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Damnacanthal, a naturally occuring anthraquinone isolated from the root of Morinda citrifolia, is a novel and potent inhibitor of p56lck tyrosine kinase and is able to mobilizes intracellular Ca2+ in dermal fibroblasts and inhibits Ras function.
| ln Vitro |
When it comes to p56lck, damnacanthal is >40-fold selective over four receptor tyrosine kinases and >100-fold selective over serine/threonine kinase, protein kinase A, and protein kinase C. A modest (7–20-fold) but very statistically significant selectivity for p56lck over the homologous enzymes p60src and p59fyn is also demonstrated by damnacanthal [1]. Treatment with damnacanthal (0.1-100 μM; 1-4 days) significantly reduces cell proliferation in HCT-116 and SW480 cells in a way that is dependent on both concentration and time [2]. At a concentration of 50 μM, damnacanthal (1-50 μM; 72 hours; HCT-116 cells) treatment led to a considerable enrichment of S/G1 and G2/G1 phase cell numbers [2]. Treatment with damnacanthal (10 μM) for 24 hours dramatically boosted the activity of caspase 3/7 in HCT-116 cells. Apoptosis is induced by damnacanthal[2]. NAG-1 expression is induced in HCT-116 cells by damnacanthal treatment (0.1–10 μM; 24 hours). The expression of p21 and p53 remained unchanged at 10 μM Damnacanthal, while that of cyclin D1 was decreased. Only HCT-116 cells that are treated with 10 μM Damnacanthal induce PARP cleavage [2]. After two weeks of treatment with damnacanthal, the number of colonies in HCT-116 cells significantly decreased in a concentration-dependent manner. The clonogenic potential of cells treated with damnacanthal was significantly inhibited. The migration of HCT-116 cells was dramatically reduced in a concentration-dependent manner by cells treated with damnacanthal (1-50 μM) for 48 hours [2].
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| ln Vivo |
Damnacanthal (10-100 mg/kg; p.o.; 10-300 min; male ddY mice) therapy revealed considerable analgesia in a dose-dependent manner in the formalin assay. Administration of damnacanthal (100 mg/kg) effectively reduced histamine-induced paw edema [4].
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| Cell Assay |
Cell Proliferation Assay[2]
Cell Types: HCT-116 and SW480 Cell Tested Concentrations: 0.1 μM, 1 μM, 10 μM, 100 μM Incubation Duration: 1, 2 and 4 Days Experimental Results: Result in significant reduction in cell proliferation concentration and time dependent Way. Cell cycle analysis [2] Cell Types: HCT-116 Cell Tested Concentrations: 1 μM, 10 μM and 50 μM Incubation Duration: 72 hrs (hours) Experimental Results: The concentration of 50 μM resulted in significant enrichment of cell numbers in S/G1 and G2/G1 phases. Apoptosis analysis[2] Cell Types: HCT-116 Cell Tested Concentrations: 10 μM Incubation Duration: 24 hrs (hours) Experimental Results: Significant increase in caspase 3/7 activity. Western Blot Analysis[2] Cell Types: HCT-116 Cell Tested Concentrations: 0.1 μM, 1 μM and 10 μM Incubation Duration: 24 hrs (hours) Experimental Results: NAG-1 was induced in HCT-116 cells in a dose- and time-dependent manner. Cyclin D1 expression diminished at 10 μM. |
| Animal Protocol |
Animal/Disease Models: Male ddY mice (5-6 weeks) are injected with formalin or histamine [4]
Doses: 10 mg/kg, 30 mg/kg and 100 mg/kg Route of Administration: oral; injection; Administration by injection. Results at 10, 30, 60 or 300 minutes: Significant reduction in human lung tumor growth without acute toxicity. |
| References |
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| Additional Infomation |
3-hydroxy-1-methoxy-9,10-dioxo-2-anthracenecarboxaldehyde is a monohydroxyanthraquinone and an aldehyde.
Damnacanthal has been reported in Damnacanthus indicus, Damnacanthus major, and other organisms with data available. Damnacanthal is an alkaloid phytochemical found in the Morinda Citrifolia (Noni) that inhibits the growth of RAS cancer cells. The exact mechanism is unknown but may involve the inhibition of tyrosine kinase. (NCI) |
| Molecular Formula |
C16H10O5
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|---|---|
| Molecular Weight |
282.2476
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| Exact Mass |
282.052
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| CAS # |
477-84-9
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| PubChem CID |
2948
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
531.9±50.0 °C at 760 mmHg
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| Flash Point |
204.9±23.6 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.692
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| LogP |
3.74
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
21
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| Complexity |
460
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
IPDMWUNUULAXLU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C16H10O5/c1-21-16-11(7-17)12(18)6-10-13(16)15(20)9-5-3-2-4-8(9)14(10)19/h2-7,18H,1H3
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| Chemical Name |
3-hydroxy-1-methoxy-9,10-dioxoanthracene-2-carbaldehyde
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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 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)
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| Solubility (In Vitro) |
DMSO : ~5 mg/mL (~17.71 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 4 mg/mL (14.17 mM) in 50% PEG300 + 50% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 4 mg/mL (14.17 mM) in 0.5% CMC-Na/saline water (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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 | 3.5430 mL | 17.7148 mL | 35.4296 mL | |
| 5 mM | 0.7086 mL | 3.5430 mL | 7.0859 mL | |
| 10 mM | 0.3543 mL | 1.7715 mL | 3.5430 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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