathways. It inhibits topoisomerases I and II, leading to DNA damage and apoptosis. It also inhibits NF-κB and reduces inflammatory cytokine production. Additionally, it shows activity against Plasmodium falciparum by inhibiting hemozoin formation. It also induces cell cycle arrest at G2/M phase in cancer cells.
|
|---|---|
| ln Vitro |
9-Methoxycanthin-6-one was separated, concentrating on the taproot and fibrous roots, from Tongkat Ali Jack explants (Eurycoma longifolia Jack) [1].
In vitro, 9-methoxycanthin-6-one shows potent cytotoxicity against various cancer cell lines, including HeLa (IC50 ~ 2 µM), MCF-7 (IC50 ~ 3 µM), and A549 (IC50 ~ 4 µM) after 48 h. It also inhibits the growth of P. falciparum with an IC50 of 0.5 µM. It reduces LPS-induced NO in macrophages with an IC50 of 5 µM. |
| ln Vivo |
In vivo, the compound has shown anti-tumor activity in mouse xenografts. In HeLa tumor-bearing mice, intraperitoneal administration of 10 mg/kg every other day for 14 days reduced tumor growth by 60%. In a mouse model of malaria (P. berghei), oral administration of 20 mg/kg for 4 days reduced parasitemia by 70%. It also showed anti-inflammatory effects in a carrageenan paw edema model.
|
| Enzyme Assay |
The in vitro topoisomerase inhibition assay is performed using a DNA relaxation assay. Human topoisomerase I or II is incubated with supercoiled pBR322 DNA and 9-methoxycanthin-6-one (0.1-10 µM) for 30 min at 37°C. The reaction products are analyzed by agarose gel electrophoresis. The IC50 is determined. For anti-malarial, the compound is tested against P. falciparum in culture, and parasite growth is measured by [³H]hypoxanthine incorporation.
|
| Cell Assay |
For in vitro cell-based assays, cancer cells are seeded in 96-well plates and treated with the compound (0.1-10 µM) for 48 h. Cell viability is assessed by MTT. Cell cycle analysis is performed by propidium iodide staining and flow cytometry. Apoptosis is evaluated by annexin V/PI staining and caspase-3 activity.
|
| Animal Protocol |
In vivo xenograft studies in BALB/c nude mice: mice are inoculated subcutaneously with HeLa cells. When tumors reach ~100 mm³, the compound is administered i.p. at 5, 10, 20 mg/kg every other day for 14 days. Tumor volumes are measured. For anti-malarial studies, mice infected with P. berghei are treated orally, and parasitemia is monitored by blood smears.
|
| ADME/Pharmacokinetics |
Pharmacokinetic data are limited. In rats after i.v. administration (5 mg/kg), half-life is 2 h, and volume of distribution is 1 L/kg. Oral bioavailability is ~15%. The compound is metabolized by CYP450 and excreted in bile and urine. Plasma protein binding is ~70%.
|
| Toxicity/Toxicokinetics |
The compound has moderate toxicity (LD50 ~ 50 mg/kg, i.p. in mice). Oral LD50 is ~200 mg/kg. At therapeutic doses (5-10 mg/kg), no major toxicity is observed. High doses cause weight loss and hepatotoxicity. It is not mutagenic in the Ames test.
|
| References | |
| Additional Infomation |
9-Methoxycansin-6-one is an indole alkaloid, a 9-methoxy derivative of cansin-6-one. It was isolated from Eurycoma longifolia and Simaba multiflora, and exhibits cytotoxic activity against human cancer cell lines. It can be used as a metabolite, an antitumor drug, and an antimalarial drug. It is an indole alkaloid, aromatic ether, and organic heterotetracyclic compound functionally related to cansin-6-one. 9-Methoxycansin-6-one has been reported to exist in Simaba orinocensis, Simaba glauca, and other organisms with relevant data.
9-Methoxycanthin-6-one is a promising natural product with antimalarial and anticancer activities. It has been studied for its topoisomerase inhibition. However, its toxicity and poor bioavailability limit development. No clinical trials have been reported. It is used as a research tool. |
| Molecular Formula |
C₁₅H₁₀N₂O₂
|
|---|---|
| Molecular Weight |
250.25
|
| Exact Mass |
250.074
|
| CAS # |
74991-91-6
|
| PubChem CID |
9881423
|
| Appearance |
Light yellow to yellow solid powder
|
| LogP |
2.447
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
19
|
| Complexity |
422
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
OWCRARVHWCCRAG-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C15H10N2O2/c1-19-9-2-3-10-11-6-7-16-12-4-5-14(18)17(15(11)12)13(10)8-9/h2-8H,1H3
|
| Chemical Name |
13-methoxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
|
| Synonyms |
9Methoxycanthin6one; 9 Methoxycanthin 6 one
|
| 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 |
| 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 : ~12.5 mg/mL (~49.95 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (5.00 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 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 12.5 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9960 mL | 19.9800 mL | 39.9600 mL | |
| 5 mM | 0.7992 mL | 3.9960 mL | 7.9920 mL | |
| 10 mM | 0.3996 mL | 1.9980 mL | 3.9960 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
