1-Methoxy-3-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde
Damnacanthal
CAS: 477-84-9
Molecular Formula: C16H10O5
1-Methoxy-3-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde - Names and Identifiers
1-Methoxy-3-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde - Physico-chemical Properties
| Molecular Formula | C16H10O5 |
| Molar Mass | 282.25 |
| Density | 1.461±0.06 g/cm3(Predicted) |
| Melting Point | 218～219℃ |
| Boling Point | 531.9±50.0 °C(Predicted) |
| Solubility | Soluble in DMSO (up to 7 mg/ml) |
| Appearance | Pale yellow |
| Color | Yellow |
| pKa | 5.26±0.20(Predicted) |
| Storage Condition | -20°C |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month. |
| In vitro study | Damnacanthal has > 100-fold selectivity for p56 lck over the serine/threonine kinases, protein kinase A and protein kinase C, and > 40-fold selectivity for p56 lck over four receptor tyrosine kinases. Damnacanthal also demonstrates modest (7-20-fold), but highly statistically significant, selectivity for p56 lck over the homologous enzymes p60 src and p59 fyn . Damnacanthal (0.1-100 μM; 1-4 days; HCT-116 and SW480 cells) treatment results in a significant reduction of cell proliferation in a concentration- and time-dependent manner. Damnacanthal (1-50 μM; 72 hours; HCT-116 cells) treatment results in a significant enrichment in the number of cells in the S/G1 and G2/G1 phases at concentration of 50 μM. Damnacanthal (10 μM; 24 hours; HCT-116 cells) treatment significantly increases caspase 3/7 activity. Damnacanthal-induced apoptosis. Damnacanthal (0.1-10 μM; 24 hours; HCT-116 cells) treatment induces NAG-1 expression in HCT-116 cells. Cyclin D1 expression is reduced at 10 μM of Damnacanthal, whereas p21 and p53 does not alter their expression. PARP cleavage is seen at 10 μM Damnacanthal treatment only in HCT-116 cells, where NAG-1 is induced. Damnacanthal treatment for 2 weeks shows significant decreasing colony number in HCT-116 cells in a concentration-dependent manner. Damnacanthal-treated cells show a dramatic inhibition of clonogenic capacity. Damnacanthal-treated (1-50 μM; 48 hours) cells significantly inhibits the migration of HCT-116 cells in a concentration-dependent manner. Cell Proliferation Assay Cell Line: HCT-116 and SW480 cells Concentration: 0.1 μM, 1 μM, 10 μM, 100 μM Incubation Time: 1, 2, and 4 days Result: Resulted in a significant reduction of cell proliferation in a concentration- and time-dependent manner. Cell Cycle Analysis Cell Line: HCT-116 cells Concentration: 1 μM, 10 μM and 50 μM Incubation Time: 72 hours Result: Resulted in a significant enrichment in the number of cells in the S/G1 and G2/G1 phases at concentration of 50 μM. Apoptosis Analysis Cell Line: HCT-116 cells Concentration: 10 μM Incubation Time: 24 hours Result: Significantly increased caspase 3/7 activity. Western Blot Analysis Cell Line: HCT-116 cells Concentration: 0.1 μM, 1 μM and 10 μM Incubation Time: 24 hours Result: NAG-1 was induced in HCT-116 cells in a dose- and time-dependent manner. Cyclin D1 expression was reduced at 10 μM. |
| In vivo study | Damnacanthal (10-100 mg/kg; oral administration; for 10-300 minutes; male ddY mice) treatment exhibits a significant antinociceptive effect in a dose-dependent manner in the formalin test. Administration of damnacanthal (100 mg/kg) shows significant inhibition of histamine-induced paw edema. Animal Model: Male ddY mice (5-6 weeks) injected with formalin or Histamine Dosage: 10 mg/kg, 30 mg/kg and 100 mg/kg Administration: Oral administration; for 10 minutes, 30 minutes, 60 minutes or 300 minutes Result: Significantly reduced the growth of human lung tumor without acute toxicity. |
1-Methoxy-3-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde - Reference Information
| Biological activity | Damnacanthal is an anthraquinone separated from the roots of Morinda citrifolia. Damnacanthal is a potent and selective inhibitor of p56lck tyrosine kinase activity. The natural Damnacanthal inhibited the autophosphorylation of p56lck and the phosphorylation of exogenous substrate, with IC50 of 46 nM and 220 nM, respectively. Damnacanthal is an effective apoptosis inducer with anti-cancer activity. Damnacanthal also has analgesic and anti-inflammatory effects in mice, and has antifungal activity against Candida albicans |
| Target | IC50: 46 nM; Apoptosis; Candida albicans |
| In vitro study | Damnacanthal has > 100-fold selectivity for p56 lck over the serine/threonine kinases, protein kinase A and protein kinase C, and > 40-fold selectivity for p56 lck over four receptor tyrosine kinases. Damnacanthal also demonstrates modest (7-20-fold), but highly statistically significant, selectivity for p56 lck over the homologous enzymes p60 src and p59 fyn . Damnacanthal (0.1-100 μM; 1-4 days; HCT-116 and SW480 cells) treatment results in a significant reduction of cell proliferation in a concentration- and time-dependent manner. Damnacanthal (1-50 μM; 72 hours; HCT-116 cells) treatment results in a significant enrichment in the number of cells in the S/G1 and G2/G1 phases at concentration of 50 μM. Damnacanthal (10 μM; 24 hours; HCT-116 cells) treatment significantly increases caspase 3/7 activity. Damnacanthal-induced apoptosis. Damnacanthal (0.1-10 μM; 24 hours; HCT-116 cells) treatment induces NAG-1 expression in HCT-116 cells. Cyclin D1 expression is reduced at 10 μM of Damnacanthal, whereas p21 and p53 does not alter their expression. PARP cleavage is seen at 10 μM Damnacanthal treatment only in HCT-116 cells, where NAG-1 is induced. Damnacanthal treatment for 2 weeks shows significant decreasing colony number in HCT-116 cells in a concentration-dependent manner. Damnacanthal-treated cells show a dramatic inhibition of clonogenic capacity. Damnacanthal-treated (1-50 μM; 48 hours) cells significantly inhibits the migration of HCT-116 cells in a concentration-dependent manner. Cell Proliferation Assay Cell Line: HCT-116 and SW480 cells Concentration: 0.1 μM, 1 μM, 10 μM, 100 μM Incubation Time: 1, 2, and 4 days Result: Resulted in a significant reduction of cell proliferation in a concentration- and time-dependent manner. Cell Cycle Analysis Cell Line: HCT-116 cells Concentration: 1 μM, 10 μM and 50 μM Incubation Time: 72 hours Result: Resulted in a significant enrichment in the number of cells in the S/G1 and G2/G1 phases at concentration of 50 μM. Apoptosis Analysis Cell Line: HCT-116 cells Concentration: 10 μM Incubation Time: 24 hours Result: Significantly increased caspase 3/7 activity. Western Blot Analysis Cell Line: HCT-116 cells Concentration: 0.1 μM, 1 μM and 10 μM Incubation Time: 24 hours Result: NAG-1 was induced in HCT-116 cells in a dose- and time-dependent manner. Cyclin D1 expression was reduced at 10 μM. |
| Cell Line: | HCT-116 and SW480 cells HCT-116 cells HCT-116 cells HCT-116 cells |
| Concentration: | 0.1 μM, 1 μM, 10 μM, 100 μM 1 μM, 10 μM and 50 μM 10 μM 0.1 μM, 1 μM and 10 μM |
| Incubation Time: | 1, 2, and 4 days 72 hours 24 hours 24 hours |
| Result: | Resulted in a significant reduction of cell proliferation in a concentration- and time-dependent manner. Resulted in a significant enrichment in the number of cells in the S/G1 and G2/G1 phases at concentration of 50 μM. Significantly increased caspase 3/7 activity. NAG-1 was induced in HCT-116 cells in a dose- and time-dependent manner. Cyclin D1 expression was reduced at 10 μM. Significantly reduced the growth of human lung tumor without acute toxicity. |
| In Vivo Study | Damnacanthal (10-100 mg/kg; oral administration; for 10-300 minutes; male ddY mice) treatment exhibits a significant antinociceptive effect in a dose-dependent manner in the formalin test. Administration of damnacanthal (100 mg/kg) shows significant inhibition of histamine-induced paw edema. Animal Model: Male ddY mice (5-6 weeks) injected with formalin or Histamine Dosage: 10 mg/kg, 30 mg/kg and 100 mg/kg Administration: Oral administration; for 10 minutes, 30 minutes, 60 minutes or 300 minutes Result: Significantly reduced the growth of human lung tumor without acute toxicity. |
| Animal Model: | Male ddY mice (5-6 weeks) injected with formalin or Histamine |
| Dosage: | 10 mg/kg, 30 mg/kg and 100 mg/kg |
| Administration: | Oral administration; for 10 minutes, 30 minutes, 60 minutes or 300 minutes |
Last Update：2024-04-09 02:00:00
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Product Name: Damnacanthal Visit Supplier Webpage Request for quotation
CAS: 477-84-9
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
CAS: 477-84-9
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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